Waterfront homes for sale & real estate in Chestertown, MD

Waterfront Home for sale in Chestertown, MD:

Waterfront living on Grays Inn Creek, just five minutes from Rock Hall. Situated on a private half-acre lot with protected western-facing views, this home offers beautiful sunsets, 3–4 feet MLW, and easy boating access to the Chester River, Chestertown, Kent Narrows, and Rock Hall. The home has seen numerous updates over the past six years, including new siding, roof, HVAC, LVP flooring, carpet, an updated kitchen and main-level bathroom, appliances, and improvements to the pier. Water views take center stage from the dining area, living room, and main bedrooms, while the manageable size and low-maintenance updates make this an easy waterfront property to enjoy. The property offers pl

Waterfront Home for sale in Chestertown, MD:

Waterfront Living at the Head of Still Pond Creek Well-maintained and beautifully situated, this 3-bedroom, 3-bath waterfront home offers a peaceful setting at the head of Still Pond Creek. Enjoy the best of Eastern Shore living with serene water views, a quiet natural backdrop, and easy access to the Chesapeake bay. Conveniently located with very easy access to Chestertown and points north, this property is ideal as a full-time residence, weekend retreat, or waterfront getaway. A rare opportunity to enjoy comfort, convenience, and the charm of life on Still Pond Creek.

Waterfront Home for sale in Chestertown, MD:

Discover the best of waterfront living in the sought-after community of Kinnairds Point. Set on 3.5 acres in a private, peaceful setting and thoughtfully designed for both everyday comfort and effortless entertaining, this home provides generous space for guests while maintaining inviting living areas that feel equally welcoming when it is just a few people, approximate square footage is close to 3,000. It is the best of both worlds: room to gather, comfortable spaces to unwind, and an exceptional waterfront setting. This home provides five bedrooms with an additional enclosed sleeping loft attached to one of the bedrooms, three and a half bathrooms, renovated kitchen and bathrooms, fi

Waterfront Home for sale in Chestertown, MD:

Beautiful waterfront on nearly 7 acres. Spacious composite deck overlooking Still Pond Creek. Private dock with 3 ft MLW (buyer to verify). Large living room with gleaming hardwood floors and huge sliders looking onto the deck and Still Pond Creek. 2 woodburning fireplaces. Updated kitchen with high-end stainless steel appliances. Laundry room off the kitchen. Steps down to your private waterfront oasis and dock. The lower level features a large family room, 2 bedrooms, a full bath and plenty of storage. This home has that unmistakable Eastern Shore feel. You won't want to miss this spectacular property.

Waterfront Home for sale in Chestertown, MD:

A truly special Eastern Shore property! This charming Tidewater Cape is beautifully positioned on the point of 13.78 acres, surrounded by the tidal waters of the Chester River. Built in 1950 by a father and son as a summer retreat, the home has been loved and enjoyed by generations and is filled with character and timeless charm. The setting begins to reveal itself as you travel the wooded drive and catch glimpses of the river through the trees. As you approach the homesite, the trees open and water appears on both sides, showcasing the property's unique point setting, privacy, and natural beauty. Charming and inviting from the front, the home's true presence is best appreciated from the wa

Waterfront Home for sale in Chestertown, MD:

Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend r