Chester Harbor Real Estate

Chester Harbor Real Estate

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 life, making it an ideal destination for families, retirees, and everyone in between.

Chester Harbor is characterized by its stunning views of the Chester River, where residents can enjoy breathtaking sunrises and sunsets from the comfort of their own homes. The area is renowned for its lush landscapes and well-maintained properties, creating a tranquil environment that invites relaxation and outdoor activities. Whether you’re an avid boater, fisherman, or simply love to stroll along the water’s edge, Chester Harbor provides the perfect backdrop for your lifestyle.

The subdivision boasts a strong sense of community, with friendly neighbors who often gather for seasonal events and local gatherings. Families will appreciate the proximity to top-rated schools, parks, and recreational facilities, ensuring that there’s always something to do. The nearby historic downtown Chestertown is brimming with charming shops, delightful eateries, and cultural attractions, making it easy to immerse yourself in the local culture.

Accessibility is another highlight of Chester Harbor. Located just a short drive from major highways, residents can easily explore the wider region, including Annapolis and the Eastern Shore’s beautiful beaches.

If you’re seeking a peaceful retreat with a strong community spirit, Chester Harbor is the perfect place to call home. Discover the beauty and charm of this delightful subdivision today!

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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Joseph Ciganek

As an Eastern Shore Realtor, I know that a real estate transaction is built on trust. I pride myself on my honesty and integrity in providing the highest quality representation for my clients. I have spent my entire life in Chestertown and on the Chesapeake Bay and have a deep respect and understanding for why life here is so special. You can rely on my deep knowledge of the eastern shore and its waterways when buying a home. As an Eastern Shore native, full-time Realtor and licensed Attorney, I have the skill set to help you navigate any real estate transaction; waterfront, farms, commercial, you name it. Buying or selling real estate requires an experienced and trustworthy advocate. Let me be your guide. Growing up on the banks of the Chester River, I was fortunate enough to enjoy everything the Chesapeake Bay has to offer, whether crabbing, fishing or just about every water-sport you can think of. After graduating from Washington College with a B.A. in Economics and Finance, I attended University of Baltimore School of Law. Working full time and going to school at night, I graduated cum laude and proceeded to clerk for the Honorable Harris P. Murphy, Circuit Court of Kent County, Md. That’s when I decided to make a drastic career shift to practicing full time as a Realtor in 2021. Since then I have enjoyed showing others why life on the shore really is the land of pleasant living. Outside of real estate, I enjoy getting exercise with my black lab, playing pickleball, soccer and racing the historic log canoe sail boats up and down the Chesapeake Bay.

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