Welcome to Chestertown, a hidden gem nestled in the heart of Kent County, Maryland. This charming subdivision offers a unique blend of small-town allure and rich historical significance, making it an ideal place to call home. Known for its picturesque waterfront and vibrant arts scene, Chestertown boasts beautifully preserved architecture that tells the story of its colonial past.
As you stroll through the tree-lined streets, you’ll discover an array of local shops, cozy cafes, and delightful eateries that reflect the warm, welcoming spirit of the community. The town's proximity to the Chester River provides ample opportunities for outdoor enthusiasts, whether you’re kayaking, fishing, or simply enjoying a leisurely walk along the scenic waterfront.
Chestertown is also home to Washington College, which infuses the area with youthful energy and a variety of cultural events throughout the year. From art galleries to theater productions, there’s always something happening to engage residents and visitors alike.
Families will appreciate the excellent schools and community-oriented atmosphere that Chestertown fosters. The subdivision is characterized by spacious lots and friendly neighbors, creating a safe and nurturing environment for children to grow and thrive.
With its blend of history, culture, and community spirit, Chestertown offers a lifestyle that is both enriching and peaceful. Whether you’re looking to plant roots or enjoy a weekend getaway, Chestertown invites you to experience its charm and make it your own. Discover your dream home in this enchanting subdivision today!
Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country ...
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homes...
Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:
4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be s...
Listing courtesy of RE/MAX Associates-Hockessin. Contact:
Located in an area that has the potential for dense project of affordable homes. There are 6 lots total. 4 are vacant and a church sits on the other two. Lots of differen...
Listing courtesy of RE/MAX Associates-Hockessin. Contact:
Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.
Listing courtesy of RE/MAX Associates-Hockessin. Contact:
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:40 PM. The l...
Listing courtesy of Ashland Auction Group LLC. Contact:
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:30 PM. The l...
Listing courtesy of Ashland Auction Group LLC. Contact:
ONLINE AUCTION: Bidding begins 10/23/2026, 10:00 AM. Bidding ends 10/27/2026, 12:30 PM. This auction takes place on the Ashland Auction Group bidding platform. Deposit: $...
Listing courtesy of Ashland Auction Group LLC. Contact: