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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

24607 Chestertown Rd, Chestertown image
24607 Chestertown Rd, Chestertown $365,000

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 ...

  • 3 Beds
  • 3 Baths
Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

300 And 302 S Mill St, Chestertown image
300 And 302 S Mill St, Chestertown $1,195,000

Remarkable 1 acre downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homes...

  • 2 Beds
  • 1 Baths
Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

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:

201 N Lynchburg St, Chestertown image
201 N Lynchburg St, Chestertown $695,000 ▼

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:

201 N Lynchburg St, Chestertown image
201 N Lynchburg St, Chestertown $695,000 ▼

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:

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

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...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact:

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 12/4/2026, 10:00 AM. Bidding ends 12/8/2026, 1:30 PM. The l...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact:

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

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: $...

Courtesy of Ashland Auction Group LLC

Listing courtesy of Ashland Auction Group LLC. Contact:

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Century 21 Gold Key Realty
600 Peoples Plaza Newark Delaware 19702
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