Chester Harbor Homes for Sale

Chester Harbor Homes for Sale

Welcome to Chester Harbor, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers a unique blend of serene waterfront living and vibrant community spirit, making it the perfect place to call home. Located in Queen Anne's County, Chester Harbor boasts stunning views of the Chester River, providing residents with a tranquil escape from the hustle and bustle of everyday life.

The homes for sale in Chester Harbor are as diverse as they are inviting. From cozy cottages to spacious family residences, each property is thoughtfully designed to complement the natural beauty of the area. Many homes feature expansive decks and patios that invite outdoor living, perfect for entertaining guests or simply enjoying the breathtaking sunsets over the water. Inside, you'll find modern amenities paired with classic charm, ensuring that every home offers both comfort and style.

Life in Chester Harbor is enhanced by a strong sense of community. Residents enjoy access to nearby parks, walking trails, and recreational activities, making it easy to embrace an active lifestyle. The quaint downtown area of Chestertown is just a short drive away, offering boutique shopping, delightful dining options, and a rich cultural scene.

Whether you're looking for a peaceful retreat or a vibrant community to grow in, Chester Harbor has something for everyone. Explore the homes for sale today and discover the perfect blend of waterfront living and small-town charm that awaits you in this enchanting subdivision. Your dream home in Chester Harbor is just a heartbeat away!

Newest Chester Harbor Homes for Sale

$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:

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