Stunning 2 bedroom waterfront guest house just a short walk from Chestertown's historic district. Top to bottom exceptional interior design and brand new finishes from Stoltzfus Brothers Construction. Enjoy summer sunsets of the Chester River and Chestertown's timeless waterfront or take advantage of the dock and private water access. This guesthouse truly celebrates the water views from any angle. It was custom built and designed for the owners to live in down the road, and the care and craftsmanship shows in every detail. First floor features a large living room, private deck, upgraded kitchen and bedroom and full bath. Second floor is the oversized primary bedroom with ensuite bath and plenty of closets and storage space. Quiet and private waterfront location yet just a few minutes walk to downtown shopping and restaurants. All utilities included in rent: electric, propane, trash, water, sewer. Tenant just pays internet and tv. Final landscaping and window treatments are being done currently. Professional photos coming soon. Available second week of May.

Invest in improving your quality of life with one of the last remaining homesites in Char Nor Manor, a water oriented community on the Chester River. At over a half acre, this allows space for many possibilities. Just across the street from the wetlands and river, this property embodies the Eastern Shore lifestyle. A soil evaluation has already been performed with favorable results. A buyer would need to get a property survey recorded to take the last steps for the perc approval. This community is located just minutes from the shops and restaurants of Chestertown and less than 2 hours from Philadelphia, Baltimore, and Washington DC.

Come build your dream home. Located right off E Sharp Street on Chesapeake Villa is your .46 acre lot. Location is perfect to everything Rock Hall has to offer, from shops to restaurants to the water. Come check it out today.Lot has water/sewer hookup available, contact town of rock hall to confirm fees.

PRICE REDUCTION!!Wonderful lot in Betterton, only 2 blocks from the beach, and your chance to make wonderful memories in this community known as the Jewel of the Chesapeake. Betterton sits right on the upper Chesapeake Bay at the mouth of the Sassafras River, an extremely popular boating area. The beach is beautiful with calm waters and amenities for a perfect day at the beach. This community is certainly a treasure and one of the areas best kept secrets! Don't miss out on your chance to build your dream home in one of the best little spots in Maryland! Water/Sewer Allocation is available through the town.

Discover the perfect opportunity to build your dream home on this stunning 4.97-acre waterfront lot on Brooks Creek—offering the rare advantage of no HOA restrictions. This deep-water, approved residential building lot features a recorded plat and has already been perc tested, making it ready for your plans. A bermed infiltration pond (BIP) for sewer is installed and shared with the adjoining lot. Enjoy good water depth with quick, easy access to the Chesapeake Bay, ideal for boating, crabbing, and fishing.Nature lovers and outdoor enthusiasts will appreciate the abundant wildlife, including deer, turkey, waterfowl, blue heron, osprey, and bald eagles.Located just 20 minutes from Cambridge and under two hours from Washington, D.C. and Baltimore, this property offers the perfect balance of seclusion and accessibility. Whether you're looking to build a full-time residence or a private getaway, this exceptional waterfront lot is ready to bring your vision to life.Call today for additional informaion.

Affordable lot rent! This 3-bedroom, 2 full bath double-wide rancher is located in Forest Glen Court and offers comfortable one-level living. Featuring vaulted ceilings, a spacious kitchen with a large center island, and a functional layout, this home is a great opportunity.Ground rent is $525 per month and includes sewer and snow removal on the streets. Buyer must receive park approval from Forest Glen Court.

This is a unique opportunity to invest in cleared and level acreage just off one of the Eastern Shore's commercial corridors and a few minutes from Downtown Chestertown. Suburban Commercial Zoning allows for a variety of possible uses.

Welcome to this sweet ranch-style home in Worton, Maryland, tucked into a quiet little neighborhood of Knight’s Landing surrounded by beautiful farmland. It’s the perfect spot if you’re looking for peaceful living without feeling far from everything—just under five minutes to the local high school, community center, and park. Cozy, convenient, and easy on the budget, this home offers small-town vibes with everyday essentials close by.Property sold AS- IS Seller will make NO REPAIRS

Enjoy coastal living this fall and beyond with this meticulously maintained, fully furnished, turn-key 1-bedroom, 1-bath condo in Ocean City, MD. Perfectly situated on the first floor, you’ll appreciate the ease of access—no stairs to climb when bringing in luggage or supplies. Inside, the open-concept kitchen and living area provide a bright, welcoming space to relax or entertain. Step outside to your spacious balcony, complete with comfortable furniture, hurricane shutters, and a convenient storage shed for beach gear and toys. Recent upgrades include a new washer/dryer (2023), refrigerator (2019), and a Google Nest thermostat that allows you to control the climate remotely. After a day at the beach, rinse off in the community’s outdoor shower before heading inside. Parking is included for added convenience.Just two short blocks from the ocean and within walking distance to the historic Ocean City Boardwalk, Jolly Roger Amusement & Splash Mountain Water Park, plus countless restaurants and shops—this location offers the best of everything. The Jamaica Daybreak Condo Association recently completed extensive exterior renovations (May 2025), with all assessment fees already paid in full by the seller—giving buyers peace of mind. With some of the lowest condo fees in the area at just $325/month, you’ll also enjoy discounted cable TV and internet. Lovingly owned for 20 years and never rented, this condo is move-in ready and waiting for its next chapter.

Welcome home to this charming 3-bedroom, 1.5-bath property ideally situated on a corner lot just a short walk from downtown Hebron. Inside, you’ll find a flexible layout featuring additional bonus spaces—perfect for a home office, playroom, or guest area. Enjoy peace of mind with thoughtful upgrades including a tankless hot water system, encapsulated crawlspace, insulated attic, and hardwired high-speed internet. Step outside to a fully fenced backyard with a 6-foot privacy fence—ideal for relaxing or entertaining.

Looking for a 3 bed farmhouse in Millington with classic charm and modern updates? This warm and friendly 1920 single family home offers 1508 square feet on a 0.17 acre lot with a 2021 roof, vinyl siding, three second floor bedrooms, one full bath, and a half bath off the kitchen. A wrapped front and side porch sets the tone, while a rear wooden deck opens to the yard for easy outdoor living. The heated rear garage includes driveway parking and a setup that allows welder hookup, ideal for hobby work or small trades. Inside, the layout provides a cozy front living space, practical kitchen flow, and natural light throughout. Located in Millington with quick access to Route 301.

Seller has to find home of choice. Welcome home to this charming 2-bedroom, 1-bath gem nestled in a quiet, established neighborhood. Perfect for first-time buyers, downsizers, or anyone looking for comfortable, low-maintenance living, this home offers both warmth and functionality.Step inside to find beautiful new wood flooring flowing through the living room, kitchen, and hallway, creating a fresh and modern feel throughout the main living areas. The spacious living room is ideal for relaxing or entertaining guests, while the kitchen offers plenty of room to cook and gather.The oversized primary bedroom is a true retreat, featuring a generous walk-in closet with ample storage space. A well-appointed second bedroom provides flexibility for guests, a home office, or additional family members.Situated on a .4-acre lot, the fully fenced backyard offers privacy and room to enjoy the outdoors. Spend summer days cooling off in the above-ground pool, hosting barbecues, or simply unwinding in your own private space.With its inviting layout, recent updates, and convenient location, this home is ready for you to move in and make it your own.

Welcome to life in Rock Hall — a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living.This lovingly renovated home was thoughtfully updated by owners who cared about the details—not a quick flip—resulting in a property full of character and quality improvements throughout. Inside, you’ll find beautiful LVP flooring, a bright open-concept layout, and a stunning kitchen featuring granite countertops, a tile backsplash, stainless steel appliances, and plenty of space to gather after a day on the water, experiencing Chestertown and all the other towns nearby! Owner had a pre home inspection for your convenance! The home is good to go!For peace of mind, all major systems are new, including a brand-new roof, and a home inspection has already been completed with items addressed, making this home truly move-in ready.The layout offers comfort and privacy with the primary suite tucked away on one side of the home, while the three additional bedrooms are located on the opposite side, perfect for maybe or a home office setup. The home is connected to public water and sewer, and also offers fiber internet, giving you modern convenience in a laid-back coastal setting.Step outside and enjoy the freedom that comes with no restrictions—bring your boat, RV, or water toys, and if you’ve been dreaming of building a pole barn or workshop, you can do that here too.Located just minutes from creeks, rivers, and the Chesapeake Bay, this home places you right in the heart of one of the Eastern Shore’s most beloved boating towns. Rock Hall may only have one traffic light, but it’s full of life—with marinas, waterfront restaurants, coffee shops, boutiques, ice cream stops, and a quaint downtown. The town hosts events throughout the year, creating that true small-town vibe where everyone knows your name—or soon will.If you’ve been searching for a fun, beachy lifestyle with small-town charm, modern updates, and room for your boats and hobbies, this home delivers.Rock Hall — where nice people live.

Highly sought after large townhome in the desirable community of Mallard Landing in Denton, featuring almost double the square footage, and a rear deck off of the kitchen. Multi-generational living has a full bedroom and bath, as well as a large family room on the main floor. A few easy steps to the second floor brings you to a beautiful open kitchen, dining, and living room. The third floor features two more bedrooms sharing a full bath, as well as a large primary bedroom with en suite. New flooring throughout. Community pool and playgrounds make this home desirable for all ages. Easy highway access makes commuting a breeze, or in-home office space for working from home is also an option. Easy walking to the new brewery or local pub where friends and neighbors gather to break bread and share a pint. This homes location has it all.

Easton charm meets everyday convenience at this coming soon opportunity at 207 Tred Avon Avenue. Ideally located just moments from downtown Easton’s shops, restaurants, galleries, and this home offers the chance to enjoy in-town living with character and comfort.Upon arrival, a versatile den welcomes you into this charming bungalow - use it for an office, tv room, play area, or just a relaxing space to greet guests. Venture into the living room with built in shelving and decorative fireplace mantel.Off the living room, you'll find the primary bedroom with ample closet space and primary bath with a linen closet and access to the attic for additional storage space.Through the living room, you'll find a bright kitchen and dining room. The kitchen has lots of cabinets for storage, a built-in microwave with exhaust fan, and side door that goes right to the driveway for easy access to carry in your groceries. The laundry closet is right off the kitchen and large dining space. Two bedrooms and a second bath with an additional linen closet round out the interior features of the home.The backyard is a practically a blank slate to make your own. New fencing has recently been added and a small portion of the yard was already sectioned off for a pet area which could easily be converted into an elevated garden or entertaining space. A nice shed will convey with the property as well. There is ample space to add a patio for outdoor entertaining, carport, or even a garage (buyers to do their own due diligence for building regulations, permitting, etc.)The heat pump and air handler were recently renewed with a new compressor and new blower, and a new roof was installed in 2024. This motivated seller is offering a $5,000 closing credit for a flooring allowance with a fair and reasonable offer.Whether you're sipping coffee in the cozy den or headed into town for a night out, this home is the ideal spot to call your own.

Charming 3-Bedroom Rancher in an Ideal Easton Location!Nestled in a prime Easton location, 16 Willis Avenue offers the perfect combination of comfort, convenience, and charm. This well-maintained 3-bedroom, 1-bath rancher is situated on a desirable corner lot, just a stone's throw from the heart of Easton. Whether you're looking for a great starter home or a cozy space to downsize, this property has something for everyone.The thoughtfully designed layout includes a spacious living room with a large windows allowing for ample natural light with a separate dining room that leads into a well-equipped kitchen that includes a full-size washer and dryer. Hardwood floors can be found throughout the home. Three bedrooms and one bath complete the interior layout of this quaint in-town Easton home.From the kitchen, step outside to a screened-in porch, the perfect spot for enjoying your morning coffee, unwinding after a long day, or hosting friends and family for a gathering, all while staying cool and bug-free. Enjoy the privacy and spaciousness of a corner lot, offering ample outdoor space for gardening or simply relaxing in the fresh air.One of the highlights of this home is its proximity to downtown Easton, where you’ll find charming shops, dining, entertainment and year round events and festivals. Enjoy all the benefits of town living while still having the peace and quiet of a residential neighborhood.With neutral colors throughout and easy-to-care-for features, it’s perfect for anyone looking for a low-maintenance, move-in ready property.Whether you're starting out, downsizing, or looking for a peaceful retreat, this home offers great value in one of the most desirable locations on the Eastern Shore. Don't miss your opportunity to make this house your home!

​Discover the perfect blend of comfort and convenience in this lovely home located in the desirable Buckhill Farms community of Elkton, MD. Whether you are commuting to Delaware or hopping on I-95, this location makes travel a breeze while offering a peaceful suburban retreat.​Step inside to find a welcoming upper level featuring beautiful hardwood floors that flow throughout the main living areas. The open-concept living and dining room creates an inviting atmosphere for entertaining, with direct access to your private back deck—perfect for morning coffee or summer BBQs. The kitchen offers a functional layout with plenty of space for meal prep and storage. This home features three well-appointed bedrooms on the upper level, all served by a spacious full bathroom. The partially finished lower level adds incredible value and flexibility to the home. Currently utilized as an additional bedroom and a dedicated office space, this area is ideal for guests, hobbies, or working from home. You will also find: ​A second full bathroom for added convenience, an oversized laundry room with extra space for storage or organization. Enjoy peace of mind in the fully fenced-in backyard, providing a secure and spacious area for play, gardening, or relaxing in the fresh air.​Don’t miss your chance to own this versatile home in a prime Maryland location!

PROFESSIONAL PHOTOS COMING!!!! Water-oriented living at its best! This charming 2-bedroom, 1 full bath home offers approximately **1,100+/- sq. ft.** and is loaded with features buyers are looking for! Kitchen with granite counters, stainless steel appliances and counter bar seating, spacious bath with double sinks and a **jetted tub/shower combo**, vinyl tilt windows, central air, heat pump, one-car garage, and a spacious **24x12 rear deck** perfect for entertaining. Whole house custom plantation blinds.Situated on a beautiful corner lot, this property comes with **deeded private beach, water and mooring rights**—a rare find! Enjoy the fenced concrete rear yard, welcoming front porch, and step outside to enjoy being just moments from the water. Perfect for **first-time buyers, downsizing, a weekend retreat or year-round living**… this one checks so many boxes.

Welcome to this spacious end-unit townhouse offering 4 bedrooms and 2.5 bathrooms, providing plenty of room for comfortable living. The main level features a bright and open layout with abundant natural light, ideal for everyday living and entertaining. The kitchen opens to the main living areas, creating a functional and inviting space.Upstairs, you’ll find generously sized bedrooms, including a primary suite with a private bathroom. Additional bedrooms offer flexibility for guests, a home office, or playroom. Enjoy the convenience of low-maintenance living while being just minutes from downtown Easton, shopping, dining, and parks. This home is a great opportunity for anyone looking for space, comfort, and a prime location on Maryland’s Eastern Shore.

Take advantage of this irresistible opportunity to purchase 12 acres with 2 houses, a few outbuildings and a ton of potential. The property is located just off of Route 301, the Eastern Shore's main thoroughfare. The location is perfect for commuters looking to improve their quality of life or someone looking for a homestead close to Chestertown's waterfront historic district. The property is less than an hour from Annapolis, a half hour from Middletown, and within 2 hours of DC, Philadelphia and Baltimore. This property is being sold As-Is.

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in the desirable Woodsedge community. Situated on a spacious corner lot, this property offers both privacy and curb appeal with plenty of outdoor space to enjoy. Inside, you’ll find a thoughtfully designed layout perfect for everyday living and entertaining. The home features a bright and inviting living area that flows seamlessly into the kitchen and dining spaces.The primary bedroom serves as a comfortable retreat, complete with a full en-suite bathroom and two generously sized closets providing ample storage. Three additional bedrooms offer flexibility for family, guests, or a home office.Step outside to a rear deck overlooking the yard, ideal for relaxing evenings, outdoor dining, or weekend gatherings. The attached garage adds convenience and extra storage space.With its prime location in Woodsedge, functional layout, and attractive features, this home offers the perfect blend of comfort and practicality. Don’t miss the opportunity to make this corner-lot gem your own.

Charming and move-in ready, this beautifully maintained 2-bedroom, 1 full bath ranch sits on a spacious .46-acre lot and offers 1,219 sq. ft. of comfortable living space. Step inside to an inviting living room featuring a cozy propane fireplace, updated flooring, and fresh paint throughout. The kitchen and bathroom have been tastefully updated, and like-new appliances make this home truly turnkey. Septic inspection completed, along with a newer well pump and tank for added peace of mind.Enjoy the convenience of a utility room and mudroom connecting directly to the attached garage, along with vinyl tilt-in windows for easy maintenance and efficiency. A heat pump with oil backup and central air provide year-round comfort. The home features a crawl space (no basement), and the roof is approximately 7 years old. The living room only has been virtually staged with furniture to help give you a vision of the space and its potential.✨ If you’ve been looking for a well-cared-for home with space, updates, and value—this is it!

LET'S MAKE A DEAL!!! Come see this beautifully renovated ranch-style home offering over 1,431 sq. ft. of living space, ideally located on a quiet back street in a desirable water-oriented community with beach access.This 3-bedroom, 1 full bath home was completely renovated down to the studs in 2021, allowing the next owner to enjoy the benefits of extensive upgrades throughout. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating a functional and inviting living space.The kitchen features white cabinetry, black granite countertops, and GE stainless steel appliances, while the home is enhanced by ¾-inch thick, 3-inch wide sanded and stained hardwood floors. A spacious family room offers a wood stove and slate flooring, providing additional living and entertaining space.Major improvements include all new plumbing and electrical systems (2021), Andersen Low-E windows, and a Pella sliding door with built-in blinds in the primary bedroom. The updated full bath features a tile surround, and the home is equipped with a high-efficiency Amana heat pump, 50-year architectural shingles, and updated siding.Additional highlights include a stackable washer and dryer, a large front deck, storage shed, and seasonal water views. Residents enjoy access to community amenities including boating, watersports, and beach access.A thoughtfully renovated, move-in-ready home offering comfort, quality, and lifestyle in a waterfront community.

Colonial in Kennedyville overlooking the pond. Situated on a corner lot with a private driveway behind the house. 2 car attached garage, 4 bedrooms and 2.5 baths. Gas fireplace. Large mudroom with laundry. Partially finished basement with new carpeting. Lovely front porch for relaxing and enjoying the view.

Tucked away just outside of town, this charming 3-bedroom, 2-bathroom home offers the perfect blend of privacy and space on a beautiful 4-acre property. The land features a mix of open, cleared yard and mature woods, providing both room to roam and a peaceful natural setting.Inside, the home offers a comfortable and functional layout, ideal for everyday living. One of the bedrooms includes a unique addition that was previously used as an art room, offering endless possibilities as a creative studio, home office, or private retreat.Outside, the property truly shines. A spacious 3-car garage provides plenty of room for vehicles, storage, or a workshop. The screened-in gazebo is the perfect spot for relaxing or hosting gatherings, whether you're enjoying summer evenings with family or spreading out a feast of steamed crabs with friends.With its quiet location, versatile spaces, and scenic surroundings, this property offers a rare opportunity to enjoy country living while still being within reach of town conveniences.

COMING SOON!!!!!Nestled in the heart of Maryland’s Lower Eastern Shore, 1151 Crocheron Road in Toddvilleoffers a rare opportunity to own a property surrounded by nature, privacy, and authenticEastern Shore charm.This home is perfectly positioned for those seeking peace, space, and outdoor living. Withabundant wildlife, open surroundings, and a quiet rural setting, the property is especiallyappealing to hunters and outdoor enthusiasts, with frequent sightings of deer and nativewildlife right on and around the property.Toddville is known for its rich watermen heritage, natural beauty, and unspoiledlandscapes—making it an ideal location for a primary residence, weekend retreat, orrecreational getaway. Whether you’re envisioning a hunting basecamp, a private escape, or aplace to enjoy the slower pace of coastal living, this property offers the flexibility to bring yourvision to life. 4 bedrooms, 2 full Bathrooms, newly remodeled kitchen, fenced yard and so many more wondeful features.Enjoy the freedom of country living while still being connected to nearby towns, waterways,and the unique lifestyle that makes the Eastern Shore so special.

Nestled in the charming Allwood community, this beautifully renovated ranch-style home offers a perfect blend of comfort and modern living. Built in 1971 and thoughtfully updated in 2022, this residence boasts 1,440 square feet of well-designed space, ideal for creating lasting memories. Step inside to discover an inviting open floor plan that seamlessly connects the living room, kitchen and dining area, and straight through to the family room, making it perfect for gatherings and entertaining. The kitchen features a sleek modern style, equipped with newer shaker cabinets and a combination of butcher block and solid surface countertops. Modern appliances include a built-in microwave, gas oven/range, and a dishwasher, ensuring meal prep and clean-up is a breeze. The home includes a spacious primary suite, featuring a remodeled bathroom, with tiled walk-in shower and laundry area. Two other nice sized bedrooms and another remodeled bath with a tub/shower. Additional interior highlights include in-wall soundproofing, luxury vinyl plank flooring, ceiling fans for comfort, and upgraded triple-pane windows that enhance energy efficiency. Outside, the property is equally impressive. The exterior showcases a combination of brick and newer vinyl siding, newer roof, and front landscaping. Enjoy the outdoors on the patio area and utilize the covered carport area as a great gathering location, perfect for that summer crab feast! (Please note the deck shown in the pictures was removed). The Allwood community is known for its friendly atmosphere and convenient access to local amenities. Residents enjoy nearby parks, perfect for leisurely strolls or picnics, and a variety of shopping and dining options just a short drive away. Commuting for work is a breeze..only minutes away from I-97 and Rt. 100. Experience the comfort and warmth of this exceptional property, where every detail has been thoughtfully considered to create a true sense of home. Make it your home and schedule a tour today!

A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.**See updated zoning info from the town in documents

A Rare Opportunity in the Heart of Historic ChestertownDiscover a truly special offering in the vibrant core of Chestertown’s Historic and Arts & Entertainment Districts. Owned by the same family for over 50 years, this multi-family property sits on a generous double lot known historically as the Laurence Lots—featured on original town maps and steeped in local heritage.Brimming with character and potential, the property currently features a townhouse on one side and two apartments on the other, offering a flexible layout ideal for renovation, income generation, or a creative reimagining. Whether you're envisioning a stately single-family residence, a dynamic live/work space, or a thoughtfully restored multi-unit investment, the possibilities are as expansive as the lot itself.That said, this is not a turnkey property. Significant settling has occurred over the years, and a substantial renovation will be required to bring it back to life. Offered strictly as-is, this is a true fixer-upper for the visionary buyer ready to take on a transformative project.Situated within both the Arts & Entertainment District and Enterprise Zone, this location supports both residential and business uses—making it an ideal candidate for those looking to merge lifestyle, business, and history. **See updated zoning info and description from town office in Documents.Bring your vision, creativity, and tools—and seize the chance to breathe new life into a piece of Chestertown’s storied past. Opportunities like this don’t come along often.Schedule your showing today and imagine the future you can build here.

Remarkable remodel in the heart of Easton. Brand new everything from the studs out. Large open floorplan centered around the thoughtfully designed kitchen featuring a huge island, stainless steel appliances and close quiet cabinetry makes the heart of this home sing. Step outside to enjoy some after dinner cocktails on your beautiful brick patio with views of the Tred Avon River. Huge primary suite includes walk-in closet and en suite with walk-in shower. Central AC and Heat with mini splits in the back half help keep costs and temperature controlled. Seamlessly blending new and old charm, come see this whimsical home quickly

Nestled on a desirable corner lot in Easton, this charming 3-bedroom, 2.5-bath home offers the perfect blend of comfort, convenience, and location. Just a short distance from a scenic walking trail, it’s ideal for those who enjoy outdoor strolls, morning jogs, or peaceful evenings surrounded by nature.Inside, the home features a functional and inviting layout with spacious living areas, perfect for both everyday living and entertaining. The kitchen flows seamlessly into the dining and living spaces, creating a warm and connected atmosphere. Central heating and air conditioning ensure year-round comfort no matter the season.Upstairs, you’ll find three well-sized bedrooms, including a primary suite with a private full bath. An additional full bathroom and a convenient half bath provide ample space for family and guests.Step outside to enjoy the rear deck, perfect for grilling, relaxing, or hosting gatherings. The attached garage adds convenience and extra storage.Located just minutes from downtown, you’ll have easy access to local shops, dining, and community events, making this home a wonderful opportunity to enjoy all that Easton has to offer.

Sweet Victorian in downtown Betterton, just a short walk to Betterton Beach. Home has been lovingly cared for by the same owners for nearly 50 years. The main floor features the living room, dining room, and kitchen. As well as a laundry room with half bath, an office, an entry room in the front, and mud room in the back. On the second floor you will find 3 bedrooms and a full bath. On the 3rd floor is another bedroom that could also be used as a family room, hobby room or office. Out back, there is a driveway with parking for 2 cars. The rear yard is perfect for entertaining with a deck, patio and covered pergola. Brand new oil furnace. Mini splits in most of the rooms. This property is quaint and charming and would be perfect as a beach home or a full time residence.

Spacious home in Kenndyville with lots of amenities. Featuring 4 bedrooms and 2.5 baths with a large kitchen with granite countertops, living room with gas fireplace, 2-car detached garage, and a huge unfinished basement. Plenty of storage. Deck off the living room leads to a partially fenced back yard. Just a short drive to downtown Chestertown.

This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures.The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining.Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment.With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

*****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.

Welcome to 103 Trafford Drive; an exceptionally maintained 3 bedroom home just minutes from downtown Chestertown. Nestled in family-friendly Coventry Farms Community, this Colonial-style residence has been recently updated in all the right places for modern convenience and classic charm. A brand new kitchen, 5-inch oak hardwood floors, back patio, washer/dryer are just a few up the recent updates. Some of the timeless interior features include a wood burning fireplace, tray ceilings, baseboard and crown moldings, chair railings, . Inside you are greeted by a traditional layout with a formal dining room and formal living room or office space. The front of the home flows seamlessly to the back where the heart of the home is: the newly renovated kitchen and living room space punctuated with a wood-burning fireplace. Recent kitchen improvements include: custom maple wood cabinets, quartz countertops, Frigidaire and LG stainless steel appliances, and a reverse osmosis water treatment system. The spacious and private back yard has a thick tree line to the back and has been elevated by a new concrete patio and wood steps and newly planted pine trees for additional privacy. Going upstairs one will find brand new 5-inch red oak hardwood floor throughout: and no thresholds! The spacious primary bedroom features an ensuite bath with jetted soaking tub and an oversized walk-in closet. The full basement could easily be turned into a fourth bedroom with electric, lighting, ductwork, and roughed-in plumbing all ready to go. Oversized two-car garage offers additional storage or parking. Don't miss this opportunity. This stunning home has been meticulously maintained and upgraded in all the right spots; offering exceptional elegance and modern comfort. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals and an award-winning weekly Farmer's Market. Less than 90 minutes to Philadelphia and Washington D.C. Come see what Chestertown life is all about. Some furnishings may convey. PLEASE NOTE: Zillow's property taxes are incorrect: correct annual property taxes are $4,338.

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!

Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences.From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind.The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, and a completely updated kitchen with granite countertops and brand new stainless steel appliances. Both bathrooms have been tastefully renovated, offering a clean and modern feel while complementing the home’s historic charm.Additional highlights include a convenient laundry/mudroom off the rear of the home and a flexible third-floor loft space—ideal for a home office, playroom, or guest retreat.Out back, you’ll find a detached carriage house equipped with electric (100 amp service), heat, and A/C—perfect for a workshop, studio, or additional storage.Situated in the quaint town of Kennedyville, this property offers the perfect balance of historic character, modern upgrades, and small-town charm.

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.

Private backyard in Vibrant Community. Get lost in this backyard oasis close to downtown Easton in the very exciting neighborhood of Mulberry Station. Minutes from downtown Easton, you will get lost in all the special nooks and crannies hiding in your hidden paradise. Lose yourself in a book under the Crepe Myrtles, Zen out next to the manmade ponds with water features. Who needs a sound machine with the peaceful sounds of leaves rustling and babbling brooks babbling? A huge inground pool with a designated firepit area can make any evening special. This thoughtfully designed outdoor space needs to be seen to really be appreciated. Inside, you will find ample room to spread out. The lovely kitchen/family room combo features a gas fireplace to cozy up to. Indoor/Outdoor dining with sliders that open up from your kitchen onto your beautiful large deck with electric awning. Upstairs, Double doors open to your very large primary suite with walk-in closet and en-suite. Three other large bedrooms and bathroom round out the upstairs.

Welcome to the desirable Rivers End community, where lifestyle and location come together. Residents enjoy a community fishing pond, recreational area, along with neighborhood events and the convenience of golf cart–friendly streets.This spacious home offers 4 bedrooms (septic approved for 3) and a layout designed for comfortable living and entertaining. The large living room flows openly into the kitchen, creating a bright and welcoming gathering space complete with propane hookup. The kitchen features tile backsplash, under-cabinet lighting, a built-in computer desk, and updated appliances including a 2025 dishwasher, 2024 refrigerator, and a stove and microwave from 2018.A separate dining room with vaulted ceilings adds charm and elegance, while hardwood interior doors and vaulted ceilings in the bedrooms with French door closets add character throughout the home. The oversized primary suite features a wide double door sized entrance, large walk-in closet, LVP flooring, jetted soaking tub, and separate stall shower, creating a relaxing private retreat.The second-floor bonus room has been converted into an additional bedroom and sitting/play area, and another bedroom includes its own attached half bath, offering flexibility for guests or other members.Additional highlights include a large laundry room that doubles as a pantry with built-in storage, new smoke detectors, and a crawl space with plastic vapor barrier. Major systems have been thoughtfully maintained, including a dual-zone Trane HVAC system ( 2020 air handler) and a hot water heater approximately five years old. More is being updated ad upgraded as we go! Flooring credit offered & can be applied at settlement!The oversized garage offers extra room for storage or hobbies and is fully drywalled, with a generator outlet already in place. Outside, the private backyard features irrigation, providing a great space to relax or entertain.Enjoy fishing or small boating in the community pond, or take advantage of the location just outside Seaford, close to local seafood restaurants with easy access to the beaches close enough for a day trip. This home offers the perfect blend of space, community amenities, and convenient coastal living. The sale of this home is contingent on Seller settling on another home simultaneously with their home sale with a home that they currently have under contract.

Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester River. The welcoming foyer seamlessly flows into the rear den or office which could be converted into a 3rd bedroom. Off the den is the first-floor bedroom and full bath. Enjoy the summer breeze from the private back screened-in porch; recently upgraded with high-tech flex screens and a ceiling waterproofing; keeping the porch dry. The real action is found upstairs. The living room – anchored by an electric fireplace with stone surround – is complemented by the oversized second story deck; perfect for grilling or watching picturesque Chester River sunsets. The modern kitchen features new stainless-steel appliances, abundant cabinet space, granite countertops and a large island with breakfast bar. Plenty of space for formal or casual dining. The second floor is finished by an oversized primary bedroom with ensuite bath and large walk-in closet. Should one desire an elevator; there are two locations where one could be built into the existing design. Leave your worries aside as the condo association takes care of all exterior maintenance, yardwork, and repairs. Boaters will enjoy the well-maintained community dock with slips available for purchase or lease (with board approval), or just drop in a kayak or paddle board; great on warm summer evenings. Other community amenities include the pool, walking paths, garden, picnic and grilling areas, and a fire pit. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic architecture, local shopping, restaurants, art galleries, and waterfront walkways and parks. Chestertown is home to many festivals and an award-winning Farmer's Market every Saturday. New YMCA with full gym, racquet sports, lap pool, sauna, etc. Don’t miss your opportunity to enjoy worry-free living along the Chester River.

Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart of Queen Anne’s County. Surrounded by the natural beauty of Maryland’s Eastern Shore, the setting feels peaceful and relaxed—where quiet mornings and golden sunsets become part of everyday life.Inside, the home is designed for comfort and easy living, featuring a desirable first-floor primary suite that provides both privacy and convenience. The spacious family room, anchored by a cozy gas fireplace, creates the perfect gathering space, while the rear screened-in porch invites you to unwind and enjoy the tranquil surroundings. Upstairs, you’ll find two additional bedrooms along with a versatile bonus room—ideal as a home office, playroom, or craft space—plus walk-in attic storage for added functionality.Outdoor living shines with a brand new deck complete with a hot tub, perfect for relaxing or entertaining under the stars. An oversized two-car garage and ample parking accommodate your lifestyle with ease, including space for an RV, a boat, or both. Recent updates offer peace of mind, including a new roof (2024), HVAC system and hot water heater within the last five years, and the added benefit of a one-year Choice Home Warranty.Blending comfort, flexibility, and Eastern Shore charm, this home is a wonderful opportunity to enjoy a lifestyle that feels both relaxed and connected. Schedule your private tour and make this home yours.

Built in 2018, this custom coastal raised home is ideally located just one block from the Chesapeake Bay, offering the perfect blend of relaxation, recreation, and investment potential. Enjoy easy access to Rock Hall’s 12 marinas, Ferry Park Beach, local restaurants, shops, and charming downtown—all just a short walk, bike ride, or drive away. Nature lovers will appreciate the close proximity to Eastern Neck Island National Wildlife Refuge, where you can explore by foot, kayak, or bike.Designed for both everyday living and entertaining, the home features an oversized two-car garage with abundant parking—ideal for storing kayaks, paddleboards, bikes, jet skis, and more. The spacious, private backyard sets the stage for gatherings with a fire pit and over 1,000 square feet of wraparound decking invites you to take the party upstairs. A covered porch offers the perfect spot to relax and enjoy summer storms or gentle coastal breezes, and the outdoor shower makes rinsing off after a day on the Bay a breeze.Inside, you’ll find beautiful hardwood floors throughout, generously sized bedrooms, and a thoughtfully designed layout. The primary suite includes dual closets—one being an oversized walk-in—a full en-suite bath with tub/shower combo, and private deck access complete with a TRX workout area. The main living level showcases a bright, open-concept floor plan with stunning 360-degree views, ideal for entertaining. The top level features stainless steel appliances, granite countertops, and walls of windows that flood the space with natural light and capture glimpses of the Bay.Multiple sliding glass doors on every level seamlessly connect indoor and outdoor living, making the expansive decks a true extension of the home.Furnishing will be offered to be purchased making this turnkey, this property also boasts a proven rental history with three years of returning Airbnb and VRBO guests—providing excellent income potential for the weeks you’re not enjoying it yourself. Annual income details available upon request.Don’t miss this exceptional opportunity to own your slice of the Bay lifestyle!

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.

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!

Introducing 1213 Somerset Road—an exceptional opportunity to own a beautifully appointed residence in the heart of Severn, MD, where comfort meets elevated living.From the moment you arrive, this home exudes charm and sophistication, offering a thoughtfully designed layout enhanced by natural light and refined finishes throughout. Step inside to experience an inviting interior where spacious living areas create the perfect balance of elegance and functionality—ideal for both everyday living and stylish entertaining.The kitchen serves as the heart of the home, featuring generous cabinetry and workspace designed to inspire both casual meals and memorable gatherings. The bedrooms provide a serene retreat, offering ample space and comfort, while the living and dining areas flow seamlessly to create a warm yet upscale ambiance.Step outside to your private outdoor setting—an ideal canvas for creating your own backyard oasis. Whether hosting intimate gatherings or enjoying quiet moments, the outdoor space offers both versatility and tranquility.Perfectly positioned in a sought-after location, this home provides convenient access to major commuter routes, Fort Meade, shopping, dining, and entertainment—delivering both luxury and lifestyle.1213 Somerset Road is more than a home—it’s an opportunity to experience refined living in one of Anne Arundel County’s most convenient locations.

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.

Welcome home to refined coastal living on Maryland’s Eastern Shore in this beautifully designed 3-bedroom, 3-bath home located in the premier 55+ community of Bay Bridge Cove in Stevensville, Maryland.This lovely and well-maintained home was built in 2022 and offers 2,074 square feet over two levels. The home blends light-filled spaces with effortless, low-maintenance living just minutes from the Chesapeake Bay.Soaring cathedral ceilings elevate the main living area, where a propane fireplace creates a warm focal point for entertaining or just relaxing. The kitchen is designed for gathering, featuring granite countertops, a custom backsplash, stainless steel appliances, and an expansive center island with cabinetry on both sides — ideal for casual breakfasts or evenings entertaining friends and neighbors. A dining area is located between the kitchen and living area, completing the truly open concept. Enjoy your morning coffee or curl up and read a good book in the sunroom located just off the living room, featuring lovely views of the tree lined open space at the rear of the home — no neighbors behind you! The main-level primary suite offers tray ceilings, dual closets, double vanities, and a beautifully tiled walk-in shower — a peaceful retreat at day’s end. A second bedroom and full bath on the main level provide convenience for guests, while the upper level offers a private third bedroom with full bath and a spacious family room with custom railing overlook, perfect for extended stays or additional living space.Other features of the home include a welcoming gated courtyard with charming bistro lighting, perfect for a little gardening, or unwinding at the end of the day. Beautiful custom blinds are tailored to each room, ceiling fans are located throughout, and the front and rear storm doors provide even more light into this light and airy home. The two-car garage has ample space for your vehicles, water toys, or just some extra storage. The lawn irrigation system helps to maintain a plush lawn, and lawn maintenance is included in the HOA, allowing you to enjoy the community lifestyle Bay Bridge Cove residents embrace.Bay Bridge Cove residents settle into a vibrant, resort-style setting with an oversized clubhouse with fitness center, meeting and gathering spaces, full kitchen, community pool, pickleball, and bocce. Activities abound at this gathering spot all year round! The walking/biking trails are throughout the community, as well as a dog park for your furry family members, and even a community garden for those fresh summer vegetables.Ideally located just minutes from the Chesapeake Bay, area golf courses, waterfront dining, shopping, and multiple marinas. Annapolis is a short 15 minutes away, Washington DC is about an hour, and Atlantic Coast beaches are approximately a 2-hour drive. This home offers the perfect balance of coastal charm, convenience, and active adult living, and is just waiting for you to call this HOME! Schedule your private tour today!

Nestled in the shadows of the Choptank River is a meticulously maintained home in the water-privileged neighborhood of Asbury. Expansive lot sizes give you the privacy needed within a walkable neighborhood. Sit in your rocker with a cocktail while enjoying the dream turned into a reality of a wrap-around porch. A large rear screened-in porch to watch the local wildlife opens onto extensive hardscaping, perfect for an outdoor fire pit to enjoy those cool evenings with family and friends. Large open kitchen into the family room is the heart of the home that features a wood stove. 4 substantial bedrooms upstairs. Main floor features an office that could be a wide range of things, including a main floor bedroom. Steps from the Asbury Nature Trail that brings you to your community dock and water access with Huge views of the Choptank River.

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.

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.

Perfectly situated on over an acre, this custom-built masterpiece offers over 4,000 SF with three fully finished levels thoughtfully designed for luxurious living and effortless entertaining. From the moment you arrive, you'll appreciate the meticulous care, craftsmanship, and extensive upgrades this home has to offer. Step inside to find a spacious formal dining room framed by elegant segmental archways, setting a warm and inviting tone. The main level flows seamlessly into the heart of the home — the gourmet kitchen — featuring soft-close cabinetry, a large center island, dual ovens, under-cabinet lighting, an induction cooktop, a spacious walk-in pantry, and a reverse osmosis water filtration system connected to both the kitchen sink and refrigerator. Adjacent to the kitchen, a cozy breakfast nook provides the perfect space for everyday meals. The expansive family room offers the ideal gathering place, complete with a pellet stove, a beautiful wet bar perfect for entertaining, and oversized sliders that fill the space with natural light. These sliders open directly to the screened-in porch — newly updated with pet-resistant screens — and lead to an attached deck, creating even more space for outdoor relaxation. Upstairs, the second level is designed for ultimate comfort. The luxurious oversized primary suite features a private propane fireplace, dual walk-in closets, and a spa-like en-suite bathroom with a luxury stone jacuzzi tub, rainfall shower, abundant natural and overhead lighting, and separate his-and-hers vanities. Two additional bedrooms with spacious closets, a large bonus room with a pellet stove (ideal for a recreation room or optional sixth bedroom), and a second full bathroom complete this floor. For added convenience, a second-floor laundry room makes everyday living even easier. The third level offers two more versatile bedrooms, a full bathroom, and access to the HVAC system — perfect for home offices, guest suites, or teen retreats. The solar panels will be paid off before closing The outdoor space is just as impressive. Enjoy a partially fenced yard, ideal for children and pets to safely roam, an oversized attached 2-car garage with access to the crawl space, a detached 2-car garage that makes an excellent workshop, storage space, or man cave, plus an additional storage shed. A partial whole-house generator provides added peace of mind. And the best part? No HOA! Located just minutes from downtown Centreville's charming shops, restaurants, marina, and parks, with easy access to Route 301 and only 13 miles from the Bay Bridge, this property truly leaves no comfort feature overlooked. Welcome to a home where luxury, privacy, and convenience meet — your Eastern Shore dream awaits.

Discover 92.71 acres of unspoiled Eastern Shore beauty, offering a captivating blend of mature woods, marshland, and tranquil natural ponds that draw in abundant waterfowl. This property creates exceptional habitat for sika deer and other native wildlife—perfect for hunters, outdoor enthusiasts, or those seeking a private nature retreat. The wooded, firm terrain provides easy access throughout, while nearby public boat ramps offer quick entry to the Chesapeake Bay. A rare opportunity to own a serene and secluded slice of Maryland’s scenic countryside.

Unplug from the hustle and bustle in this well maintained one floor home on the banks of the Choptank River. The views of the native wetlands and its wildlife are unique and beautiful in a way only mother nature can create. The spacious and quiet yard receives abundant sunlight and could provide for amazing gardening opportunities. An old dock remains in need of extensive repair but the next owner could benefit from this water access and boating opportunity. The neighborhood itself is a huge plus with a public landing and direct access from within the neighborhood to the miles of trails in the Lynch Preserve, maintained by the Eastern Shore Land Conservancy. Indoor/outdoor living is a plus with the sunroom, deck, rear patio and gazebo for reflecting. A spacious living and dining room flows well with the kitchen and the laundry room behind provides great pantry space. The oversized 2 car garage has enough space for both cars and water toys. Properties like this are irreplaceable and can be a great way to invest in improving your quality of life.

Two parcels combine for a total of 5.22 acres, offering a rare blend of space, versatility, and opportunity. The separate 3.21-acre parcel is perc-approved and buildable, currently used for hunting, and includes its own right-of-way for private access. The main home sits on 2.012 acres and has been lovingly maintained and thoughtfully updated over the years.Inside, you’ll find a spacious and flexible layout featuring a stunning 24x24 great room—converted from the original attached garage—complete with a gas stove, central air, and seamless flow into the kitchen. Luxury vinyl plank flooring runs throughout much of the home, complemented by stainless steel appliances and numerous system upgrades, including newer windows, roof, well, and septic.Upstairs offers three bedrooms, including a primary suite with an updated bathroom featuring new flooring and vanity. The main level includes a large living room, formal dining area, and a bright kitchen, plus an enclosed sunroom with sliding glass doors that open to a fenced-in, in-ground 15x30 pool—perfect for entertaining or relaxing.The lower level adds even more functionality with an updated full bath, large laundry area, bonus room, and ample storage, along with a new French drain and sump pump system.Outbuildings are equally impressive, including a large shed with kennel and a substantial 36 X 48 pole barn with concrete floors, drain, heat, car lift, 12-foot doors storage in attic, and lean-to—ideal for hobbyists, contractors, or storage of equipment and recreational vehicles. A generator hookup is already in place for added peace of mind.Enjoy excellent hunting opportunities for turkey, deer, and geese, all while being just minutes from the Delaware line. This unique property offers endless possibilities for living, building, and outdoor recreation.Interior professional pictures to come!

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 35 foot deep water boat slip 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.

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 a brand new 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 with storage above, 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), all new first-floor 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!!

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.

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

Welcome to 5419 Ragged Point Road — Closer than you think to D.C., Baltimore, and Ocean City, a striking contemporary waterfront estate set on 11.88 private acres with an incredible 1,500 feet of frontage along serene Brooks Creek. Designed for those who appreciate the best of Eastern Shore living, this 4-bedroom, 2 full/3 half bath custom home, built in 2007, offers exceptional craftsmanship and luxury throughout with all the designer furnishings included.The gourmet kitchen is a chef’s dream, featuring marble countertops and top-tier appliances, including Wolf, Bosch, and Sub-Zero. The elegant primary suite offers a spa-like retreat with a soaking tub and separate shower. Expansive living spaces open to multiple balconies and decks, each perfectly positioned to capture breathtaking water views.Outdoor amenities include a private pier with approximately 3 feet MLW (mean low water), complete with water, electric, and a 12,000 lb boat lift — ideal for boating and fishing enthusiasts. For hunters, a duck blind on the property and abundant wildlife make this a rare hunting paradise.Whether you are savoring the sunrise over the creek, entertaining guests, or exploring the surrounding natural beauty, this extraordinary property delivers a lifestyle of unmatched tranquility and recreation.

Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office. Kitchen with marble countertops and a huge professional refrigerator. Fully finished basement. 2 car attached garage. The first outbuilding is a office space with 2 private offices, a conference room, a gym, kitchenette and half bath. The second outbuilding features 5 garage bays and a finished area that serves as a family room with kitchenette. This property is nothing short of spectacular.

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 readyIt 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 a master suite. Two sets of French doors open to either the front lawn or side yard for entertaining. The unique design of the conservatory also provides a near 180-degree view of the harbor and all of the sunrises and sunsets.With the lowest price per square foot for a Luxury, Waterview, in town home, it is also a comparatively excellent value.

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. Come and be amazed!!