Chestertown Homes with Boat Ramp Community Amenities

Welcome to Chestertown, Maryland, a picturesque gem nestled in the heart of Kent County. This charming town, steeped in history and rich in culture, offers a unique blend of small-town warmth and vibrant community life. With its scenic waterfront along the Chester River, Chestertown is a haven for outdoor enthusiasts and those who appreciate the beauty of nature. Stroll along the historic streets lined with 18th-century buildings, explore local art galleries, or indulge in the delightful eateries that showcase the region's culinary talents.

For those who love the water, Chestertown is home to several communities with exclusive boat ramp access, making it easy to enjoy the serene waters of the Chester River. Imagine waking up to the gentle sounds of nature and having your boat ready for a day of fishing, kayaking, or sailing right at your doorstep. These homes not only provide direct access to the water but also foster a sense of camaraderie among neighbors who share a passion for the great outdoors.

The boat ramp community amenities enhance the lifestyle in Chestertown, offering residents the perfect balance of relaxation and adventure. Whether you’re hosting a summer barbecue by the water or embarking on a spontaneous sunset cruise, living in this vibrant community means embracing a life filled with unforgettable experiences. With its charming atmosphere and abundant recreational opportunities, Chestertown is more than just a place to live—it's a place to thrive. Come explore the possibilities that await you in this enchanting town!

Newest Chestertown Homes with Boat Ramp Community Amenities

$269,000

3 Beds ⋅ 2 Baths

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$1,375,000

4 Beds ⋅ 5 Baths

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway. Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom. The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement. This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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