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Chestertown Real Estate

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Chestertown Real Estate

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!

Newest Listings in Chestertown

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown image
201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown $300,000

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...

Courtesy of RE/MAX Associates-Hockessin

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

Tonopah Rd, Chestertown image
Tonopah Rd, Chestertown $3,000

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 1:00 PM. The l...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

201 N Lynchburg St, Chestertown image
201 N Lynchburg St, Chestertown $750,000 ▼

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...

Courtesy of RE/MAX Associates-Hockessin

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

201 N Lynchburg St, Chestertown image
201 N Lynchburg St, Chestertown $750,000 ▼

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

  • 2 Baths
Courtesy of RE/MAX Associates-Hockessin

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

Towhee Rd, Chestertown image
Towhee Rd, Chestertown $5,000 ▼

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:40 PM. The ...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

Beltram Rd, Chestertown image
Beltram Rd, Chestertown $5,000 ▼

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:25 PM. The ...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

Fish Hatchery Rd, Chestertown image
Fish Hatchery Rd, Chestertown $5,000 ▼

ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:35 PM. The ...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124

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