Gobbler Hill, circa 1858 with an addition built in 1989, sits like a jewel atop one of the highest points in Kent County. Listed on the National Historic Registry, the transitional architecture is an excellent example of late Greek Revival to early Italianate. The property consists of four parcels totaling over 65 acres. Wildlife abounds on the fields of native prairie grasses, wild flowers, woods, approximately 20 tilled acres and a large pond. Impeccable attention was payed to maintaining the historic character of both the interior and exterior. From the Lincrusta wall covering, 19th century faux wood finishing, plaster medallions, white and sugar pine wood floors and crown molding on the 11 ft. ceilings to the monumental copper roof, the thoughtful restoration is stunning. The newer addition beautifully blends into the original section adding modern conveniences and natural light. The library boasts black walnut bookshelves constructed by a local craftsman. Well maintained grounds offer gardens, mature trees, a classic poured concrete in ground pool with inlaid tile and stunning views. This unique, lovingly restored piece of Kent County history is now looking for a new steward to guide it into its next chapter.

Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but high end modern upgrades, you will be living the life of luxury. Spacious rooms, magnificent views of the Chester River and your private dock with new boat lift, sandy beach, and stunning new saltwater pool. Exposed beams, scalamandre wallpaper, and multiple fireplaces. First floor owners suite featuring reclaimed pine flooring, private laundry area, walk-in closet, gas fireplace and remodeled bath with soaking tub. Second floor owner's suite with additional laundry area and remodeled bath. Breezeway to the garage. New irrigation system to all flower beds. New paint inside and out. House has had major remodels in 2000 and 2020. Town sewer. Not far from town, but the property has a private feel. Some interior images have been AI virtually staged for illustrative purposes. These images do not represent the property's current furnishings or decor.

PRICE REDUCED: Don't miss this rare opportunity. This special home offers spectacular and picturesque views of the Saint Michaels Harbor in addition to its prime location on one of Saint Michaels most desirable streets. Conveniently located near all of the in-town amenities and walkable to great restaurants, shops, brewery, winery, gallery, seasonal farmer's market, museums and more. This home has received a fresh interior painting, a deep cleaning and it is move in ready and ready to enjoy the Summer in Saint Michaels.216 E Chew Ave. is a 4-bedroom, 3 full bath and 1/2 bath home with the 1/2 bath on the first floor. One of the bedrooms and a full bath is a guest apartment with a kitchenette located over the 2-car attached garage. The guest apartment is accessible from the inside of the home or by a private outside entrance. The Primary Suite includes an updated en-suite Bath with double vanity, walk-in shower and private toilet. The Primary bedroom has room for a king-size bed, a walk-in closet, a north harbor view and access to the 2nd floor front porch. The 2 additional bedrooms have large closets, harbor views and individual access doors to the front porch. Both bedrooms share a large, updated bathroom with a combination tub/shower. The main part of the home is both comfortable and casual while at the same time stately and refined. The kitchen and eat in breakfast /dining area looks out over the Harbor and opens to the 1st floor porch and porch swing which is a great place to have your morning coffee. The kitchen has a great layout, granite counter tops, stainless appliances, a Viking paneled refrigerator and a walk-in pantry. The Dining room or living room has a harbor view as well and a central fireplace with attractive marble and millwork. The architectural marvel of this home is the Conservatory. It is a fantastic room for entertaining with a double height ceiling and intriguing structure. This was in use as a great room / family room. The back wall could also accommodate a large bar and flat screen if desired. If interested, a future owner might consider it for spacious ground floor master suite as double closets and laundry plumbing already exist in addition to plumbing for a wet bar. Two sets of French doors open to either the front lawn or side yard for entertaining and outdoor grilling and dining. The side yard has a southern exposure and paver patios for a dining set and a fire pit. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the beautiful sunrises and sunsets. Now offered at a REDUCED PRICE, this home also has the lowest price per square foot for a Luxury, Waterview, in town home (under $450), making it a comparatively excellent value. This rare combination of location, quality, amenities and value cannot be replicated in the Saint Michaels market. Do not miss the opportunity to enjoy all that is special about Saint Michaels that comes with this special home.

Waterfront living overlooking Still Pond Creek! Gently nestled into the woods on 5.67 acres of peace and nature, this special home is the ultimate dream getaway for relaxation and recreation. Enter this very private sanctuary surrounded by nature which offers a large, circular area accommodating parking for many guests. Upon entering the home, you will take in the elevated waterfront views from the light-filled great room with a soaring ceiling and a wall of windows. This space opens to a deck as well as a large screened-in porch that is the heart of the home all summer. It features a seating area to spend hours relaxing and enjoying the sounds of nature in complete privacy, and a dining table to watch the changing colors of the sky every evening. The open floor plan of the home is ideal for entertaining and offers waterfront views from nearly every room. The home features three bedrooms, three full baths, a loft office, a wood-burning fireplace, and a walk-out lower-level area with additional guest space and recreation area, including one of the full baths and additional large storage areas. Upstairs the primary suite is very private, with a renovated bath and beautiful water views. The home has many upgrades throughout, including beautiful hardwood decking on the decks and porch and new two-zone heating and cooling.  The property is surrounded by a native pawpaw patch, and each summer you will await the arrival of the many zebra swallowtail butterflies they host.  In the morning, wake to a beautiful sunrise over the creek, and listen to the many songbirds that pass through the property. The nearby eagle nest often leads to seeing them soaring overhead. At the waterfront there is a private sand beach where no other homes can be seen in any direction. Sunset is also a special time to sit down on the dock and enjoy the evenings. Stone steps lead down the path to the dock and water, first over a short raised boardwalk and then through a magical moss section, arriving at the private pier with a 8000lb boat lift, electricity, and approximately 4.0 ft MLW. Still Pond Creek, ideal for kayaking, fishing, boating, paddle boarding, wake boarding, and more, makes this a water lover’s dream home. The location is ideal - just around the corner from the bay yet just beyond the section frequented by those coming to experience the charm and deep anchorage of the creek. Located in the highly sought-after community of Kinnaird’s Point with a community boat launch, beach, and pavilion, high-speed internet, and located just outside of Chestertown - 59 miles to Annapolis, 87 miles to DC, and 86 miles to Philadelphia. Historic Chestertown on the Chester River, home of Washington College, is located just 10 miles away and offers great restaurants, bars, shopping, an outdoor Farmer’s Market, annual celebrations including the Chestertown Tea Party, Sultana Downrigging Festival, and much more. Please do not drive in the driveway without an appointment. The property is available furnished, excluding art and personal items. The structure sits well above the water and is not in a flood zone. Full home, septic, and water reports available online.  Owner is a licensed PA realtor.

This is the quintessential Eastern Shore Waterfront Estate to turn into your legacy property. Sitting on over 12 acres just minutes from the Bay Bridge, this substantial craftsman built in 1914 once served as the primary residence for one of the lead engineers for the Pentagon, Jefferson Memorial, and other DC marvels due to its balance of proximity to the city and quality of life. Lifestyle amenities have improved since then with nationally renowned Queenstown Harbor Golf Resort and the marinas/dining options in Kent Narrows all minutes away. Privacy is paramount here with a wooded and gated entry lane but without sacrificing access due to the exit on Route 50 still less than a mile away. The sweeping views here are unmatched with the protected lands of Eastern Neck Wildlife Refuge across the Chester from the residence also guaranteeing this peace and tranquility for years to come. The home itself is a historic masterpiece with hardwood floors, hand blown glass windows, and grand center hall staircase. The connection with the water is celebrated here with multiple sunrooms boasting big water views for those special moments. A rough cut timber 2 car garage and workshop provides old Eastern Shore charm. Wildlife here is abundant for the outdoorsman and nature lover due to it being one of the first large parcels after crossing through the hustle and bustle of Kent Island. Invest wisely while improving your quality of life with your own waterfront sanctuary to create those special memories for generations.

A Rare Waterview Masterpiece Designed for the Ultimate Boating Lifestyle. Set on 1.376 acres with breathtaking water views and unforgettable sunsets, this one-of-a-kind contemporary residence delivers luxury, functionality, and resort-style living at every turn. Thoughtfully designed with the boater in mind, this exceptional home offers expansive entertaining spaces, refined finishes, and outstanding access to boating amenities. The main level showcases a dramatic living room with gas fireplace and sweeping water views, a dining room opening to the rear deck, and a stunning gourmet kitchen featuring quartzite countertops, a grand center island, Wolf 5-burner gas stove, steam oven, convection oven, butler’s pantry, and an additional pantry/storage area with refrigerator. A screened-in porch just off the kitchen creates the perfect space for relaxed water view living. Also on this level are a hall bath, office or sitting room, main-level laundry, and a luxurious primary ensuite with small deck with stunning views, double vanities, jetted tub, and a separate shower and toilet area. The second level is ideal for hosting, offering three bedrooms with 2 full baths, plus two additional sleeping areas thoughtfully designed for guests. The fully finished lower level continues the luxury with a gym, room of choice office/bedroom with full bath, additional laundry hookup, spa-like bathroom with double vanities and an oversized shower, and a rear entry perfectly suited for coming in off the water. Outdoor living is nothing short of spectacular, featuring a professionally landscaped rear patio with water feature, firepit, garden irrigation, and automatic timers. A rear garage and workshop provide ample space for water toys, gear, and golf carts. Additional highlights include a deeded boat slip with two boat lifts, 90-amp electric vehicle charger, whole-house humidifier, three-zoned HVAC, Pella windows, architectural roof (2024), automatic water shutoff system (Flow Logic), and all appliances included. An exclusive opportunity to acquire the adjacent 1.245-acre parcel, offered separately, featuring a deeded boat slip and lift, with right of first refusal extended to the purchaser. This extraordinary property offers a rare blend of luxury, privacy, and elevated water view living. Truly one of a kind—schedule your private showing today.

Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/- of waterfrontage and deep-water access, this 4-bedroom, 3-bath brick Cape Cod invites you to enjoy the very best of waterfront living.Unlike many waterfront properties, the level lot provides easy access from the home to the water and private pier—no steep banks or long flights of stairs to navigate. Whether you enjoy boating, kayaking, fishing, crabbing, or simply relaxing by the water, this property makes it easy to embrace the Eastern Shore lifestyle.Inside, you'll find more than 2,200 square feet of comfortable living space designed to capture the stunning river views. A charming four-season room with brick flooring and panoramic water views is the perfect place to enjoy your morning coffee year-round, while the screened porch is ideal for summer crab feasts and outdoor entertaining. At the heart of the home, a wood-burning brick fireplace that creates a warm and inviting atmosphere.The flexible floor plan includes a main-level bedroom and full bath, ideal for guests or one-level living. Upstairs, the primary suite serves as a peaceful retreat, featuring breathtaking river views, abundant natural light, and a private ensuite bath with double vanities and a tiled shower. Two additional generously sized bedrooms and another full bath provide ample space for family and visitors.Recent improvements include a new roof in 2020 and an electric vehicle charger installed in the attached garage in 2025. An irrigation system serves both the front and rear yards, and the property is located outside the flood plain, so flood insurance is not required.Tucked away near the end of a private road, this serene setting feels calm and peaceful while remaining just minutes from Chestertown's shops, restaurants, marina, and popular farmers market. Enjoy daily visits from eagles, ospreys, herons, owls, deer, and other wildlife, all from your own backyard.Whether you're searching for a full-time waterfront residence or the perfect weekend escape, this rare Chester River property offers the beauty, tranquility, and lifestyle that makes Maryland's Eastern Shore so special.

Gorgeous waterfront home! Rancher, one level living on over 2 acres in Royal Oak. Get ready, properties like these don't come around too often!

More than a home, this is truly a recreational property and boater's paradise. Nestled on a promontory point above Still Pond Creek and just a short drive from historic Chestertown, this house was designed by iconic architect Peter Newlin to provide a coziness and connection to nature that embodies the Eastern Shore lifestyle. Jutting out from the bulkhead designed the Army Corps of Engineers, the dock awaits you for boating adventures and quick access to the Chesapeake Bay directly from the protected waters of Still Pond Creek. Life slows down while appreciating the water and wildlife from the deck. The spacious screened porch is perfect for crab feasts with unmatched views. A lane for vehicles and also a winding walking path leads you down to the private beach where memories and tans are made. The great room boasts vaulted ceilings with exposed beams and flows out with sliders and a side door to the screened porch and deck for indoor-outdoor living. A trio of picture windows and the wood burning fireplace are perfect for cuddling up and looking out over the water on cool winter days. There are two bedrooms and full bath on the main level and a primary suite with ensuite bathroom, vaulted ceilings, and walk in cedar closet upstairs. The large walkout basement is the perfect space for the kayaks, bikes, and other toys that come with living on the Eastern Shore. The land itself is low maintenance but expansive allowing for calming hikes and relaxation in nature. Invest wisely in this irreplaceable asset less than 2 hours from Washington DC, Philadelphia, and Baltimore.

Some Day has arrived. Tucked within 38 rolling acres near Betterton Beach and the Chesapeake Bay, this private equestrian retreat offers space to slow down, reconnect with nature, and awaken to birdsong across the fields. The inviting three-bedroom, three-and-a-half-bath home features a first-floor primary suite, private study, and an attached two-car garage with a loft roughed in for a potential caretaker’s or guest suite. Paddocks, riding trails, a sand ring, five-stall stable, and four-bay machine shed complete the equestrian setting, while more than half the acreage is currently tilled under a farm lease. Peaceful and private, Some Day Farm is a place to breathe deeply and live fully. This property is an estate and is being sold as is.

Some Day has arrived. Tucked within 38 rolling acres near Betterton Beach and the Chesapeake Bay, this private equestrian retreat offers space to slow down, reconnect with nature, and awaken to birdsong across the fields. The inviting three-bedroom, three-and-a-half-bath home features a first-floor primary suite, private study, and an attached two-car garage with a loft roughed in for a potential caretaker’s or guest suite. Paddocks, riding trails, a sand ring, five-stall stable, and four-bay machine shed complete the equestrian setting, while more than half the acreage is currently tilled under a farm lease. Peaceful and private, Some Day Farm is a place to breathe deeply and live fully. The property is an estate and is being sold as is.

Located in the heart of St. Michaels' historic district, this adorable cottage has a rare zoning that allows for short term vacation rental, and it has been a very successful one. The current owner has great reviews and reports revenues of $65,000 in 2025. There is excellent bedroom separation, with one bedroom on the first floor in the back, the other on the second floor in the front. The kitchen was recently renovated and the heating/air conditioning was replaced in 2024. The yard is spacious, with a fenced oyster shell yard featuring a firepit and off street parking for two cars. This home is turnkey - all furnishings and short term rental supplies included. Don't miss this rare opportunity!

Welcome to this luxurious, waterfront townhouse in the beautiful town of St. Michaels! This is the absolute total package, offering turn key comfort in a centralized location, allowing you to maximize everything the eastern shore has to offer. Enjoy the views of the majestic Miles River, boating from your personal, deeded boat slip, or walk across the street to the Eastern Shore's most premier golf course! This expansive unit offers premium upgraded finishes, a first floor ensuite bedroom, fireplace, and endless enhancements, including new windows and completely new HVAC system. Minutes to town for shopping or award winning dining experiences. This is truly the perfect waterfront, low maintenance getaway that is sure to check all of the boxes of a dream home!

**Seller to Provide $25,000 Credit for Desired Updates with a Full Price Offer.**The Sally Harris Mill House was once part of the Bloomingdale Estate is one of the remaining 18th Century masterpieces on the Eastern Shore. This peaceful farmette boasts over 31 acres with a blend of open pasture and wooded seclusion. The property sits on the Western banks of Madam Alices Branch, a tributary of the Wye River. Mature evergreens line the entrance creating a dramatic feel and historic charm is displayed throughout the home with 5 fireplaces, Flemish bond brickwork, and a gambrel roof. Modern amenities have been incorporated with the 2 story North wing which was completed around 2000 to include a first floor primary suite with en suite bathroom, makeup room, and 2 separate walk-in closets on the first floor and 2nd floor family room. The updated kitchen, partially finished basement with kitchenette, and heated pool are also highlighted upgrades. Outdoor living is celebrated here with a screened in rear porch for dinners in nature, a front porch to sit and watch the wildlife, and pool deck for making memories. Bring your machines and toys because there is plenty of storage in the outbuildings. The 2 story machine shop has been impeccably maintained and is perfect for any type of project. The open pasture would be perfect for horses and though they haven't been maintained in a few years, the forest contains nature trails for disconnecting from the hustle and bustle or hunting opportunities. This is your chance to make a piece of Eastern Shore's history your own peaceful retreat.

Nestled on 1.3 private wooded acres in the sought-after waterfront community of The Downs, this distinctive Deck House offers a rare opportunity to own a home designed to embrace its natural surroundings. Characterized by dramatic walls of glass, vaulted cedar ceilings, and an open, light-filled floor plan, the home seamlessly blends indoor and outdoor living.The main level features hardwood floors, an open-concept living, dining, and kitchen area, and a striking wood-burning brick fireplace as its centerpiece. A wraparound porch and expansive decking provide the perfect setting for morning coffee, outdoor dining, or simply enjoying the peaceful wooded landscape from every angle. Enhancing the home's modern livability is an upgraded audio/visual system featuring in-wall speakers throughout the interior and outdoor Sonos speakers, all conveniently controlled from a smartphone for effortless entertaining and everyday enjoyment.The finished walkout lower level offers exceptional flexibility with space for additional bedrooms, a home office, recreation room, fitness area, or guest accommodations.Outside, the backyard retreat is designed for entertaining and relaxation, featuring a pool, hot tub, and generous outdoor living spaces surrounded by mature trees and natural beauty. While thoughtfully maintained, the home also presents an incredible opportunity for its next owner to update and personalize the space, creating a truly one-of-a-kind retreat tailored to their vision. Pool and hot tub sold in as is condition.Residents of The Downs enjoy an unparalleled waterfront lifestyle with access to a community marina, boat slips (subject to availability and application), swimming pool, tennis courts, kayak storage, clubhouse, and water privileges. Conveniently located just minutes from Downtown Annapolis, Baltimore, and Washington, D.C., this property combines architectural character, privacy, and endless potential in one of Annapolis' most desirable communities.

Welcome to 13532 Rustling Oaks Drive: where meticulous pride of ownership truly shows on this classic Cape Cod in the land of pleasant living on the Eastern Shore. Situated on over an acre of land with towering pines providing excellent shade and privacy, this 5 bedroom, 5,500+ square foot home has been recently upgraded and offers something for the whole family. 10 foot ceilings, hardwood floors, arched hallways, crown moldings, columns, chair rails, are just a few of the timeless interior finishes while a brand new saltwater gunite pool elevates the exterior space. Inside, an expansive first floor primary suite offers total main level living and complete privacy. With a tray ceiling, bay window and double walk-in closets, it is a retreat in its own; punctuated by an updated ensuite bath with double vanity, soaking tub, and oversized glass walk-in shower. The true heart of the main level is the upgraded kitchen and living room areas. These large complementing spaces are perfect for entertaining and everyday living. The kitchen has all new stainless steel appliances including a double wall oven and is finished with wood cabinets and granite countertops. The large island has a propane cooktop and overhanging bar seating. A breakfast area looks through a large bay window to the back yard. A new wood burning stove insert with wood mantel is the centerpiece of the living room just off the kitchen. A formal dining room and separate laundry/mud room complete the first floor. The main living area seamlessly flows into everyone's favorite space: the back yard, anchored by a brand new saltwater gunite pool and sweeping patio with lounging, grilling and fire pit areas. An additional screened-in porch with a tv is perfect for summertime crab feasts or morning coffee. Back inside, the basement is another world of its own with 9 foot ceilings and over 2,000 finished square feet. A 2nd full kitchen opens the possibilities to a private guest space or mother-in-law suite. There is a large game area, a private home office, a 5th bedroom with full bath and an unfinished utility space with room for more storage or workout equipment. Moving upstairs to the 2nd floor, one will find an additional primary bedroom with ensuite bath, two more generously sized guest bedrooms, a shared bath and a comfortable reading area atop the stairs. In addition to the two-car attached garage, a detached two-car garage with space above offers additional storage and workshop potential. A large garden shed and underground sprinkler system completes the backyard. A few of the recent updates include a saltwater gunite pool (2024), all new stainless steel kitchen appliances (2024), updated primary bath (2025), first floor dual-fuel 5-ton high efficiency heat pump (2025), fireplace wood stove insert (2023), leaf gutter guards (2025). Minutes away from a public boat ramp serving the picturesque Wye River and the enduring beauty of the Wye Island Nature Preserve. Major marinas are close by at Kent Narrows, St Michaels, or Oxford. This centrally located Eastern Shore getaway serves the lower beaches and the Chesapeake's tributaries well yet is still an easy commute to Annapolis, Baltimore or D.C. 10 minutes to downtown Easton and all the shopping you might need. The property across the street is open community space and will not be built upon. This tastefully updated and diligently maintained home offers a unique blend of amenities and functionality for the laid-back Eastern Shore lifestyle. Much more info and professional photos to come. Stay tuned!!

Serene Waterfront Retreat on Fairlee Creek is nestled in the tranquil woods of a private community just 10 minutes from the charming shops, museums, and dining of Chestertown, and the neighboring waterfront oriented town of Rock Hall. This stunning 4-bedroom, 2-bathroom waterfront home on Fairlee Creek offers the ultimate blend of seclusion, modern luxury, and effortless outdoor living. Imagine stepping out to launch your boat or kayak, or maybe just casting a line from your own private pier and floating dock—newly installed in 2025. Step inside this thoughtfully updated retreat, where every detail whispers move-in ready. The upper level welcomes you with an open-concept living area, dining area, and kitchen, all flowing outside onto a partial wraparound deck perfect for sunset cocktails or al fresco family meals. Cozy up by the wood-burning stove in the living room on crisp evenings, or entertain in the heart of the home with a gas range and new quartz countertops in the kitchen. The upper level bedroom invites you to start your day with private deck access and creek views. Venture downstairs to the versatile lower main level, featuring three generously sized bedrooms—one with direct waterfront vistas and french doors to the expansive lower deck and lush yard. The flexible family room adapts to your lifestyle, whether as a cozy office, kids' play haven, home gym, or media lounge, all with easy access to the outdoors. Recent enhancements shine throughout: fresh paint graces the entire house and decks (2025), while a brand-new roof installed on October 6 of this year ensures peace of mind for years to come. A new central HVAC system for the lower level, efficient mini-splits on the upper level, and bathroom remodels were all completed in September of this year. The septic system was replaced in 2021 with new BAT septic system, rated for 4 bedrooms. Outside, the magic truly unfolds. Extensive hardscaping creates an entertainer's paradise, anchored by an inviting fire pit for starry-night gatherings, barbecues, gardening, or simply soaking in the creek's serene rhythm. Your private pier and floating dock make water access effortless—launch kayaks, tie up your boat, or just watch wildlife drift by. Fairlee Creek provides a short trip direct to the Chesapeake Bay. Want a little less privacy? As a resident of this exclusive community, you unlock access to the Safe Harbor at Great Oak Landing Marina for a modest annual fee. Walk, ride a golf cart, bicycle, or drive to the marina and golf course and enjoy a resort-like lifestyle with a sparkling pool, seasonal waterfront restaurant, sandy beach, and golf course. Boat slip availability? Contact Safe Harbor directly to secure your spot at the marina. Enjoy priceless privacy in a wooded waterfront wonderland, with upgrades galore and the Chesapeake Bay lifestyle at your doorstep. Schedule your private tour today and claim your water-side paradise!

New Construction to be Complete Summer of 2026

Elevated coastal elegance is displayed in this waterfront perched on the banks of Mill Creek. An open floor plan, radiant floor heating, high ceilings in the great room create an ambience conducive to a luxury weekend retreat or full time residence. Water views are celebrated from nearly every inch of the home and the large windows allow for a deep connection with nature. Outdoor living is a highlight with a covered waterfront screened in porch for crab feasts, fire pit with seating providing sweeping views of Mill Creek, and expensive rear decks on each floor. Two bedrooms on the main level make one floor living a breeze including the primary with ensuite bathroom and walk in closet. Stainless steel appliances adorn the kitchen. The great room is impressive, creating a magnet effect for family and friends. Upstairs has an bonus room perfect for your home office. This is a boater's paradise with direct access to the bay within minutes but protected waters at your shoreline. The private dock includes an additional floating pier suitable for kayak excursions. The front yard has thoughtful planting, pea gravel driveway, and potting shed. Across the lane is an additional lot that comes with the property and is currently used for storage. Feel a connection with the Eastern Shore and its waterways with this high end waterfront sanctuary just 15 minutes from the shops, galleries, and restaurants of historic Chestertown.

Welcome to 329 Price Drive, located in the prestigious Estates at Cedar Lane within the highly sought-after Appoquinimink School District.Rarely do estate homes of this size and caliber become available. Situated on a sprawling ½-acre lot, this stunning brick-front residence offers approximately 3,825 square feet of living space, with an enormous unfinished basement that provides the potential to expand to nearly 6,000 total square feet.Step inside to a grand two-story foyer that sets the tone for the entire home. The main level features a formal living room, formal dining room, private home office, double coat closet, and a convenient powder room. The centerpiece of the home is the breathtaking two-story family room highlighted by a floor-to-ceiling stone fireplace.The chef’s kitchen is truly a dream, complete with custom farmhouse-style cabinetry, granite countertops, ceramic tile backsplash, stainless steel appliances, a massive center island, and a bright and inviting morning room. Additional main-level conveniences include a mudroom with double-door pantry and a spacious walk-in laundry room.Upstairs, you’ll find four generously sized bedrooms and three full bathrooms. Bedrooms 1 and 2 share a Jack-and-Jill bath, while Bedroom 3 enjoys its own private en-suite. The owner’s suite is a true retreat, featuring a tray ceiling, sunken sitting area, expansive walk-in closet, and a luxurious spa-style bathroom with dual vanities, soaking tub, separate shower, and private water closet.The unfinished walkout basement offers endless possibilities, already equipped with a rough-in for a full bathroom and a double-wide staircase exit—perfect for creating additional living space such as a home theater, gym, recreation room, or guest suite.Outdoor living is just as impressive. Step through the morning room to a custom-built 20x26 oversized deck, featuring dual staircases, exterior lighting, and a gazebo, making it ideal for entertaining or relaxing.Additional upgrades by the current owner include:Hardwired security camera system with monitor (mobile accessible)Full-lot irrigation systemCustom trim and detailed woodwork throughoutProfessionally installed epoxy garage flooringBlack aluminum fencing enclosing the rear yardOpportunities like this are rare—a true estate home on a premium lot in Appoquinimink School District offering space, upgrades, and endless potential.

Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.

Built in the early 1900s and thoughtfully renovated over the past 20 years, this charming home beautifully combines historic character with modern amenities. Situated on a half-acre lot, the property features 3 bedrooms with the potential for a 4th bedroom, along with 3.5 bathrooms. Each bedroom includes its own private bath, and the bedrooms offer access to relaxing balconies. The updated kitchen is equipped with granite countertops, stainless steel appliances, and tile floors. Hardwood flooring that continues throughout the home. Outside, the property also includes a potting shed and a machine shed, providing additional storage and workspace. A standout feature is the impressive 1,500-square-foot attached garage. This two-story space includes three garage doors, three passenger doors, and a dedicated office area, offering exceptional versatility for hobbies, work, or storage. With its timeless old-world charm and carefully integrated updates, this home offers the perfect blend of classic style and modern comfort.

Welcome to Windwood: where meticulous pride of ownership truly shows on this classic Cape Cod on nearly 10 acres of serene, private land. With an expansive 4-bedroom main house and separate guest cottage; this home is perfect for a multi-generational family who are looking for separate spaces or for a family looking to generate more income by utilizing the guest house as a rental. This home really epitomizes quality 1960's construction and craftsmanship: solid brick and cedar siding, southern pine hardwood floors throughout, elegant keyhole crown moldings, a wonderful dining room fireplace, built-in shelving and cabinets, timeless dormers, and so much more. Coming up the circle drive you are received by a peaceful front porch; perfect for enjoying summer breezes and sunsets. Inside you are greeted to a welcoming foyer with a formal living room to your right and massive dining room to your left complemented by a wood-burning fireplace with intricate wood mantle. Moving back you will find the private main-floor primary suite with ensuite and large walk-in closet. The first floor further features a TV room and a recently renovated sun-room bump. out. Continuing on, the spacious kitchen with breakfast area was renovated in 2021 and now features honey-oak built-ins, custom cabinets, granite countertops, stainless steel appliances, propane or electric stove, a generously sized island with overhang seating, and LVP flooring. As you take the wide staircase upstairs you will find more gleaming hardwood floors that were just refinished. The second floor has three generously sized bedrooms; each with large closets and a smaller office space. Each end of the second floor features large attic storage areas. The full basement is partially finished with a spacious rec or workout room with a wood burning stove and new LVP floors. Across the brick breezeway, the guest house has also been recently renovated including all new kitchen appliances, walnut cabinets, washer/dryer, new floors, and upgraded bath. In front of the guest house is an attached two-car garage with additional areas for storage and tools. The backyard is a gardener’s dream and is fully fenced for the dogs and/or little kids. A small garden area, pergola and small fishpond complete the peaceful surroundings. Several walking trails have been cut out throughout the woods where you will find a large woodshed with plenty of storage. This wonderful property has so much to offer, you won’t want to miss it. Sellers have a $450,000 assumable VA Loan at a 2% interest rate. Recent updates include: roof tune up, exterior paint, interior hard floor refinish, interior paint, hvac service, and more.

Welcome to 101 Thicket Court in the sought-after Willow Branch East community, built with exceptional craftsmanship by Mike’s Custom Homes.This stunning 4-bedroom, 3.5-bathroom residence offers over 3,400 square feet of thoughtfully designed living space on a 1.25-acre lot. From the moment you arrive, the gorgeous custom front door makes a bold statement, setting the tone for the elegance within.The home’s exterior, finished in the serene Sea Grass siding, complements its timeless curb appeal. Step inside to discover a bright and open floor plan with high-end finishes throughout. The heart of the home features a kitchen with quartz countertops, custom cabinetry, and premium fixtures, seamlessly flowing into spacious living and dining areas—perfect for both everyday living and entertaining.Retreat to the private owner’s suite with a bath, while three additional bedrooms provide comfort and flexibility for family or guests. The walkout basement offers endless possibilities for recreation, storage, or a future home gym or theater. Rear 35x20 DeckSituated on a generous lot, this property offers both privacy and space to enjoy outdoor living. Every detail has been considered to bring together comfort, style, and functionality in a home you’ll be proud to own.

Discover the charm of this exquisite transitional Victorian home nestled just off the beaten path in downtown Chestertown. Built in 2011, this stunning residence boasts meticulously maintained living space, featuring an open floor plan that seamlessly blends comfort and style. The interior showcases beautiful wood floors, exposed beams, and an abundance of natural light from skylights and double-pane windows, creating an inviting atmosphere throughout. The owner's suite is located on the main floor with a beautiful new ensuite bathroom. On the second floor, you will find another living area with an additional 3 bedrooms and bathroom. Cozy up in the living area by the Vermont Castings pellet stove, perfect for creating lasting memories. The main floor laundry adds convenience to your daily routine. Step outside to enjoy the wrap-around porch, screened porch, and balcony, all overlooking the beautifully landscaped yard, ideal for entertaining or simply unwinding in your private oasis. The attached garage and paved driveway provide ample parking for you and your guests. Encapsulated crawlspace with room for storage. This home is just a short walk from historic downtown with all of the amenities like shopping, dining, farmers market and theater.

This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded boat slip - #49 - just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

A BOATER'S DELIGHT, this waterfront rancher in Chester River Beach is a small slice of paradise! Enjoy deep, protected water (5ft mlw) and tranquil views of Winchester Creek. As you enter the home, you'll be captivated by the open concept kitchen and living room with expansive water views. The updated kitchen showcases white cabinets and granite countertops. The fully conditioned four season room is perfect for enjoying the views all year long and has brand new high quality windows and slider door! Features 3 bedrooms, 2 full bathrooms and an expansive 2 car garage that's large enough to fit a 25 foot boat w/ trailer inside. The primary ensuite bathroom has been gorgeously updated with floor to ceiling Italian tile. Brand new wood grain tile is featured throughout the main living areas. New roof, new HVAC, and new appliances! The pier features a 15,000 lb boat lift and deep water! Chester River Beach features a community waterfront park, picnic area and pavilion as well as a boat launch and community pier with boat slips. Enjoy the convenience of being minutes from the Kent Narrows dining and entertaining experiences by car or boat! 10 minutes to the Bay Bridge! Schedule your showing today!

Private Oasis on 7.55 Acres — A Rare Opportunity for Privacy and ComfortExperience exceptional privacy and refined living in this beautifully appointed 3-bedroom, 2.5-bath ranch home, thoughtfully designed for both comfort and functionality. Nestled on 7.55 meticulously landscaped and irrigated acres, this property offers a peaceful retreat with scenic views and unmatched seclusion.Inside, the home features a spacious living room anchored by a stunning stone fireplace, creating a warm and inviting atmosphere. The expansive kitchen is ideal for entertaining, offering a large center island, walk-in pantry, and ample cabinetry. A generous laundry room includes a utility sink and dedicated folding area for added convenience.The oversized sunroom provides year-round enjoyment and opens to an impressive hardscape patio complete with a stone wood-burning fireplace—perfect for outdoor gatherings and relaxation.The luxurious owner’s suite serves as a private sanctuary, featuring a large walk-in closet, whirlpool tub, walk-in shower, dual vanities, and an adjoining flex space ideal for a home office or private sitting room. A split floor plan offers two additional bedrooms connected by a Jack-and-Jill bathroom, ensuring comfort and privacy for guests or family.Additional highlights include a whole-house generator, an attached three-car garage, and a substantial stick-built workshop equipped with heat and water—ideal for hobbyists, collectors, or equipment storage. An equipment run-in provides even more functional space.This exceptional property seamlessly blends privacy, luxury, and practicality, making it a rare opportunity for those seeking a serene lifestyle without compromise.

Handsome farmhouse on 36 acres. House maintains much of its original character. Spacious rooms and beautiful views.

Thoughtfully designed and built in 2017, this private retreat sits on nearly 7 peaceful acres just 5 minutes north of historic Chestertown and 30 minutes from Middletown, Delaware. Surrounded by farmland and mature landscaping, the property offers the perfect balance of modern comfort, flexibility, and quiet Eastern Shore living. The heart of the home is the stunning chef’s kitchen featuring cathedral ceilings, top-of-the-line appliances, a large center island, and separate pantry. The kitchen flows into the family room with a propane fireplace and French doors leading to the rear screened porch where you can take in views of the yard and surrounding countryside. The main level primary suite offers a spacious bathroom and oversized dressing room closet. A second main level bedroom provides access to a full bathroom and dedicated office. An additional bonus room on the main level offers flexibility for dining, hobbies, crafts, or running a business from home. Upstairs, you’ll find two additional bedrooms and a full bathroom. The partially finished walkout basement expands the living space even further with a full bathroom and flexible recreation or guest area with direct access to the backyard. Additional features include an oversized detached two-car garage with attic storage above, numerous garden beds throughout the property, and a peaceful setting that offers privacy, space, and room to truly enjoy the outdoors.

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries, and restaurants, it offers the perfect balance of walkability and tranquility on one of the district's quietest streets. The thoughtfully designed layout makes excellent use of every square foot, while tasteful updates fill the home with natural light. A spacious screened porch extends from the dining room, offering a peaceful place to relax and enjoy the character of the neighborhood. The fenced backyard is a gardener's dream, featuring lush landscaping, vibrant plantings, and beautiful hardscaping that create a private outdoor sanctuary. A rear entrance with off-street parking adds everyday convenience while preserving the home's charming streetscape. This exceptional historic property offers an outstanding lifestyle less than two hours from Washington, DC, and Philadelphia.

Built in 1780/1840, Highcroft is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor and a long driveway for tons of off-street parking. 3 bedrooms, 4 full baths and 1 half bath. Primary bedroom has his and hers private baths. 8.2 kw solar array on the garage. EV level 2 charger. Easy room flow from front to back for entertaining. Just steps to restaurants, bars, and shops. This is an ultra efficient green house.

This immaculate, 5-bedroom, 3-bath Colonial is ideally positioned on the coveted Bennett Point peninsula, set on a private 2+ acre partially wooded homesite. Thoughtfully upgraded inside and out, the home now offers smart home functionality, fresh interior paint, and a truly move-in ready experience. Outdoor living shines with a heated saltwater pool, elegant paver patio, and built-in gas fire pit—enhanced by privacy fencing, professional landscaping, and curated lighting. A shed provides stylish storage for pool and lawn essentials. Inside, the chef’s kitchen flows seamlessly into the dining area with slider access to the screened porch—ideal for elevated entertaining. Wood-look tile floors anchor the main level, which also includes a first-floor bedroom with full bath, a sun-filled family room, and updated lighting throughout. Upstairs, the spacious primary suite offers a walk-in closet and en-suite bathroom, complemented by three additional generously sized bedrooms and a full hall bathroom. An oversized driveway provides ample parking. Enjoy nearby water access at Bryantown Landing on the Wye River. Only minutes to Prospect Bay Country Club and Queenstown Harbor Golf Club. Easy commuting access to Easton, Kent Island, and Annapolis. A refined blend of privacy, modern comfort, and Eastern Shore lifestyle—this exceptional home is ready for its next chapter.

We are accepting backup offers and will allow showings. Perfectly situated on over an acre in a peaceful Centreville setting, this expansive custom-built home offers more than 4,000 square feet of beautifully designed living space across three finished levels, combining comfort, functionality, and exceptional value.The main level is ideal for both everyday living and entertaining, featuring a formal dining room and a gourmet kitchen with center island, dual wall ovens, induction cooktop, walk-in pantry, and sunlit breakfast nook. Just off the kitchen, the inviting family room includes a pellet stove, wet bar, and oversized sliding doors that open to a screened-in porch and spacious deck, creating seamless indoor-outdoor living.Upstairs, the oversized primary suite serves as a private retreat, complete with a propane fireplace, dual walk-in closets, and a spa-inspired bathroom featuring a jacuzzi soaking tub and rainfall shower. This level also includes two additional bedrooms, a large bonus room with pellet stove, a full bathroom, and a conveniently located laundry room.The third floor offers two additional versatile bedrooms and another full bathroom, perfect for guests, home offices, or hobby spaces.Outside, the property truly shines. Enjoy a fully fenced yard on over an acre, an oversized attached two-car garage, a detached two-car garage/workshop, storage shed, and a partial whole-house generator. With no HOA, you have the freedom to fully enjoy the property while still being just minutes from downtown Centreville, local shops and dining, Route 301, and only 13 miles from the Bay Bridge for an easy commute.A solar energy system is installed on the home, helping offset utility costs. This exceptional property offers size, privacy, and versatility rarely found at this price point in Centreville.

Nestled in the serene Orchard Hill community, this stunning Craftsman-Colonial offers 3,735 sq. ft. of luxury and comfort. The open, light-filled floor plan showcases rich hardwood floors and elegant finishes throughout.The gourmet kitchen features upgraded countertops, pecan wood-stained cherry cabinetry, stainless steel appliances, including double ovens, a gas cooktop, and a tankless water heater. It opens to the family room with a cozy corner gas fireplace—perfect for entertaining or relaxing.The main level includes an office, primary suite with a large bath and walk-in closet, an additional bedroom and full bath, and a dedicated laundry area. A screened-in porch off the main floor provides a peaceful space to enjoy morning coffee or evening gatherings surrounded by nature. Upstairs offers an open sitting area with window seat, two additional bedrooms, and a full bath.Set on a beautifully landscaped 2.81-acre lot backing to trees, this property provides a private outdoor retreat. Additional highlights include a side-entry garage, paved driveway, and outbuilding for extra storage.Experience the best of Orchard Hill living—where quality, comfort, and natural beauty come together.

Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside - no flood insurance needed. Enter the house through a split foyer with a few steps up to the main level and into the great room with the central kitchen, dining and living areas. The master suite is located on one end of the main level and features a large walk-in tile shower and a small private deck. The other end of the main level features a vaulted sunroom, a great spot to commune with nature or host the family crab feast. The lower walk out level offers a family room with a wood stove, two bedrooms, a full bath, a laundry room, and outdoor access. 2.5-3' MLW Buyer to verify. See Documents for Seller updates plus info on Association benefits. New roof added in 2021 and a BAT septic system was installed in 2023. Property has been well maintained but is being sold AS IS.

Welcome to 105 Pegasus Court- Spacious and beautifully updated, this 5 bedroom, 4.5 bath home is tucked away on a quiet cul de sac in the highly sought after Clairborne community in Appoquinimink School District. Designed for both comfort and functionality, the home features numerous upgrades throughout, offering a move in ready experience with modern finishes and thoughtful details.The expansive layout provides generous living and entertaining spaces, including a well-appointed kitchen, large bedrooms, and multiple living areas ideal for both everyday living and hosting guests. The fully finished basement offers a bedroom, full bathroom, living room, workout area and full bar. The master suite provides a private retreat with ample space and a luxurious en-suite bath.Step outside to your own backyard oasis, complete with an in-ground pool and firepit area perfect for summer gatherings or relaxing weekends at home. Major updates add peace of mind, including a newer roof, hot water heaters and a 2 year-old HVAC system, ensuring efficiency and long term value.Combining space, upgrades, and a prime location, this home delivers the ideal blend of convenience, privacy, and lifestyle. It won’t last long! *Seller is a licensed real estate agent.

An impeccably maintained, perfectly positioned two bedroom, two and one-half bath condo featuring one of the best vistas of Chestertown and the Chester River. Here, body, mind, and spirit naturally align - it's simply impossible not to feel balance. River House, with only five private residences, occupies the best real estate within this prized, friendly and well managed neighborhood called Chester River Landing. Historic downtown Chestertown and the Chester River Yacht & Country club are less than 2 minutes away, when you need a break from your enclave that includes marina, grill patio, crabbing/fishing pier, beach area for kayak launch, waterfront green space with fire pit, community garden, and pool with pool house. Unit 201 includes a nearby 1 car garage with overhead storage racks and a deeded premium boat slip (A7) A unique feature of this home is a custom HVAC and air quality system, ideal for anyone with seasonal allergies, chemical sensitivities, or just appreciative of quality air and healthy living. New GE range, LG and 03 Pure Eco Laundry System installed 2025. (Warranties convey). The lobby and all common areas have recently been beautifully redecorated and furnished. As part of CRL commitment to maintaining property excellence, the entire exterior of River House is currently receiving new siding, flashing and other pro-active improvements at no cost to the new owners.

Welcome to this private cold-de-sac in Colesville, Maryland. This home offers a half-acre lot that is fitting for outdoor activities, social gatherings, and business ventures. Large basement space that extends underneath the garage. Close proximity to I-495 and Maryland Route 200. Recreational buildings and parks are less than miles away. This is suburban living at its best.

OFFER DEADLINE - Offers have been received. Please submit best and final offers by 5/13/26 at 9:00am.Set on 6.32 picturesque acres just north of Elkton, this inviting log home farmette captures the essence of peaceful country living with a distinct equestrian and lifestyle appeal. A blend of open pasture, mature woods and a scenic pond creates a scenic backdrop. While the property’s prime location—just a few miles west of Fair Hill Natural Resource Management Area with renowned equestrian facilities and trails, and only 15 minutes to Newark or Elkton—offers both privacy and everyday convenience.Outdoor living is the true highlight of this property. A screened front porch was added to capture tranquil pond views, while an oversized rear deck overlooks the wooded landscape, offering sweeping views of the surrounding wildlife and natural beauty. Whether relaxing or entertaining, the outdoor spaces are designed to take full advantage of the property’s serene setting.The heart of this log home features an open floor plan with vaulted ceilings, a wood stove, great room, dining area and a recently remodeled kitchen. Completing the main floor are 2 bedrooms, a charming bathroom, and separate laundry room. The upper level area features an en-suite with a fully remodeled bathroom, and a walk-in closet. The sitting area overlooks the great room below.The charming Pond House offers additional space for guests, or as a private office, studio, or gym. This quiet furnished little retreat has living space, an upper sleeping loft, and a covered rear porch directly overlooking the pond.Equestrian and hobby farm buyers will appreciate the existing run-in shed with two stalls, along with open land that could easily be fenced to expand pasture for horses. For those seeking workspace and versatility, the detached 3-car garage is a true highlight—perfect for car enthusiasts and hobbyists alike, featuring workshop space, upper-level storage, and excellent potential for future expansion. An additional shed provides even more storage for equipment and outdoor needs.This is a rare opportunity to experience privacy, nature, and functionality in one beautifully balanced property. Morning coffee, evening sunsets, and quiet moments are all included!

The open house scheduled for 7/2/26 has been canceled.Sellers are Motivated! Welcome to the coveted Villages of Elk Neck, where water-oriented living, privacy, and refined luxury come together. This stunning all-brick-front residence is introduced by beautifully curated gardens and meticulously maintained landscaping, creating an exceptional first impression and striking curb appeal.Inside, soaring vaulted ceilings, a grand staircase, and rich dark hardwood flooring set a sophisticated tone that carries throughout the main level and upper overlook. Just off the foyer, the formal living room offers an elegant space for conversation and relaxation, while the dining room provides a refined setting for gatherings and special occasions. Designed for both everyday living and effortless entertaining, the rear of the home features a seamless connection between the kitchen, dining, and main gathering spaces. The kitchen serves as the heart of the home, showcasing abundant cabinetry, granite countertops, a peninsula with seating, double wall ovens, stainless steel appliances, and the convenience of two pantries. Expansive windows draw in natural light and frame views of the backyard, enhancing the connection to the outdoors. Adjacent to the kitchen, the family room offers a warm and inviting atmosphere anchored by a floor-to-ceiling stone gas fireplace, creating a cozy focal point year-round. A private home office provides an ideal space for remote work or quiet focus, while a well-placed powder room and functional laundry/mudroom with garage access complete the main level with thoughtful practicality. Upstairs, the open design continues with a balcony-style overlook to the family room below. The impressive primary suite serves as a true retreat, featuring a spacious sitting area and an exceptional four walk-in closets. The ensuite bath is designed for relaxation, complete with a glass and tile walk-in shower, dual vanities, and a jetted soaking tub positioned beneath a skylight and beside a large window, filling the space with natural light. Three additional generously sized bedrooms are served by a well-appointed hall bath featuring tile flooring, an updated dual-sink vanity, and a tiled tub/shower combination. The fully finished lower level expands the home’s versatility, offering flexible space suited for recreation, media, fitness, or additional gathering areas, along with a convenient half bath for added comfort. Just off the kitchen, a spacious screened-in porch with skylights extends the living space outdoors, offering a light-filled retreat ideal for morning coffee, dining, or year-round relaxation. Perfectly positioned between the Elk Neck and North East Rivers, this home offers a rare blend of natural beauty and everyday convenience. Minutes from the shops, restaurants, and waterfront amenities of both Elkton and North East, it delivers the ideal balance of peaceful surroundings and easy access to vibrant town life. This is a residence that truly offers it all.

Beautifully Updated Home in a Serene Setting!Welcome to this stunning home filled with thoughtful improvements and timeless charm. The spacious Florida room overlooks a private, beautifully landscaped backyard — your own personal oasis. This room offers unlimited views of the back yard, which was designed in collaboration with a professional landscaper, this garden is a delight in every season and a true haven for butterflies and hummingbirds. You will delight in an outdoor sitting area under a lovely shade tree.The main level features gleaming hardwood floor, a semi-open floor plan with a cozy fireplace perfect for cool evenings, and abundant natural light that creates a calming atmosphere throughout. The large primary suite offers comfort and convenience, and there is the option for a second bedroom on the main level. Current owners have opted to make that room a large office, and it features two closets.The kitchen is a dream — spacious enough for a large island and a generous breakfast area that easily fits a full-sized table. There is a mural border that shows scenes of historic Chestertown. Pantry and plenty of storage. Upstairs, you’ll find two large bedrooms and a full hall bath, ideal for guests or loved ones. Each bedroom offers walk-in storage — no attic ladders needed! Solar operated fans keep the attic spaces cool.Additional highlights include leased solar panels which have been paid out, a large garage with ample storage, additional storage shed with electric and water. , and a fantastic location just minutes from the Chester River and the Chester River Yacht and Country Club. Two zone for heating and cooling.Come see this charming home for yourself — it’s the perfect blend of beauty, comfort, and thoughtful design!

This beautifully maintained custom-built home in the desirable Eagle Manor community combines luxury finishes, thoughtful design, and over an acre of professionally landscaped privacy.Inside, you’ll find an open and airy floor plan featuring 4 bedrooms, 3 full baths, luxury vinyl plank flooring, custom moldings, shiplap accents, two fireplaces, and abundant natural light. The gourmet kitchen is designed for gathering with quartz countertops, a large center island, farmhouse sink, stainless steel appliances, and ample cabinetry.The first-floor primary suite offers a private retreat with a spacious walk-in closet, soaking tub, and walk-in shower. Generous secondary bedrooms and flexible living spaces provide room for guests, a home office, or multigenerational living.Step outside to enjoy your own backyard oasis featuring an oversized screened porch, professionally landscaped grounds, mature privacy plantings, a serene koi pond, irrigation system, and elegant wrought iron fencing. The expansive one-acre lot also offers plenty of room for a future pool.With more than $140,000 in seller improvements, this move-in-ready home offers exceptional quality and value that would be difficult to replicate at today’s construction costs. Conveniently located near Centreville, Chestertown, waterfront marinas, shopping, dining, and the Chesapeake Bay, this is an outstanding opportunity to enjoy the best of Maryland’s Eastern Shore.Schedule your private showing today and experience everything 403 Eagle Manor has to offer.

Rare lakefront opportunity in Kent County offering exceptional privacy and a peaceful natural setting. Tucked away on 2.62 partially wooded acres along Urieville Lake, this beautifully situated property provides a secluded retreat where you can truly unwind and enjoy the outdoors.This spacious 4-bedroom, 3.5-bath home offers flexible living for families and guests alike. The layout includes the option for a first-floor bedroom, three bedrooms on the second level, and an additional bedroom in the finished walk-out basement, providing plenty of room for everyone while maintaining privacy throughout the home.The open-concept main living area is filled with natural light and showcases beautiful views of the surrounding woods and the lake beyond, creating a warm and inviting space for everyday living or entertaining. The home features two full bathrooms on the second floor, a full bath on the lower level, and a convenient half bath on the main floor, all designed with comfort and functionality in mind.The finished walk-out basement adds valuable living space with a bedroom and full bath—ideal for a guest suite, recreation room, home office, or entertainment area—with direct access to the peaceful backyard and lakefront setting.Outside, the property truly shines. The 2.62 acres offer a rare level of privacy, with mature trees and natural surroundings that create a quiet, secluded atmosphere. Whether you're relaxing by the water listening to the geese, gardening, exploring wooded paths, or enjoying lakeside sunsets, this property offers endless opportunities to connect with nature.Situated on Urieville Lake, residents can enjoy fishing, kayaking, and small boating right from their own backyard. The lake spans approximately 35 acres, shaped like the letter “Y,” and supports a healthy fishery including largemouth bass and bluegill, along with occasional catches of pumpkinseed sunfish, brown bullhead catfish, golden shiners, and common carp.If you're searching for a private waterfront escape in Kent County, where nature, space, and tranquility come together, this special property is ready to welcome you home.

This home is the perfect blend of casual elegance and gracious living. It is in meticulous condition and situated on a premium parcel with mature landscaping. A stunning two-story foyer welcomes you into an open floor plan where rooms flow seamlessly across the main level. Quality craftsmanship is evident throughout, highlighted by soaring ceilings, hardwood flooring, and unique architectural details enhanced by abundant natural light.The MAIN LEVEL includes an oversized family room (with adjacent office) which features a propane fireplace plus a wall of windows overlooking the backyard and woods beyond. It adjoins a spacious chef’s kitchen equipped with marble countertops, extensive counter and cabinet space and updated appliances. The centrally located kitchen opens into a vaulted breakfast/sunroom, providing convenient access to the back deck through French doors. It also connects to the formal dining and living rooms. The hall to the garage is conveniently located next to the laundry room and half bath.The UPPER LEVEL includes four spacious bedrooms, ample closets, and two full baths. The spa-like primary suite features a tray ceiling, a large walk-in closet, and an ensuite bath with a double vanity, private water closet, soaking tub, and tile shower.The LOWER LEVEL is huge and is partially finished with a media room and generous storage areas plus roughed-in plumbing for a bathroom. Glass paneled doors lead out to the ground-level patio within the fully fenced backyard. The home is located on the edge of the charming town of Centreville in the desirable community of North Brook, with no HOA in this section.

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James Pearce who held the highest court in the State. The home boasts 6 fireplaces, ornate millwork all over, stained glass windows, soaring ceilings, massive pocket doors, spacious rooms, and surprisingly ample closet space. Homes aren't built like this anymore making adventuring the halls an absolute treat. Water views can be found from various windows of the home with specific angles highlighted seasonally. Outdoor living is celebrated with screened in porch flowing out back from the kitchen, covered front entry porch and second floor covered sleeping porch. The yard itself is a sanctuary with mature azaleas, magnolia, and gingko creating a calming setting. There is a driveway and your car can just stay there because this home is located just blocks walking from all of the dining, shopping, and culture that Chestertown has to offer. This home is part of the Maryland Historic Trust. Own a piece of American history less than two hours from DC, Baltimore, and Philadelphia while enjoying the walkable lifestyle of Chestertown's Historic District.**Interior professional photos are coming soon and are going to be really special**

Welcome to one of Sudlersville's most extraordinary heritage homes, a magnificent Queen Anne Victorian that beautifully honors its historic character while embracing the comforts of modern living. Following an extensive 2019 renovation that left virtually no system untouched, this remarkable residence has been thoughtfully reimagined for today's lifestyle while preserving the timeless architectural details that make it truly one of a kind. Set on more than an acre beneath majestic centuries-old shade trees, this magical family estate commands attention with its soaring turret, five striking bay windows, and deep, sweeping wraparound porch that invites you to slow down and savor every season. Overlooking the neighborhood park, the setting is as enchanting as the home itself, nestled within the quintessential Hallmark town of Sudlersville, where the historic train station now serves as a museum and the soft rumble of the grain train passing through town a few times each week provides a nostalgic reminder of the community's rich heritage. Inside, soaring ceilings, exquisite millwork, and an impressive foyer introduce an unexpectedly open floor plan designed for both gracious entertaining and everyday living. The expansive kitchen is a true gathering place, featuring stunning custom cabinetry that extends to the ceiling with thoughtfully designed pull-out drawers, a dramatic designer backsplash, updated stainless steel appliances, many with transferable warranties, and a large picture window above the sink that fills the space with natural light. The kitchen flows seamlessly into the dining room, beautifully nestled within one of the home's signature bay windows. The adjoining family room creates an airy, connected living space rarely found in historic homes, while multiple rooms open directly onto the wraparound porch, blurring the line between indoor and outdoor living. A dedicated office surrounded by windows offers an inspiring workspace, and the butler's pantry with wet bar provides the perfect staging area for effortless entertaining on the porch and patios. The main-level primary suite offers exceptional convenience with a spacious ensuite bath featuring a soaking tub and separate shower, while a powder room completes the first floor. Upstairs, four additional bedrooms include a private ensuite guest suite and a beautifully appointed hall bath. Fresh new carpeting enhances the upper-level bedrooms, while two of the bedrooms are graced by the home's distinctive bay window bump-outs, creating expansive sitting areas bathed in natural light and showcasing the architectural character that makes this residence so special. A walk-up third floor offers abundant storage along with the enchanting turret room, an unforgettable space ready to become a library, reading retreat, artist's studio, or simply a breathtaking lookout over the surrounding landscape. The immaculate cellar provides exceptional storage, while the park-like grounds are designed for year-round enjoyment with patios, arbors, expansive lawns, a welcoming fire pit tucked beneath towering centuries-old shade trees, and two substantial outbuildings, including a garage and a detached studio currently used as a fitness space. Rich in history yet thoughtfully transformed for thoroughly modern living - including a Level 2 EV Tesla charger! This spectacular Queen Anne Victorian is far more than a home, it is a once-in-a-lifetime opportunity to become the next steward of one of Sudlersville's most treasured residences.

Motivated Sellers, bring all reasonable offers! Beautifully Restored 1890s Victorian in Trappe, MD - 6BR, 3.5BAStunning fully restored 1890s Victorian in the heart of Trappe. This spacious 6-bedroom, 3.5-bath home features a wraparound porch, formal living and dining rooms, a family room, and a marble primary bath. The home offers one gas fireplace for warmth and ambiance, plus four original decorative fireplaces that add timeless character throughout.The modern kitchen includes stainless steel appliances and a 36 gas range.Updated throughout with all-new plumbing and electrical, spray foam insulation, new windows, and a 4-zone heating system. Outdoors, enjoy a large slate patio and generous off-street parking. A rare blend of historic charm and modern efficiency -move-in-ready.Call Today for a Tour!

Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natural light. Two car garage under the house with unfinished basement. Windows, roof, appliances, and HVAC have all been replaced. Electric has been updated. The list of improvements goes on. Come see this for yourself. It's gorgeous!

Welcome to this magnificent 2,042 sq. ft. home nestled on a sprawling 1.72-acre park-like setting, where tranquility meets luxury living. The 20,000-gallon in-ground saltwater pool, complete with maintenance free decking and a liner replaced in the fall of 2022, serves as the centerpiece of outdoor enjoyment. Imagine summer days spent poolside in your personal paradise!Over the past two years, this home has seen numerous upgrades including new ductwork, new lighting, and more. An entire new septic system (2023), and well pressure tank ensure reliability and peace of mind. The attached two-car garage features a new door with epoxy flooring that is both stylish and easy to maintain. Inside, enjoy a refreshed hall bath with a new shower and flooring, fresh paint, and new lighting. New outdoor rear awnings were installed to provide generous shade over the poolside deck areas.Step inside to discover a spacious open floor plan perfect for family gatherings. The large kitchen boasts all-new appliances, a massive island, ample counter space, and plenty of cabinets to make this kitchen a culinary enthusiast’s dream. The inviting living room features a pellet stove fireplace insert, while the adjacent all-season room offers seamless access to the pool and deck area, blending indoor and outdoor living effortlessly.The primary suite is a private sanctuary, complete with a cozy sitting area, a luxurious en-suite bathroom, a generous walk-in closet, and exclusive access to a serene concrete deck by the pool — an ideal spot for a hot tub!In addition to the main house, the property includes a two-story detached garage with electric and water access, perfect for a workshop or lounge area. It even has its own separate driveway, perfect spot for an RV, and a boat. The upper level has plenty of room for additional storage. Two additional sheds provide convenient storage for lawn and pool equipment.This exceptional property backs onto a wonderfully wooded area, enhancing your privacy. With plenty of room for future additions like a pole barn, the possibilities are endless.The property is conveniently located off Route 1 for easy commuting, minutes from Bayhealth hospital, and only 23 miles from Rehobeth Beach! Do not miss the opportunity to own this stunning home, designed for both relaxation and entertaining. Schedule your private tour today and experience the perfect blend of modern upgrades and natural beauty!

This stunning Colonial is the one everyone waits for—and it does NOT disappoint. Offering 3 bedrooms and 2.5 baths, this beautifully maintained home is filled with upgrades and thoughtful details throughout.The updated kitchen features Amish-made cabinetry, quartz countertops, hardwood flooring, and plenty of space for cooking and gathering. The home offers two gas fireplaces and an extended family room addition, creating a warm and inviting atmosphere perfect for everyday living and entertaining. A built-in coffee/bar area adds even more charm and functionality. A versatile first-floor office/playroom provides the perfect flex space for working from home, a play area, or additional living space.Upstairs, the spacious primary suite includes a soaking tub, double sink vanity, and a separate shower, while the additional full bath has been tastefully updated. Major improvements include new windows, a newer roof, solar panels, and an updated HVAC system (2023), offering both comfort and efficiency.Situated on just over an acre, the outdoor space is truly exceptional. The property backs to farmland, providing peaceful views and added privacy. Enjoy the beautifully maintained yard, in-ground pool, composite deck, and outdoor cabana—perfect for relaxing or entertaining all season long.Additional features include a full basement with poured concrete walls, a Bilco door exit, and endless potential for finishing to your needs, along with a 2-car garage.Located in the Bohemia Manor School District, homes like this—with this setting, space, and level of care—do not come along often.

Experience refined living at 156 Sunnybrook Drive in Elkton, Maryland. This beautifully appointed Colonial offers 2800+- sq. ft. of exceptional living space on a private 1.13-acre corner lot in the desirable Bohemia Manor School District. Step inside to an inviting open layout where the kitchen features granite counters, stainless steel appliances, and a charming breakfast nook that flows effortlessly into the warm and welcoming family room. With 3 spacious bedrooms, 2.5 baths, and main-level laundry, this home is designed for both comfort and convenience. The primary suite offers a serene retreat with a bathroom featuring a soaking tub and separate shower. The finished lower level provides an extended living area complete with a woodstove, new carpet and paint, bilco outdoor access, and ample storage. Thoughtful upgrades such as a Rinnai on-demand water heater, Rain Soft water system, 2-car garage, owned solar panels, and a 50-year architectural roof elevate the home’s quality and efficiency. Outdoors, the property truly shines. Enjoy a resort-style setting featuring a fenced rear yard, low-maintenance deck with PVC railings, and a sparkling inground pool with a 2022 liner—perfect for elegant summer entertaining. The impressive 32x24 pole barn with electric offers endless possibilities for hobbies, storage, or workspace. All of this is complemented by an ideal location just minutes from waterfront dining, boutique shops, and the charm of Historic Chesapeake City. With no HOA, this property combines luxury, privacy, and convenience in one exceptional offering.

Spacious Townhome with Golf Course Views and just 1,000 feet walk to Bay Hills golf clubhouse.Property OverviewThis large townhome overlooks the 17th golf hole at Bay Hills Golf Club, offering impressive views of the course. The home features four spacious bedrooms and three and a half bathrooms, providing ample space for family and guests.Outdoor and Entertaining SpacesEnjoy entertaining or simply relaxing on the oversized deck, which offers beautiful views of the 17th fairway. The deck is ideal for gatherings, outdoor dining, or enjoying peaceful evenings surrounded by the natural beauty of the golf course.Interior FeaturesThe main level boasts bright and open living spaces, creating a welcoming atmosphere. The finished lower level includes a fourth bedroom that may also serve as a family room. This space features a full bath and provides convenient walkout access to the outdoors.Recent UpdatesRecent improvements make this home move-in ready, including brand new flooring, new carpet, and fresh paint throughout. Additionally, a new roof was installed just six months ago, ensuring durability and peace of mind.Community Amenities and LocationLocated in the desirable Bay Hills community, residents enjoy access to amenities such as golf, a pool, tennis courts, and a clubhouse. The property is conveniently close to Annapolis, Severna Park, shopping, dining, and major commuter routes.

Don't miss this rare opportunity to own one of the only waterfront lots still available on the Chester River! Perfectly positioned just across the river from the historic charm of Chestertown, this premier property offers front-row access to the area's beloved events, including the Tea Party Festival, Fourth of July celebrations, and the Dickens Festival.Situated in a highly desirable and tranquil location, this lot has been lined with California privet bush and mostly cleared to reveal unobstructed views of the Chester River. The invasive phragmites is scheduled to be sprayed soon! Enjoy direct water access with the potential to add a dock and access deep water off the shore. Imagine your custom-built dream home or weekend escape!This is a once-in-a-lifetime chance to build your ideal waterfront retreat in one of Maryland’s most scenic and culturally rich areas. Call to schedule your private showing today!

Welcome home to this pristine, energy-efficient Colonial that effortlessly blends modern luxury with incredible cost-saving sustainability. If you are looking for a home that checks every single box on your wish list, this 4 to 5 bedroom, 2.5 bath masterpiece is the one you’ve been waiting for!From the moment you step inside, gleaming hardwood floors guide you through a bright, thoughtful layout. The sun-drenched front office is perfect for remote work, while the formal living and dining rooms feature elegant crown molding made for hosting. Nearby, the upgraded gourmet kitchen steals the show with gorgeous quartz countertops, a gas stove, stainless steel appliances and a cozy breakfast view into the family room, where a warm gas fireplace awaits. You’ll also love the main-floor laundry room, tucked behind a trendy barn door right off the spacious 2-car garage.Upstairs, the luxury continues with beautiful hardwoods throughout all the bedrooms. The primary suite is a true private retreat, boasting two closets and an upgraded ensuite bath featuring double vanities and an extra-large, custom walk-in tiled shower. Three more generously sized bedrooms offer plenty of space, including a massive bonus room that easily serves as a fifth bedroom or second office. There is even a huge walk-in closet that can easily be converted back into a second-floor laundry room if you prefer!Your summers just got a major upgrade with a backyard built for staycations. Unwind on the massive 20x20 screened porch, or cool off in the crystal-clear, custom concrete inground pool, complete with a soothing waterfall feature, a high-efficiency heater, and a self-cleaning system. After a long day, soak in your private hot tub or tend to the raised garden bed. The beautifully fenced yard also features a custom, professionally leveled Amish-built Penn Dutch shed for all your storage needs.The best part? You can say goodbye to high utility bills. This home is engineered for maximum savings with a massive 9 kW solar panel system, energy-efficient 2x6 walls with R19 insulation, a high-efficiency heat pump, and a natural gas heating system.With an unfinished basement ready for your personal touch, a freshly sealed driveway, and professional lawn treatments already paid for through the rest of 2026, this home is entirely turn-key and ready for its next chapter.

Stunning waterfront property with private dock site on the Chester River. The house has been gutted and needs a complete rehab, or it can be removed and rebuilt to suit your dreams. Building plans are available. The property features a brand-new BAT septic system that has yet to be connected. Beautiful location and views! Just a short drive to Chestertown. 3 ft mean low water, buyer to verify.

Welcome to 408 Laurens Way, located at the end of a quiet cul-de-sac in the heart of Queen Anne’s County. This beautifully maintained home offers nearly an acre of privacy, backing to open agricultural land. With approximately 2,400 square feet of living space, the property includes 3 bedrooms, 2.5 bathrooms, a spacious family room with a fireplace, a formal dining room, and an additional flex room that can serve as an office or den.Since purchasing, the sellers have made extensive updates, including a new roof, new HVAC system, fresh insulation and vapor barrier, new carpeting in all bedrooms, updated appliances, fresh interior paint, and more.The exterior features a thoughtfully designed hardscape, outbuildings, chicken coops, and plenty of outdoor space for recreation or gardening. The attached garage provides overhead attic storage with easy access.Experience the tranquility of Maryland’s Eastern Shore in this meticulously cared-for property, ready to welcome its next owner.

Stunning Waterfront Home on the Elk River in Locust Point! Welcome to 55 River Road, Elkton, MD 21921, offering beautiful Elk River views and approximately 2,200± sq. ft. of total living space. This 3-bedroom, 3 full bathroom home features an open floor plan with immediate water views upon entry. Interior highlights include crown molding, plantation shutters, luxury LVP flooring, and fresh paint throughout (currently in progress).The eat-in kitchen is complete with granite countertops, dining area, and all appliances included. Enjoy water views from the spacious living room with a sliding door leading to a newer composite deck and paver patio, ideal for outdoor entertaining.The primary bedroom offers an en-suite bath with tiled walk-in shower and custom shelving. The finished lower level includes a side entrance and provides flexible space for a home office, family room, or additional living area.Recent updates include a new Architectural Lifetime roof (2024), Gutters/Downspouts (2024) new propane HVAC system (2024), and new bulkhead (2021). Conveniently located near multiple marinas and a community boat ramp.

Originally built in 1930. Completely updated and tastefully renovated. Perfect year round or seasonal cottage. In the very special private community of Kenmtore Park. Year round activities for all. Nightly get together at the Big Pier to capture the most beautiful sunsets on the Sassafras River. Morning coffee is served on the deck off of the kitchen. Invite friends over for a day at the beach then a casual dinner served on the secluded patio off the entertainment room. Great place also for a fire pit in the cooler months. All bedrooms are on the opposite side of the home from the entertainment room and the patio for convenient privacy. Walk to the beach or ride down on a golf car, there is always something to watch and usually someone to talk with. Kentmore is close to Galena on the North side. Visit the enchanting Cross Street Market and the Sassy market. Get take out from Twinnys or Galena Pizza. Upscale dining at the Kitty Knight or the Fish Whistle. Head South from Kentmore and come across Washington College and all the amenities of Historic Chestertown. Jump on your boat or hitch a ride on a neighbor's boat for a great day on the river. Boating, wakeboarding, skiing or tubing. Jet ski anyone? At night view the endless unobstructed sky and a million stars, planets, and the moon.

Spacious and beautifully updated 4 bedroom, 3.5 bath home with a finished walkout lower level offering exceptional flexibility for multi-generational living or guest space. The lower level features a complete in-law suite with a possible 5th bedroom, living room with slider leading to walk-up stairs, full kitchen, and full bathroom with private access possibilities.The main level offers a gorgeous new white kitchen with granite countertops, updated flooring, cozy gas fireplace, 9-foot ceilings, and an open layout ideal for everyday living and entertaining. Enjoy the 18x16 composite deck off the breakfast room with a 6-foot sliding door overlooking the fenced rear yard.Additional features include a brick front exterior, dual-zoned HVAC systems, Rain Soft water conditioning system, battery backup sump pump, walkout lower level, quick EV charging setup for two electric vehicles, and solar panels for added efficiency and savings with monthly credit.This home offers space, versatility, and upgrades throughout with endless possibilities for today’s lifestyle needs.Conveniently located with easy access to I-95, this home offers an ideal commute — just 35 minutes to Wilmington and only 20 minutes to Newark, making it perfect for commuters looking to enjoy a more peaceful setting without sacrificing accessibility.

Seller says sell! Massive price reduction ! Below market for this pristine home well situated in chestertown historic district!A rare Water Street opportunity—see your boat from the front porch and enjoy walkable waterfront living in Chestertown. This thoughtfully rebuilt historic home offers 4 bedrooms, 3.5 baths, flexible guest spaces, and a water-view deck built to support a hot tub. Perfect as a primary residence or low-maintenance Chesapeake pied-à-terre for DC, Baltimore, and Philadelphia weekenders. Quality finishes include Andersen composite windows with plantation shutters, Heartland appliances, handcrafted cabinetry, and excellent storage. Walk to parks, dining, shops, arts, and the harbor.Vacant lot next door is separately owned.

Welcome to 14504 John Peel Road, located in a desirable waterfront-oriented community in Galena offering private community dock access and the opportunity to enjoy the Eastern Shore lifestyle. Conveniently located just minutes from Route 301, this spacious 4-bedroom, 2.5-bath Colonial offers over 2,300 square feet of comfortable living space with plenty of room for everyone.The main level features a beautiful kitchen with cherry cabinetry and lvp flooring, a dining area or family room with an electric fireplace, and a convenient half bath. Enjoy additional living space in the screened-in porch, perfect for relaxing and taking in the peaceful surroundings. The front of the home offers two formal living rooms, providing flexible space for entertaining, a home office, or additional gathering areas.Upstairs you’ll find all four bedrooms and two full bathrooms, including a spacious primary suite with a Juliet balcony. The basement offers even more possibilities with a wood stove and additional space for storage, hobbies, or recreation. An attached two-car garage adds everyday convenience.

Welcome to this beautifully updated 4-bedroom, 3-full-bath home situated on a private 1.14-acre lot in a wonderful Middletown community within the sought-after Appoquinimink School District. Offering a rare combination of space, updates, privacy, and location, this home is truly one of a kind.The interior has been thoughtfully refreshed with brand-new carpet, all-new paint, new light fixtures, and an upgraded kitchen featuring quartz countertops. The main level includes a first-floor bedroom and full bathroom, making it ideal for guests, multigenerational living, or added everyday convenience. A spacious dining room and large front office/living room provide flexible spaces for entertaining, working from home, or relaxing.The family room features a beautiful stone fireplace and opens seamlessly to the kitchen and eat-in dining area, creating a warm and inviting central gathering space. The kitchen offers stylish updates, great functionality, and an easy flow for both daily living and entertaining.Outside, enjoy a private, tree-lined, fenced backyard with a creek behind the property, offering a peaceful and scenic setting that is hard to find. The yard extends beyond the fence and there's even a walking path to a creek! New septic is being installed June 2026. The home also features new siding on the front exterior, adding to its fresh curb appeal.With 4 bedrooms, 3 full bathrooms, updated finishes, a flexible floor plan, 1.14 acres, and a private yard in Appoquinimink schools, this Middletown home offers an exceptional opportunity in a truly special setting. Schedule today to see this very special, fully updated and move-in-ready, home!

Welcome to 9816 Fairlee Road. Be Sure to Click the Virtual Tour!! This property has been meticulously cared for by the current owners and it shows. The property sits on 6.29 acres! If you want plenty of land without giving up on high end fixtures, this is the home for you. Pride of ownership shines through in this gem of a home. The paved driveway leads to a parking pad and a beautiful piece of property. This rancher gives you plenty of space both inside and out. Recently, there was an addition of a mudroom and a second owners suite. Both owners suites have their own bathroom and walk-in shower and one even has a jetted Jacuzzi tub to help you unwind after a long day. There is upgraded flooring through-out, whether it be hardwood or tile, every room feels polished and upscale. The living room includes a woodstove that was installed in 2025 along with a new chimney pipe. There is a creek directly behind your property, which means, water is just a short stroll away. Enjoy tons of natural light in the spacious kitchen where quartz countertops are partnered with a Stainless Steel Refrigerator, built-in microwave and stove. Soft-close cabinets and drawers add to the upscale feel. This home has three spacious bedrooms and three full baths. The un-finished lower level provides you with even more space for storage or it can be your very own blank canvas to finish and increase your living space. The laundry area is in the basement and the washer and dryer will stay with the home. The sliding glass door in the kitchen allows access to your deck and backyard. Enjoy the peace and quiet. Don't be surprised if you see ducks, turkey or deer, they have been known to enjoy the 6+ acres too! The water treatment system has been thoroughly maintained and will convey with the home. High Speed Talkie internet is available. New windows installed throughout most of the home in 2020. This is an Amazing Home! It is turn-key and ready to Welcome its New Owners.

Welcome to one of Easton’s more desirable communities—where space, comfort, and timeless style come together in this elegant 5,100+ sq ft home. With 3,322 sq ft on the main and upper level plus a full 1,792 sq ft unfinished basement, this property offers an abundance of living space and endless potential.Inside, you’ll find a gracious floor plan designed for both everyday living and entertaining. The main level features a formal living room, formal dining room, a spacious family room with a fireplace, and a private office that can easily serve as a 4th bedroom. The kitchen and gathering areas flow seamlessly, creating a welcoming setting for hosting or relaxing. Upstairs, the home offers 3 generous bedrooms and 2 full baths, including a comfortable primary suite with ample closet space.Additional highlights include a 2-car garage, 2.5 baths, and thoughtful architectural details throughout. The expansive unfinished basement provides opportunities for future customization—whether a recreation room, fitness area, or workshop.Located in the sought-after Easton community, this home combines quiet residential living with close proximity to Easton’s shops, dining, schools, and medical facilities. If you’ve been searching for space, convenience, and the chance to make a home truly your own—this is it.

If you are looking for a beautifully designed Victorian home in a quaint waterfront small town with a marina, this is the one for you! This turn-key historical home has been thoughtfully designed with an Airbnb or vacation home use in mind, complete with custom decor and carefully selected antiques, to instantly transport you into another world. Only steps from the small town of Chesapeake City along the famous C&D Canal, you can enjoy the many town events, shops, cafe, waterfront restaurant, ice cream shop, marina, and more! This home has been carefully renovated to make it shine and have modern conveniences while maintaining its Victorian charm. The wrap-around front porch welcomes you to the home and features a plaque naming this the Barwick House circa 1850. Walking into the front door, you are greeted by the lovely foyer with a vestibule seating area. To the left of this is a living room with electric fireplace and beautiful mantle. The dining room has been opened to the kitchen which makes it a welcoming space to entertain. This room is a showpiece with exposed ceiling, dual chandeliers, large dining table, custom island and cabinetry utilizing antique furniture to take the charm to the next level! Off the kitchen is a laundry room, mudroom, and a sunroom which could also be used as a first floor bedroom or bonus room. There is also full bathroom with ADA walk-in shower and intricate detailing in the design with nods to the Maryland waterfront setting. The second floor has one of the best features of the house: the first bedroom not only has beautiful exposed beams, but it also features custom stairs up to a secret loft, perfect for a kids hide-out or reading nook, with railing hand-wrapped with nautical rope to create a magical getaway experience! This second floor has two more bedrooms, one with exposed beams & loft-style decor ledge and the other with double closets and built-in shelves, and the second full bathroom with clawfoot tub. The third floor has two bedrooms, one which has a beautiful feaux-fireplace mantle. There are 5 bedrooms total in this home, plus the bonus room/sunroom on the first floor, and 2 full bathrooms. Outside, you'll find a large deck to enjoy all summer long, as well as a spacious back yard - only a few blocks from the Marina! This property has convenient off-street parking for up to 6 cars in the back and there is permitted parking along the street. The mechanicals have also been updated for buyer's peace of mind, including New Roof 2023, New Electrical & Panels 2022-2023, New Wall Mini-Split Heating/Cooling 2022, added insulation, and much more! This is a one-of-a-kind gem that you will not want to miss!

There’s no place like home! Welcome to the Flyway neighborhood in Chestertown, where this 4 bedroom, 3.5 bath home offers a flexible layout with both formal and casual living spaces. The front entry opens to a formal dining room and a separate bonus room that can serve as a living room, playroom, or home office. The family room with propane fireplace flows into the eat-in kitchen that features a breakfast bar, pantry, and space for a table. Just off the kitchen is a half bathroom and interior access to the 2 car garage. Sliding glass doors lead to a composite deck with steps down to the spacious fenced backyard, all situated on a 1 acre lot offering space to enjoy outdoor living. Upstairs is the primary suite with two walk-in closets and a private bath with dual vanity and walk-in shower. A secondary suite includes its own private bath and walk-in closet, while two additional bedrooms share a hall bath. Laundry is conveniently located on the upper level. Recent updates include a new roof on the home and shed (2025) and recently replaced water heaters (downstairs in 2025, upstairs in 2019). Conveniently located just minutes from downtown Chestertown’s shops, restaurants, waterfront, and Washington College. Schedule your showing today!

Welcome HOME! This beautifully updated 4 Bedroom, 3 Full Bath Rancher with screened in porch, has been meticulously renovated over the past 4 years, nearly every detail has been refreshed!!Kitchen has been updated with freshly painted cabinetry, granite countertop with new sink, a trendy tile backsplash, and modern appliances, creating a clean, updated look. Bright and functional, this space blends style with everyday convenience, making it the heart of the home.Hardwood flooring has been replaced, the entire house has a fresh coat of neutral paint, new roof (2021), owned solar panels, Thompson Creek windows (2023) and sliders, washer/dryer, fridge, microwave, garage door, interior garage upgrades (flooring, panels), pellet stove, lighting, ceiling fans, and much more.The lower level offers 12ft high ceilings, a walk-out slider to the back yard, bedroom with full bath, large walk-in closet, and plenty of space for entertaining or potential in-law/apartment use. Large accessible storage area with plenty of shelving. Landscaping has been completely redone, giving the home a fresh, like-new feel.This stunning home is located just a few minutes from downtown North East!

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District. Located on a quiet side street just a block from Chestertown's dining, shopping, and galleries, this is the perfect blend of social and tranquil. This means that walking down to Evergrain or Modern Stone Age Kitchen for a croissant and cappuccino before a morning stroll along the waterfront promenade could become part of your morning routine. The thoughtful updates over the years have opened the floor plan and allowed for a modern layout. Many serious upgrades have occurred in the past year including the kitchen and electrical service. The wood burning stove, basement for storage, and garden building are amazing benefits. Invest wisely in an amazing home while improving your quality of life in this incredible community on the water less than 2 hours from Washington DC, Philadelphia, and Baltimore.

Fresh updates, generous living space, and a location that makes everyday living easier — welcome to 235 Green Street in Centreville! With brand-new carpet just installed and a fresh new feel throughout, this 4-bedroom, 3.5-bath Colonial offers over 2,600 sqft of flexible living space at an exceptional new price.The main level features multiple gathering spaces including a spacious family room with wood-burning fireplace, a bright morning room off the kitchen overlooking the backyard, and an additional front living area that can easily function as a sitting room, home office, formal dining space, or play area depending on your needs. The centrally located kitchen offers 42” white cabinetry, sparkling black quartz countertops, and seamless flow into the surrounding living spaces. Upstairs, generously sized bedrooms provide room to spread out, while the partially finished basement with full bath offers additional flexible space for a recreation room, home gym, playroom, guest setup, or future expansion possibilities.Outside, enjoy the covered rear deck overlooking the flat backyard with privacy trees and storage shed — perfect for relaxing or entertaining during the upcoming summer months.What truly sets this home apart is its location — just moments from the YMCA, grocery shopping, downtown Centreville restaurants, local shops, parks, and everyday conveniences. Whether it’s grabbing dinner, heading to a workout class, or enjoying community events downtown, this home blends space, comfort, and a walkable lifestyle that’s hard to find at this price point.Additional highlights include a newer roof, 2-car garage, and convenient access to Route 301 & Rt 213 for an easy commute.A rare opportunity to own a move-in ready home with space to grow in one of Centreville’s most convenient locations. Be sure to check out the 3D iGuide Tour!

Welcome to your future home, a stunning residence nestled on a sprawling 1.5-acre lot, offering the perfect balance of comfort, privacy, and space. This impressive property boasts 5 generously sized bedrooms, each providing a peaceful retreat for family members or guests. With 3 full bathrooms, mornings and evenings are sure to run smoothly for everyone in the household. Step inside to discover a bright and open floor plan featuring inviting living areas filled with natural light. The large, modern kitchen was fully remodeled in 2022 with stainless steel appliances, white cabinetry, and handpicked quartz countertops, making it ideal for both everyday meals and entertaining. The dining area flows seamlessly into the spacious family room, where you can relax by the pellet stove or enjoy gatherings with loved ones.Outside, the expansive 1.5-acre grounds offer countless possibilities & was fully fenced in 2024 for an added piece of mind. Plenty of room for outdoor gatherings on the deck and space to play in the yard! The property also provides ample parking with a 3-car garage and an extended driveway. Recent updates include Pella windows throughout (2023) New carpet (2024) Downstairs bathroom remodeled (2023) Roof (2018) with a 50-year transferable warranty. Don’t miss the opportunity to make this remarkable property your own place where you can enjoy space, comfort, and the freedom to create your ideal lifestyle.

2024 new-construction coastal townhome in the highly sought-after Sea Oaks Village in Berlin, MD! Boasting an expansive, rare 2,684 sq ft Easton layout by Lennar, this meticulously maintained 3BR, 3.5BA residence perfectly balances modern upgrades with coastal convenience.The open-concept main level features durable LVP flooring, recessed lighting, and a gourmet chef’s kitchen with a massive quartz island, walk-in pantry, and a dedicated wet bar. Designed for indoor-outdoor living, this premium unit directly overlooks the pristine community pool. Enjoy the view from two private levels: a 2nd-floor composite deck and a 3rd-floor balcony off the massive upper loft—perfect for a home office or media room.Low HOA fees cover lawn care, trash, and top-tier amenities: pool, playground, pickleball, and basketball courts. Parking includes an attached 2-car garage + 2-car driveway. Located in West Ocean City, you are just 10-11 minutes from Assateague Island and the Ocean City Boardwalk.

From the moment you arrive, this charming Cape Cod feels like home. Built in 2002 with 2x6 construction and beautifully updated in 2021, it offers the perfect mix of comfortable living and thoughtful upgrades.Inside, you’ll find 4 spacious bedrooms and 3.5 baths, 9' ceilings, along with a warm, welcoming interior featuring hardwood floors, recessed lighting, and touches of stained glass that add just the right amount of character. The kitchen truly is the heart of the home, with upgraded countertops, stainless steel appliances, and a center island that’s perfect for everything from quick breakfasts to gathering with friends and family.The living room invites you to slow down and relax, centered around a beautiful marble fireplace that makes chilly evenings feel extra cozy. You’ll also appreciate the convenience of main-level laundry, plus an additional hookup in the basement.Downstairs, the partially finished basement creates a fun and flexible space to enjoy—complete with a home theater, a fully stocked bar with seating, a full bathroom, and plenty of room left for storage.Set on 0.65 acres and backing to trees, the outdoor space offers a peaceful, private setting. Whether you're enjoying your morning coffee on the deck or winding down at the end of the day, it’s easy to feel at home here. The outbuilding and shed provide plenty of extra space for hobbies, tools, or storage.With an attached garage and plenty of driveway parking, this home checks all the boxes for comfort, space, and everyday ease. Seller's home warranty is good through September and is transferrable.If you’ve been looking for a home that feels inviting the moment you walk in, you won’t want to miss this one.

*BRAND NEW WATERPROOF FLOORING JUST INSTALLED*MOTIVATED SELLER, BRING OFFERS!Tucked away on a quiet cul‑de‑sac in the highly desirable Rivers End community, this spacious home offers the perfect blend of comfort, functionality, and coastal charm. Residents enjoy a welcoming neighborhood atmosphere with a community fishing pond, recreational areas, neighborhood events, and golf‑cart‑friendly streets—all just minutes from the hustle and bustle of Seaford and a short drive to the beaches.Designed for both everyday living and entertaining, the open‑concept layout features a large living room that flows seamlessly into the kitchen, creating a bright and inviting gathering space with a propane hookup already in place. The kitchen is thoughtfully appointed with tile backsplash, under‑cabinet lighting, a built‑in computer desk, and updated appliances, including a newer dishwasher (2025) and refrigerator (2024).A separate dining room with vaulted ceilings adds elegance, while hardwood interior doors and vaulted bedroom ceilings with French‑door closets bring character throughout the home. The oversized primary suite is a true retreat, featuring double‑door entry, a large walk‑in closet, luxury vinyl plank flooring, a jetted soaking tub, and a separate stall shower.The second‑floor bonus room has been converted into an additional bedroom with a sitting or play area, maximizing flexibility, while another bedroom includes a private half bath—ideal for guests or multi‑generational living. The home offers four/five bedrooms (septic approved for three).Additional highlights include a spacious laundry room that doubles as a pantry with built‑in storage, new smoke detectors, and a crawl space with a plastic vapor barrier. Major systems have been carefully maintained, including a Trane HVAC system (2020) as one out of the two in place (dual zoned) and a hot water heater approximately five years old.The oversized, fully drywalled garage provides ample space for storage, hobbies, or equipment and includes a generator outlet already installed. Outside, enjoy a private backyard with irrigation—perfect for relaxing or entertaining in a peaceful cul‑de‑sac setting.Spend your weekends fishing or small boating in the community pond, dining at local seafood restaurants, or enjoying easy access to nearby beaches for day trips. This home delivers space, convenience, and a vibrant community lifestyle—an exceptional opportunity for coastal living.A flooring credit is offered and can be applied at settlement. Sale is contingent upon the seller’s successful settlement on another home currently under contract. Take advantage of an opportunity to be in this neighborhood at the lowest price you will ever see in River's End! Instant equity, priced to let go now!

Get your mahjong on in this Vibrant and Active 55+ Community. Plenty of activities to maintain your active lifestyle that include a Community Clubhouse with exercise rooms, craft rooms, outdoor pool, tennis and pickleball courts, just to name a few. This pristine one level living Claiborne Model has been meticulously maintained and extensively updated to be move-in ready with new stainless steel appliances that includes a gas stove, a 3 yr old roof, new HVAC, shutters, updated bathrooms including a glass walk-in shower, built-ins in your primary closet, paver patio, and fresh paint throughout. Underground irrigation system keeps your garden beds fresh with low maintenance, and will get you on the cover of Better Homes and Garden in no time. Close to the quaint downtown Easton area and all of its amenities.

Welcome to 25428 Worton Lynch Road in Worton, Maryland! Situated on 1.28 acres, this charming 3-bedroom, 2.5-bath home offers comfortable living with thoughtful features throughout.The heart of the home is the kitchen, featuring granite countertops, LVP flooring, and ample cabinet space for cooking and entertaining. Just off the kitchen, the inviting living room boasts beautiful hardwood floors, a shiplap accent wall, and an electric fireplace that creates a warm and welcoming atmosphere. A convenient half bath is also located on the first floor for guests.The spacious first-floor primary suite provides a private retreat with a large walk-in closet, a hidden closet for additional storage, and an ensuite bathroom complete with a tiled shower. Upstairs, you'll find two additional bedrooms with carpeting and a full bathroom, offering comfortable space for family or guests.A full basement with a wood stove adds valuable storage, workshop potential, or future finishing possibilities. Outside, enjoy the peaceful setting from the rear deck overlooking the 1.28-acre property. Additional features include a shed with a concrete pad and a swing set that conveys with the sale.Offering the perfect blend of comfort, space, and country charm, this Worton property is ready to welcome its next owners home.

Spacious & Updated Home in Cloverfields on Kent IslandWelcome to this beautifully improved home located in the desirable Cloverfields community on Kent Island in Stevensville. Set on an oversized double lot with a private, tree-lined backyard with a brand-new privacy fence, this 3 bedroom, 2 bath home offers over 2,300 sq ft of total living space and a long list of recent upgrades.On the upper level, enjoy an open concept with laminate flooring throughout. An open kitchen with breakfast bar has all the appliances you need including dishwasher (one year old), stove (less than two years old) and a brand-new microwave. The dining room walks out to a screened in balcony to enjoy your morning coffee while catching the morning news or Today show. The living room features a large bay window allowing lots of natural light.The newly renovated primary suite features brand new luxury plank flooring, walk-in closet and beautifully renovated primary bath with soaking tub, double sinks and walk in shower. A second bedroom and second full bath round out the upper level rooms.On the lower level you'll find a generously sized third bedroom, large family room with fireplace that walks out to the fenced in yard, laundry area and workshop with access out to the driveway area. Rough in plumbing appears to be in place for an additional bathroom but buyers are responsible for their own due diligence to add 3rd bath.Major improvements include a new HVAC system, privacy fencing, and new siding and roof just completed at the end of October 2025.Cloverfields offers exceptional amenities: private beach on the Chester River, marina with boat ramp and rental slips, seasonal pool, playground, clubhouse, and low annual HOA fees. Conveniently located just minutes from the Chesapeake Bay Bridge, with easy access to Annapolis, Baltimore, and D.C.Owners are motivated— purchased in 2024 with plans to make this their dream home, a job transfer has prompted a quick sale. Don’t miss this opportunity to own in one of Kent Island’s most sought-after communities.

Nestled in the award-winning Symphony Village Active Adult 55+ community, this well-maintained contemporary home offers the perfect size for living, entertaining, and relaxing, featuring 2 bedrooms, 2 full baths, and a versatile den/office. Thoughtfully designed spaces and an exceptional array of amenities make this home both comfortable and functional.Recent updates include fresh interior paint and new carpet in the bedrooms, reflecting the care and attention given to the property. A spacious three-season sunroom with Eze-Breeze windows extends the living space, creating the perfect setting to relax and enjoy the changing seasons in comfort.Outdoor living continues with a beautifully designed paver patio, ideal for entertaining, dining, or simply enjoying the peaceful surroundings. The home also features a sky basement over the garage, providing valuable additional storage or flexible space to accommodate a variety of needs.Residents enjoy access to scenic walking trails, indoor and outdoor pools, fitness center, clubhouse, game room, tennis courts, pickleball, bocce, putting green, picnic areas, and a variety of community activities.Ideally located just minutes from downtown Centreville, you’ll enjoy nearby restaurants, the bay for boating and waterfront picnics, and easy access to Chestertown, Easton, and Annapolis. Maryland and Delaware beaches are also within convenient driving distance.

Spacious 4-bedroom, 2 full and 1 half bath home located in desirable Preston, MD. This property offers the perfect blend of comfort and functionality, featuring a 3-car heated garage, central air, and a heat pump for year-round efficiency. Enjoy outdoor living with a deck complete with awning, a large yard supported by an underground irrigation system, and an additional shed for storage. Inside, relax in the bright sunroom or cozy up by the gas fireplace. A full-house generator provides added peace of mind. Situated in a great location with plenty of space to spread out—this home truly has it all!

Nestled on just over 2 acres in Trappe, this spacious 3-bedroom, 2-bath home offers nearly 2,500 square feet of living space with room to grow, gather, and make lasting memories. Inside, you'll find a large eat-in kitchen with center island and abundant wine storage, separate dining room, family room, and living room—providing plenty of space for everyday life, holiday celebrations, and everything in between. The expansive sunroom is sure to become a favorite gathering spot, while the oversized primary suite offers two closets and a unique ensuite bath featuring two showers. A fully floored attic provides exceptional storage and includes a bonus room perfect for a playroom, gaming room, hobby space, or quiet retreat. The previous owner had planned to add direct access from the garage, creating even more potential for this unique space. The walk-out basement with exterior access offers endless possibilities for a workshop, recreation room, home gym, or additional storage. Outside, two spacious decks overlook the property, offering plenty of room for entertaining, backyard adventures, gardening, and enjoying the peaceful Eastern Shore setting. Estate sale. Property sold As-Is

Nestled in the serene Easton Club East/Chesapeake by Del Webb community, this exquisite 3-bedroom, 2.5-bathroom residence is designed for those seeking a refined lifestyle. With a minimum age requirement of 55, this vibrant community offers a perfect blend of comfort and luxury. Step inside to discover a spacious 3,052 sq. ft. layout adorned with elegant crown moldings and wood flooring. The gourmet kitchen, featuring upgraded countertops and stainless steel appliances, invites culinary creativity, while the cozy family room with gas fireplace off the kitchen provides a warm gathering space. Enjoy the convenience of a main-floor laundry and a primary suite complete with bath and walk-in closet. The exterior boasts charming brick and vinyl siding, complemented by an underground lawn sprinkler system. Relax on your private patio or take a leisurely stroll along the community's scenic jog/walk paths. 55+ age-restricted section. The community amenities feature Clubhouse, exercise rooms, ballroom, meeting rooms, library, card and craft rooms, outdoor pool, tennis and pickleball courts, bocce ball, horse shoes, exercise paths, picnic areas and putting green, perfect for socializing or unwinding. With an attached rear-entry garage and a concrete driveway, convenience is at your fingertips. Experience the exclusive lifestyle that awaits in this remarkable home, where every detail has been thoughtfully curated for your comfort and enjoyment. PRIME LOCATION, just minutes to downtown Easton shopping, restaurants, churches and medical facilities. Only 30 minutes to the Bay Bridge, 1.5 hours to Maryland/Delaware beaches and within 1-1.5 hours to Annapolis, Baltimore, Washington DC and international airports.

HOME IS STILL AVAILABLE TO SEE AND MAKE OFFERS!!! 72 Hour Kick Out Clause in Effect.Tucked away in the peaceful countryside on the Queen Anne’s County side of Chestertown, this charming one-level rancher offers the space, comfort, and tranquility you’ve been waiting for.Situated on a full acre and boasting over 2,000 sq. ft. of living space, this home is designed for easy, one-level living with room to truly spread out. Offering 3 large bedrooms and 2.5 bathrooms, plus the added convenience of two separate entrances into the home—perfect for flexibility, guests, or everyday functionality.The heart of the home is the expansive kitchen, loaded with counter space and ready for your personal touch and creative design. Just off the kitchen, the family room features soaring vaulted ceilings and a cozy fireplace, creating a warm and inviting space to gather or unwind.Step outside and you’ll fall in love with the lifestyle this property offers… a screened-in porch for peaceful mornings, a spacious deck for entertaining, and a private backyard surrounded by nature.If you’ve been searching for space, privacy, and a home that feels like a retreat, this is it.

Rambling rancher on an established 3/4 acre garden in Country Club Estates with No HOA fees has extensive recent renovations: New architectural shingle Roof, New Heat pump, Stainless Kitchen appliances, New Bathroom fixtures, New Porch screening, New doors, New Ring video doorbell, ceiling lights and switches, Fresh paint and 6 New windows brighten a Basement Family room with 18” porcelain tile. A 40’ x 26’ block 2-car Garage with New insulated doors & openers, built-in shelving, jalousie windows, storage loft and 50% garage extension for Workshop as potential hobby space, home-based business or sporting gear cave. The Garage faces a private parking pad behind the home and a U-shaped driveway to a drive-through carport has the rear door entering a large Foyer convenient for bring in the groceries to the custom built Kitchen with a work-triangle layout. Finishing touches to the renovations are nearly complete, just choose the bedroom Carpeting and move into your New Home! Living Room: Walk along the slate flagstone path and pass through the New, classic Front Door into a spacious Living room featuring an elegant Fireplace and Hardwood floors that extend through a wide open Archway into the Dining room which opens to a comfortable screened Porch—the perfect spot to relax and enjoy the Garden view in this Prestigious neighborhood. Bedrooms: The main floor has a secluded Bedroom Wing with Hardwood floors and full Bathroom with 2 linen closets. A second Bathroom is conveniently close to Foyer and stairwell to Basement: The full Basement features an open Family room with brand-new windows that allow plenty of natural light inside. A side room equipped with a new sump pump well is a perfect blank canvas offering for an Office, Storage or a Rec room. Mechanical & Utillity Room: Separate Electric water heater from Oil boiler to provide comfortable hot water baseboard heat which is supplemented by a new HVAC system for Efficient heating and cooling. Enjoy Resort-like living in this Brick Ranch house only a chip shot away from the Chester River Yacht and Country Club with scenic river views while taking your neighborhood walks, And 5 minute drives along the Chester River, coming and going from your New Home to Historic Chestertown shopping and dining district, also well known for Live Arts, Festivals and home to Washington College.

Amazing end-unit townhome with breathtaking unobstructed views of the C&D Canal in the North Side of Historic Chesapeake City! Offering 2,200+ sq. ft. of living space, this beautifully maintained home features 2 bedrooms, 2 full baths, and a layout designed to enjoy the waterfront lifestyle both inside and out.The main level with hardwood flooring offers a spacious living room with cathedral ceilings, kitchen with maple cabinetry, granite countertops, and black appliances, dining area, family room, and a bright sunroom/breakfast room overlooking the canal. Step outside to enjoy the composite deck with retractable awning, beautiful gardens, and fenced rear yard — all perfectly positioned to watch the ships pass by.The upper level currently offers 2 bedrooms with a spacious sitting room, but could easily be converted into a 3-bedroom home by installing a wall in the existing opening between the rooms. Additional features include heat pump, public water and sewer, detached carport with locking storage shed, and numerous updates within the last 2–7 years, including the hot water heater, roof, and replacement windows. The dining room and bedroom windows also feature noise-reduction upgrades. The monthly maintenance fee is $125 and includes grass cutting, snow plowing, tick and mosquito treatment, and weed/feed lawn applications — making for easy, low-maintenance living. Town taxes include trash. Walk to nearby Schaefer's Canal House, stroll or bike along the canal, and hop on the water taxi to South Chesapeake City for shopping, dining, and more. This end-unit waterfront-view townhome in Historic Chesapeake City is the lifestyle opportunity buyers wait for!

A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Chester River. Zoned residential or business. Completely updated in 2021. Metal roof. Loaded with character and charm.

Why wait to build? This move-in ready 3BR/2.5BA townhome is ready for you now at The Venue at Winchelsea, a vibrant 55+ community in Middletown. Unpack, settle in, and spend your summer enjoying the community amenities while someone else waits for construction to finish.Enter to find a dedicated study—perfect for a home office—and a convenient first-floor laundry. The gourmet kitchen shines with modern stainless steel appliances, sleek quartz countertops, 42” cabinetry, a wall oven, and gas cooktop. The open layout flows seamlessly into the dining and living areas, with an included patio to enjoy unwinding during the upcoming spring and summer months. The first-floor owner’s suite is a peaceful retreat with a private bath and spacious walk-in closet.Upstairs, two additional bedrooms, a full bath, and a versatile loft provide comfort and privacy for guests. Schedule your private tour today!!Community Highlights:This 55+ Active Adult neighborhood features a 5,400 sq. ft. clubhouse, pickleball, tennis, bocce, swimming pool, fitness center, and more. Lawn care, snow removal, trash, and recycling are all included—leaving you free to enjoy the lifestyle you’ve been waiting for.Pictures are of model home and for representational purposes only. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit. For tours and open houses, visit the model home at 2405 Greyfriar Loop.

Back on the market at no fault of seller. Rigbie Bluff is the perfect maintenance-free community in the quiet waterfront town of Betterton; known as the Jewel of the Chesapeake. Located at the confluence of the Sassafras River and Chesapeake Bay, Betterton got its reputation for its picturesque sunsets and wonderful public beach. Embrace the waterfront lifestyle and so much more without the waterfront taxes. This 3 bedroom, 2 bathroom unit is being sold fully furnished and with a deep water boat slip, boat lift and jet-ski lift. As one of the larger units; it has plenty of room for the whole family. Natural light abounds with water views from both balconies or anywhere inside. Galley kitchen with granite countertops and stainless steel appliances. The main floor has an open floor plan, two bedrooms and a full bathroom. Large primary bedroom with ensuite bath and office space upstairs. Plenty of closet space throughout. Full basement has plenty of room for storing outdoor toys and equipment. Recent upgrades include: primary bathroom remodel, waterproof luxury vinyl plank flooring (original hardwoods underneath), carpets, Anderson windows, washer/dryer, water heater, interior doors, paint, and much more. Condo Association just finished renovating the decks and siding. Condo amenities include: private pier with water and electric, designated boat slip with 6,000 pound lift, community pool and kayak storage. Just a few steps from the water. This is the perfect weekend getaway or primary residence on the Eastern shore. Come see all that the Jewel of the Chesapeake has to offer.

Price improvement! Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a few minutes to historic downtown Chestertown.

NEW ROOF -- NEW CARPET-- ALL NEW INSULATION AND FLOOR VAPOR BARRIER IN CRAWL SPACE-- NEW PAINT IN UPSTAIRS HALL, STAIR WAY , FOYER, KITCHEN AND FAMILY ROOM !!Welcome to 29184 Corbin Parkway located in Easton Maryland. Colonial offering a lovely sunroom with tray ceiling and tile floors and door to the back patio. Family room with gas fireplace. Kitchen with sile stone counter tops. The master suite/bath with soaking tub and separate shower. Two additional bedrooms and bath on second floor.Nice two car garage with area for workshop-- carpet and overhead lighting. Enjoy your evenings relaxing on your back patio and watching wildlife. Beautiful flower beds in back the front yards. Invisible Fence front and back yards. All you need for this to be your home is your Family and belongings

*****PRICED $30,000 UNDER THE RECENT APPRAISED VALUE***** One floor living, a wood burning fireplace, and hardwood floors help this represent the cozy but elevated Eastern Shore lifestyle. The Mile Tree Village community is tucked on a quiet cul-de-sac with views of the Chester River. The home has been thoughtfully improved with major 2021 updates including joist replacement, flooring, crawl space encapsulation, and rear fencing all performed by the greatest hits list of Kent County craftsmen, along with freshly stained rough-cut cedar siding in 2025. An oversized two-car garage, serene courtyard with water feature, and a spacious, partially shaded backyard with deck seating create a setting that feels both private and inviting—all just a short walk to downtown shops, restaurants, Washington College, and the town’s parks.

Discover this spacious home offering 3,100 sq ft of living space on a ½ acre lot with deeded access to the Chester River. Generously sized rooms and an inviting floor plan create an ideal setting for both everyday living and entertaining. The main level bedroom features a recently remodeled bath and large walk in closet. Enjoy the natural light and tranquil views from the sunroom, perfect for relaxing year-round.*New roof has been installed!

Welcome to 14 Blue Spruce Way in the highly desirable Ridgely Forest community! This like-new home is proudly offered by the original owners and features one of the rare 5-bedroom, 2.5-bathroom floor plans in the neighborhood.Situated on a corner lot, the backyard is fully enclosed with a privacy fence and features a beautiful custom deck, perfect for relaxing or entertaining on summer weekends.Inside, you’ll find granite countertops, a spacious kitchen, and a large living room ideal for gatherings. The unfinished basement offers endless possibilities for additional living space, a home gym, or recreation area.Additional features include a 2-car attached garage and access to the community swimming pool.Conveniently located just minutes from Elkton and North East, with quick access to major highways for easy commuting.

Adorable updated cottage in the heart of town on popular Bayside Avenue offering approximately 1,400 sq. ft. of charming coastal living. This delightful Cape Cod features 3 bedrooms and 2 full baths, with seasonal water views of Rock Hall Harbor from the second floor. The main level offers an open floor plan with a cozy propane fireplace, 2 bedrooms, and 1 full bath, while the entire upper level serves as a spacious private primary suite.Enjoy outdoor living in the fenced rear yard — perfect for pets, entertaining, or relaxing on the back deck while taking in the scenery. A detached one-car garage and storage shed provide plenty of room for bikes, tools, kayaks, and LSV/golf cart storage.Ideally located within walking distance to local favorites including Harbor Shack and Waterman’s Crab House, marinas, harbor festivities, shops, and more. Conveniently situated along the complimentary Rock Hall Rides shuttle route, making it easy to enjoy everything this waterfront town has to offer!

COMING SOON - NEW ROOF!!! Your Chesapeake Bay getaway just steps from Haven Harbour South Marina. Launch your boat, dine on the waterfront, stroll to the beach, and enjoy resort-style living from this beautifully updated home. This updated 3-bedroom, 2-bath rancher situated on an expansive lot with glimpses of the water and room to relax, entertain, and enjoy the Eastern Shore lifestyle. The spacious detached garage provides ample storage for vehicles, boats, and recreational equipment. Unwind in the cooled three-season room overlooking the fenced backyard, offering the perfect setting for gatherings with family and friends after a day on the water. Ideally located just a short walk or golf cart ride from Haven Harbour South Marina, you'll enjoy convenient access to boat slips, waterfront dining, a sandy beach, marina amenities, and breathtaking Chesapeake Bay sunsets. Whether you're seeking a year-round residence, weekend escape, or boating retreat, this property offers comfort, convenience, and the best of Rock Hall living.Wake up, walk to your boat, spend the day on the Chesapeake Bay, enjoy waterfront dining, watch the sunset, and return home to relax in your private backyard. Every day feels like you're on vacation.

Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updated appliances, ample cabinet storage, and a breakfast bar. The primary suite has a large walk-in closet and an en-suite bath which now boasts a soaking tub. Step outside to enjoy the large deck, fire pit patio, and fully fenced backyard. This home offers comfort and convenience at every turn. Just a few blocks from Washington College and a short stroll to Downtown Chestertown’s charming restaurants, shops, and waterfront.

Fully furnished! Adorable rancher in a PRIME location in Rock Hall. Just steps to the marinas, restaurants, and shops. The house has been completely remodeled. All new appliances. Large family room with a pellet stove and plenty of space for social gatherings. Nice-sized bedrooms and 2 full bathrooms. Luxury vinyl plank flooring throughout. Detached garage and potting shed. Less than 1/2 mile to the public beach. Private backyard with koi pond and water feature. The current owners have their boat docked at a nearby slip, and they can see it from the property. There is no work to be done here. Just bring a suitcase and move right in!

GREAT NEW PRICE!Why wait for new construction when this practically brand-new home is move-in ready? 4 Bedrooms 2.5 Bathrooms 2-Car Garage. Located in the sought-after Ridgely Forest community! Step inside to an open floor plan featuring stunning vinyl plank flooring on the main level and fresh paint throughout. Cozy up around the shiplap fireplace centerpiece—perfect for entertaining! The main level offers a versatile space ideal for a home office or guest bedroom. Upstairs, enjoy the convenience of second-floor laundry and spacious bedrooms with plush carpeting. The primary suite boasts a gorgeous accent wall, a large walk-in closet, and a beautiful ensuite bathroom. Your backyard oasis awaits—just add your personal touches to make it your own. The unfinished basement offers endless possibilities for additional living or recreation space. Entertain with ease in the kitchen that opens seamlessly to your living and dining areas—perfect for hosting friends and family! Don't miss this opportunity to own a stunning home in a fantastic location—schedule your showing today!

Welcome to 1824 Price Station Rd—a 3 bedroom, 2 full bath home offering space, updates, and versatility in a highly convenient location. Situated on a generous homesite in Church Hill and surrounded by scenic farmland, this property enjoys a truly bucolic setting while remaining just minutes from Rt. 301 for an easy commute. Inside, the home features updated flooring throughout, along with a newer kitchen and baths that blend modern finishes with everyday practicality. The spacious eat-in kitchen serves as the heart of the home, complete with a slider door providing access to a spacious deck overlooking the level, private backyard setting—perfect for everyday living and entertaining. A spacious sitting area provides the ideal place for relaxing or hosting guests. The layout flows comfortably with abundant natural light enhancing the interior spaces. The primary suite includes a large private bath, offering a comfortable and private retreat. Step outside to enjoy the peaceful surroundings, where the meticulously landscaped grounds and mature plantings frame the backyard and provide a sense of privacy. The expansive driveway offers a large parking area at the home, along with an additional oversized parking area in front of the detached building—ideal for accommodating multiple vehicles, boats, RVs, and more. A standout feature of the property is the oversized detached building, complete with two spacious bays and a dedicated workshop area. This versatile structure is insulated, heated, and includes plumbing—perfect for hobbyists, contractors, or anyone in need of additional workspace or storage. Offering the perfect balance of rural charm, functionality, and commuter convenience, this property is a rare opportunity to enjoy country living with room to spread out. Mortgage savings may be available for buyers of this listing.