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. Situated in the heart of Queen Anne’s County, this charming subdivision offers a unique blend of serene living and vibrant community life. With its stunning waterfront views and lush landscapes, Chester Harbor is the perfect escape for those seeking tranquility without sacrificing convenience.

The homes for sale in Chester Harbor are as diverse as the residents who call this delightful neighborhood home. From cozy single-family residences to spacious modern designs, there’s something to suit every taste and lifestyle. Many properties boast beautiful outdoor spaces, ideal for entertaining or simply enjoying the natural beauty that surrounds you. Imagine sipping your morning coffee on a sun-drenched patio or hosting summer barbecues in your backyard oasis.

Living in Chester Harbor means embracing a lifestyle filled with outdoor adventures. The nearby Chester River offers opportunities for boating, fishing, and kayaking, while the surrounding area is perfect for hiking and biking enthusiasts. Plus, the historic charm of Chestertown is just a stone’s throw away, featuring boutique shops, delightful eateries, and a vibrant arts scene.

As you explore the homes for sale in Chester Harbor, you’ll discover not just a house, but a place to create lasting memories. Whether you’re a first-time buyer or looking to downsize, this welcoming subdivision has everything you need to make your dream home a reality. Come experience the magic of Chester Harbor—where community spirit meets the beauty of nature!

Newest Chester Harbor Homes for Sale

4 Beds ⋅ 2 Baths

Extra-wide fenced lot, and just minutes from Chestertown and Chester Harbor. Introducing this spacious 4-bedroom, 2-bath ranch on an extra-wide fenced lot in Chester Harbor, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan that's move-in ready with the opportunity to add your own cosmetic updates. The generous layout includes four bedrooms, two full baths, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard provides plenty of room for gardening, entertaining, pets, or future expansion. Enjoy your morning coffee or evening unwind on the side porch, while the attached one-car garage adds convenient storage. As part of the Chester Harbor community, you'll enjoy access to the community boat ramp and the Chester River, making it easy to spend your days boating, fishing, kayaking, or simply enjoying the waterfront lifestyle. Ideally located near marinas, parks, waterfront dining, and the charm of downtown Chestertown, this property offers the perfect blend of space, convenience, and recreational opportunities.

533 Round Top Rd, Chestertown

Listing courtesy of EXP Realty, LLC. Contact: 8333357433

3 Beds ⋅ 2 Baths

COMING SOON!! Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced yard and a paved driveway. The roof, siding, and windows were replaced approximately 10 years ago, offering added value and peace of mind. Stay warm and keep utility costs down during the colder months with both a pellet stove in the living room and a wood-burning stove in the basement. With just a little updating, this home could be everything you've been looking for. Offering privacy, space, and endless potential, it's a great opportunity to make it your own. Located just minutes from the historic waterfront town of Chestertown, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and plenty of ways to experience the scenic beauty of the Chester River. The area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore.

240 Round Top Rd, Chestertown

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183

3 Beds ⋅ 2 Baths

Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

109 Parma Rd, Chestertown

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

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 ⋅ 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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