Chester Harbor Real Estate

Chester Harbor Real Estate

Welcome to Chester Harbor, a hidden gem nestled in the charming town of Chestertown, Maryland. This picturesque subdivision offers a serene escape from the hustle and bustle of city life while providing easy access to the vibrant community and natural beauty that Queen Anne's County has to offer.

Chester Harbor is characterized by its stunning waterfront properties, where residents can enjoy breathtaking views of the Chester River. The community is designed with a focus on outdoor living, featuring beautifully landscaped gardens, walking paths, and access to private docks for boating enthusiasts. Imagine waking up to the gentle sounds of nature and sipping your morning coffee while watching the sunrise over the water.

The subdivision is perfect for families, retirees, or anyone seeking a peaceful lifestyle. With a strong sense of community, Chester Harbor hosts various neighborhood events that foster connections among residents. The local amenities include nearby parks, recreational facilities, and a selection of quaint shops and restaurants in downtown Chestertown, where you can savor the local cuisine and explore unique boutiques.

Chester Harbor also boasts proximity to some of Maryland's finest attractions. Whether you’re interested in exploring historic sites, indulging in outdoor adventures, or enjoying cultural events, this location has something for everyone. With its perfect blend of tranquility and community spirit, Chester Harbor is not just a place to live—it's a lifestyle waiting to be embraced. Come discover your dream home in this idyllic subdivision and experience the charm of Chestertown firsthand!

Newest Listings in Chester Harbor

3 Beds ⋅ 2 Baths

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of Chestertown, yet tucked within the highly sought-after Queen Anne’s County School District, this beautifully updated 3-bedroom, 2-bath home is ready to impress. Step inside to find a spacious, open feel highlighted by a massive living room—perfect for gathering, relaxing, and entertaining. The heart of the home is the stunning, renovated kitchen, offering plenty of space to cook, host, and make everyday living feel a little more special. Both bathrooms have been tastefully updated, giving the home a fresh, modern feel throughout. Enjoy the ease of all one-level living, along with a screened-in porch that’s perfect for morning coffee, evening unwinding, or hosting friends without the bugs. Outside, you’ll love the great yard—ideal for play, pets, or simply enjoying the peaceful setting. Need extra space? The large detached 2-car garage offers plenty of room for vehicles, storage, hobbies, or a workshop setup. This water-oriented community offers private access to the Chester River just a couple of blocks away—perfect for kayaking, fishing, or soaking in those Eastern Shore sunsets. There’s also a voluntary property owners association at just $30/year if you’d like to participate. If you’ve been looking for space, updates, and that relaxed Eastern Shore lifestyle—all in a convenient location—this one checks all the boxes!

123 Heath Rd, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

3 Beds ⋅ 1 Baths

An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbing stairs, everything is located on one floor. the interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The bathroom has been tastefully refreshed, the home has been freshly painted with LPV flooring and carpet throughout. This home offers the ultimate in conveniences local public and private golf courses outlets Close Proximity to the Chester River, fine dining and easy access to major highways. Don't miss out on the chance to create your dream space in this prime Chestertown location! NEW HVAC SYSTEM TO BE INSTALLED

517 Round Top Rd, Chestertown

Listing courtesy of Keller Williams Flagship. Contact:

3 Beds ⋅ 2 Baths

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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