Chester Harbor Homes with Asphalt Driveway Parking desc

Welcome to Chester Harbor, a picturesque subdivision nestled in the charming town of Chestertown, Maryland. Located in Queen Anne’s County, this serene community offers the perfect blend of tranquil living and vibrant local culture. Surrounded by lush landscapes and the gentle flow of the Chester River, Chester Harbor is an ideal destination for those seeking a peaceful retreat while still being close to the amenities of town.

The homes in Chester Harbor are designed with comfort and convenience in mind. Each residence features an inviting asphalt driveway, providing not only a sleek and polished look but also ample parking for you and your guests. Imagine returning home after a long day to your beautifully landscaped property, where the smooth asphalt leads you straight to your front door. These thoughtful design elements ensure that your home is not only functional but also a welcoming space for family and friends.

Living in Chester Harbor means embracing a lifestyle rich in outdoor activities and community spirit. Enjoy leisurely strolls along the river, explore nearby parks, or partake in local events that showcase the vibrant culture of Chestertown. With a close-knit community feel, Chester Harbor is more than just a place to live; it’s a place to thrive.

Whether you’re looking for your first home, a vacation getaway, or a peaceful place to retire, Chester Harbor has something for everyone. Come discover the charm and beauty of this delightful subdivision, where your dream home awaits!

Newest Chester Harbor Homes with Asphalt Driveway Parking desc

$349,000

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:

$320,000

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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