Chestertown Homes with Swimming Pool Community Amenities

Welcome to Chestertown, Maryland – a hidden gem nestled in the heart of Kent County! Known for its rich history and charming waterfront, Chestertown offers a vibrant blend of small-town allure and modern conveniences. With its picturesque streets lined with historic buildings, delightful boutiques, and cozy cafés, this quaint town invites you to explore its unique character. The beautiful Chester River, with its scenic views and recreational opportunities, is just a stone’s throw away, making it a perfect backdrop for outdoor enthusiasts.

For those seeking a home that combines comfort and leisure, Chestertown boasts a selection of stunning properties featuring community amenities, including refreshing swimming pools. Imagine spending sun-soaked afternoons lounging poolside, surrounded by lush landscaping and the serene sounds of nature. These homes not only offer a private retreat but also foster a sense of community, where neighbors gather for summer barbecues or relaxing evenings by the water.

Chestertown is not just about beautiful homes; it’s about a lifestyle. Residents enjoy access to well-maintained parks, walking trails, and community events that celebrate local culture and heritage. The town’s commitment to preserving its historical charm while providing modern amenities ensures that you’ll feel right at home.

Whether you're looking to raise a family, retire in peace, or simply enjoy a slower pace of life, Chestertown is a perfect choice. Discover your dream home today in this enchanting town, where community spirit and natural beauty come together seamlessly. Your oasis awaits!

Newest Chestertown Homes with Swimming Pool Community Amenities

$839,500

3 Beds ⋅ 3 Baths

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large walk-in closet, and access to the private balcony. Two additional bedrooms share a full bathroom. the upstairs is complemented by a convenient second-floor laundry. Catch a glimpse of the Chester River from the front porch or upper covered balcony, the perfect place to enjoy morning coffee or evening cocktails. Enjoy the waterfront lifestyle of the sought-after Chester River Landing community. Deep water boat slips are available for lease or purchase. The community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! This home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

102 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$635,000

Buildable waterfront lot in the Chester River Landing community. This prime location captures panoramic views of the Chester River! Just steps away from deep water boat slips, which are available for lease or purchase. Perfect location to build your dream home on the water. The Chester River Landing community amenities include docks, in-ground pool, grilling and outdoor dining area right on the water, large firepit, a beach to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club. Enjoy the close proximity to ample shops, dining options, and Chestertown’s year-round farmers market.

108 Little Harbor Way, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

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