Welcome to this beautifully crafted home in the water-oriented community of Great Oak Estates, just outside of Chestertown on Maryland’s Eastern Shore. Nestled in a peaceful setting that backs to woods alive with songbirds and butterflies, this high-quality residence offers an easy-flow floor plan designed for both lively gatherings and quiet private moments. A soaring two-story foyer greets guests and opens to the living room and family room, the latter featuring built-in cherry cabinets and a cozy propane fireplace. The formal dining room connects seamlessly to the kitchen and an additional casual dining space, making entertaining effortless. The kitchen showcases handmade cherry cabinetry and a brand-new refrigerator. Hardwood floors run throughout the main living areas, while brand-new carpeting softens every bedroom. On the main level, the primary suite includes its own bathroom, a walk-in closet, and plantation shutters. A second main-floor bedroom (ideal as a guest room or home office) shares convenient access to the hall bath. Completing the first floor are a large walk-in pantry and a laundry room outfitted with a brand-new washer and dryer. Upstairs you’ll find two additional spacious bedrooms, each with its own walk-in closet, plus a full bathroom. An oversized walk-in attic provides abundant storage or the perfect opportunity to create a bonus room or extra living space. Dual zone HVAC provides comfort from a newer lower level unit and an upper unit replaced in 2026. Complete roof replacement was completed in 2026 as well. A voluntary HOA opens the door to the amenities of Safe Harbor Great Oak Landing Marina—private beach area, pool, 9-hole golf course, and more. Simply walk or hop in a golf cart to reach the marina and enjoy all the water-oriented lifestyle this community has to offer. You’re also minutes from Rock Hall, with its additional marinas, charter boats, shopping, and restaurants. Less than 10 minutes away lies Chestertown and Washington College, along with more shopping, dining options, a hospital, and a wonderful Saturday morning Farmers Market, and much more. Whether you’re seeking a full-time residence or a relaxing Eastern Shore getaway, this home delivers quality craftsmanship, flexible living spaces, and convenient access to the best of Great Oak Estates and the surrounding area.

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.

Country elegance at its finest with this recently updated and spacious Cape Cod in the water oriented community of Clearview, just minutes from historic Chestertown. The amenities here are a major plus with Franklin pond and community access directly to Churn Creek. The home has had a transformation in the last 2 years with updated bathrooms, floors, kitchen, landscaping, and a new HVAC unit. The main floor master suite allows you to live in luxury with two walk in closets, hardwood double doors, and brand new bathroom with soaking tub and walk in steam shower. Upstairs is a blend of spacious bedrooms and bathrooms galore with an office nook to look out at nature. Storage is no issue with a full basement ready to take on as many holiday decorations as your heart desires. The property is sprawling on over 4 acres that abut the community pond and green space. Outdoor living is celebrated here with a massive deck out back for entertaining and covered front porch for birdwatching. The abundance of our Eastern Shore is just a short ride away with local staples such as Red Acres Hydroponics and Lockbriar Farms for your produce right in Worton and the Chestertown Farmer's Market for the rest. Invest wisely while improving your quality of life.

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.

Welcome to a breathtaking country estate where modern elegance, architectural grandeur, and total sanctuary converge across 2.23 serene acres. Spanning over 4,000 square feet of meticulously refined living space, this extraordinary five-bedroom residence has been thoughtfully crafted to offer both lavish entertaining possibilities and effortless multi-generational comfort.Upon arrival, the welcoming foyer makes a memorable first impression, framed by detailed custom millwork and flanked by a private executive office and a sophisticated study or formal dining space. Moving inward, the magnificent two-story great room commands attention with its soaring ceilings and a cozy gas fireplace crowned by a classic raised brick hearth. At the heart of the main level lies a gourmet kitchen designed for grand gatherings, showcasing fresh luxury vinyl flooring, select new appliances, and a stunning quartz-topped center island with a prep sink that easily reconfigures for multi-purpose hosting. Sunbeams flood the adjoining sunroom, creating a seamless transition to the outdoors while mirroring the warmth of the home’s main-floor primary suite. This private retreat features a spacious walk-in closet and a newly remodeled, spa-inspired bath complete with new quartz double vanities, sleek updated fixtures, a large walk-in shower, and an exquisite standalone soaking tub.Offering unmatched independence and comfort, a fully self-contained ground-level suite on the lowest level serves as the ultimate in-law or guest quarters. Complete with its own private ground-level entrance, open-concept kitchen and living area, dedicated laundry, and an accessible bath with a walk-in shower, this wing ensures total convenience without sacrificing style. A new addition to the lower level unlocks movie-theater magic with a fully furnished screening room ready for immediate enjoyment. Upstairs, four generously proportioned bedrooms accompany a beautifully refreshed hall bath.The exterior grounds are nothing short of a resort-style paradise. Step out onto the back porch to take in sweeping views of the lush landscape and expansive partially fenced yard. The sparkling inground pool serves as the crown jewel of the outdoor space, newly upgraded with all-new mechanicals including a dedicated heater. Surrounding the water, extensive custom hardscaping leads to a fireside gathering area, while an oversized gazebo with an outdoor fan offers a shady retreat on warm afternoons. With a brand-new roof installed in 2026, a newly resurfaced driveway, and space remaining for future additions, this estate represents a rare opportunity to experience sophisticated countryside living at its finest and, less than 5 minutes from Chestertown's restaurants, shopping, and Farmer's Market.Updates to the home are available in Documents

This over 5 acre waterfront estate on Churn Creek is a true Eastern Shore recreational property. Besides the home itself, the grounds include a board and batten cabin to serve as base camp for water sports down by the water, dock with direct access to the Chesapeake Bay, barn with a stall for your horse or sheep, and detached 2 car garage with lounge area above. Here you can enjoy the abundance and lifestyle of the Eastern Shore with crabbing, fishing, hunting, water skiing, sailing and hikes on the nature trail all available on site. Outdoor living is huge here with multiple spaces to connect with nature and enjoy the privacy of your own waterfront sanctuary. The home is the perfect size for a weekend getaway or full time residence with a floorplan that has been expanded and opened up to accommodate the amazing views and 2026 lifestyle. Storage is a breeze with a full basement including a shop and rec room for grandkids or guests to go enjoy with privacy. One floor living makes for an easy flow with the primary suite opening to a brick patio with sliders and including both an ensuite bathroom and walk in closet. The blend of amenities on site and proximity to Chestertown's Historic District make this the perfect magnet house to attract friends and family or an amazing investment opportunity.

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.

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.