3 Bedroom 2 Bath homes for sale & real estate in Chestertown, MD

3 Bedroom 2 Bath Homes for Sale in Chestertown, MD

Welcome to 24204 Drayton Landing Drive — a beautifully renovated 3-bedroom, 2-bath home set on 2 peaceful acres in the heart of Kent County on Maryland’s Eastern Shore. Nestled within the desirable Kinnairds Point community, residents enjoy a warm neighborhood setting along with exclusive access to two waterfront common areas: a boat launch and a swim beach. These shared spaces provide the perfect opportunity to experience the Chesapeake Bay and the natural beauty of Still Pond Creek and Churn Creek. This single-story residence offers a spacious first-floor primary suite, an attached 2-car garage, a charming screened porch ideal for unwinding, plus a large composite deck and two

3 Bedroom 2 Bath Homes for Sale in Chestertown, MD

Tucked away along the quiet shores of Still Pond Creek, this cedar cabin offers a rare blend of privacy, comfort, and natural beauty. Surrounded by mature woods and set on a peaceful stretch of waterfront, this 1,944 square foot home features 3 bedrooms, 2 bathrooms, a spacious screened-in porch perfect for crab feasts, a private beach and pier with 2'+ MLW improved with bilk head installed by Army Corps. Whether you’re seeking a weekend retreat or a year-round escape, this property captures the essence of Eastern Shore living—simple, timeless, and immersed in nature where mind, body, and soul find balance.

3 Bedroom 2 Bath Homes for Sale in Chestertown, MD

Welcome to Silly Manor, a Chesapeake Bay-front property with an abundance of coastal charm and panoramic views. This home is perfectly situated on the coveted Lawton Avenue, one of Kent County's most sought-after neighborhoods. Enjoy stunning sunsets all year-round and direct access to the dynamic waters of the Chesapeake Bay. The open living and dining space offer spectacular views of the Chesapeake. The kitchen opens up to the patio and garden, and has a spacious island for entertaining. The home was designed with a first-floor primary suite, offering convenient (and hard-to-find) one-floor living. There are two additional bedrooms and a full bath on the second floor. Watch the boats glid

3 Bedroom 2 Bath Homes for Sale in Chestertown, MD

Don’t let this one pass you by! Great opportunity to live near the water. Two blocks to the boat ramp (Chester River). Built in 2021 it compares nicely to new construction. Meticulously kept and maintained. A beautiful rancher in the town of Crumpton on 0.46 acres. The front porch welcomes you to a well -designed open concept 3 BR, 2 full bathrooms home. Natural light illuminates the living space. There is no shortage of amenities: an updated, modern kitchen with SS appliances, under cabinet lighting, granite countertops, whole house sprinkler system. The laundry room adjoins the kitchen. Plenty of room for all your outdoor activities. Easy commute to Route 301, Chestertown, Middlet

3 Bedroom 2 Bath Homes for Sale in Chestertown, MD

Seller offering up to $5,000 in closing cost assistance with accepted offer. Welcome to 115 Cemetery Lane, a charming home nestled in the quiet and friendly community of Church Hill, MD. This inviting property features 3 bedrooms and 2 full bathrooms, offering comfortable single-level living with a thoughtful layout. Step inside to a bright, open-concept living area with large windows that fill the space with natural light. The kitchen boasts ample cabinetry, modern appliances, and plenty of counter space perfect for home-cooked meals or entertaining. The primary suite includes a private bath and generous closet space, while additional bedrooms are ideal for guests, a home office, or family

3 Bedroom 2 Bath Homes for Sale in Chestertown, MD

Nestled in the charming subdivision of Centerville, this exquisite Colonial-style residence offers a harmonious blend of elegance and comfort, perfect for those seeking a refined lifestyle. Built in 2013, this detached home boasts a generous 2,454 square feet of thoughtfully designed living space, ensuring ample room for relaxation and entertainment. As you step inside, you are greeted by a warm and inviting atmosphere. Natural light pours in through large windows, enhancing the inviting ambiance and showcasing the home's sophisticated design. The gourmet kitchen is a culinary enthusiast's dream, featuring high-end appliances and ample counter space, making meal preparation a delight. Wheth