Chestertown Homes with Swimming Pool Amenities

Welcome to Chestertown, Maryland—a charming gem nestled in the heart of Kent County. This picturesque town, with its rich history and vibrant community, offers an enchanting blend of small-town charm and modern amenities. Located along the scenic Chester River, Chestertown is known for its beautifully preserved 18th-century architecture, bustling arts scene, and a warm, welcoming atmosphere. Whether you're strolling along the historic streets, enjoying a riverside picnic, or exploring local boutiques and eateries, there's always something to discover in this delightful town.

For those seeking a home that embodies relaxation and leisure, Chestertown boasts a selection of properties with swimming pool amenities. Imagine soaking up the sun in your own backyard oasis, where you can unwind after a long day or entertain friends and family during warm summer evenings. Homes with swimming pools in Chestertown not only provide a refreshing escape but also enhance your lifestyle, offering a perfect setting for gatherings, barbecues, or simply enjoying a peaceful afternoon by the water.

Chestertown's real estate market is diverse, catering to a variety of tastes and budgets. From charming historic homes to modern builds, you're sure to find a property that suits your needs. The community is also known for its excellent schools, vibrant cultural events, and proximity to the stunning Chesapeake Bay, making it an ideal place for families, retirees, and anyone looking to embrace the best of Maryland living.

Explore the wonderful opportunities that await you in Chestertown, where your dream home with a swimming pool is just a heartbeat away!

Newest Chestertown Homes with Swimming Pool 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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