Chester Harbor Real Estate

Chester Harbor Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Chester_Harbor and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

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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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