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Chestertown Historic District Homes for Sale

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Chestertown Historic District Homes for Sale

Welcome to the Chestertown Historic District, a charming slice of Maryland that beautifully marries the past with the present. Nestled along the picturesque banks of the Chester River in Kent County, this vibrant community is steeped in rich history and offers a unique lifestyle that is hard to resist. With its cobblestone streets, colonial architecture, and lush green parks, the Chestertown Historic District is a haven for those who appreciate the beauty of historic homes and a close-knit community atmosphere.

As you explore this enchanting neighborhood, you’ll discover a variety of homes for sale, each boasting its own unique character and charm. From beautifully restored Federal-style homes to quaint cottages that echo the town's storied past, there’s something for everyone in this picturesque district. Many of these residences feature stunning period details, such as original hardwood floors, intricate moldings, and inviting front porches that beckon you to sit and enjoy the serene surroundings.

Living in the Chestertown Historic District means you’re not just buying a home; you’re investing in a lifestyle. Enjoy leisurely strolls along tree-lined streets, vibrant local shops, and delightful eateries that showcase the best of Maryland’s culinary scene. With the annual Chestertown Tea Party and other community events, there’s always something happening to keep you engaged and connected with your neighbors.

If you’re looking for a home that offers both historical significance and modern conveniences, the Chestertown Historic District awaits you. Discover your dream home today in this captivating community where history and charm come together seamlessly!

Newest Chestertown Historic District Homes for Sale

111 Kent St S, Chestertown image
111 Kent St S, Chestertown $450,000

Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this ...

  • 2 Beds
  • 3 Baths
Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

212 Washington Ave, Chestertown image
212 Washington Ave, Chestertown $675,000

This charming American Four Square has been meticulously maintained and is located 1 block from Washington College’s campus and near Chestertown’s Historic District’s sho...

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

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

105 High St, Chestertown image
105 High St, Chestertown $1,195,000 ▼

Morning light pours through restored original windows. The river shimmers a block away, and a mansard roof that has watched over High Street since 1863 frames it all. Reb...

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

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

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Century 21 Gold Key Realty
600 Peoples Plaza Newark Delaware 19702
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