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Chestertown Historic District Real Estate

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Chestertown Historic District Real Estate

Welcome to the Chestertown Historic District, a captivating blend of charming architecture and rich history nestled in the heart of Kent County, Maryland. This picturesque subdivision is a true gem, offering a unique glimpse into the past while providing modern amenities for today’s discerning homeowners.

The Chestertown Historic District is renowned for its beautifully preserved 18th and 19th-century buildings, showcasing a variety of architectural styles, including Federal, Georgian, and Victorian. Strolling through the tree-lined streets, you'll be enchanted by the vibrant facades, intricate details, and the warm sense of community that defines this area. Many homes boast original features such as hardwood floors, crown molding, and spacious porches that invite you to relax and enjoy the serene surroundings.

Located along the banks of the Chester River, the district not only offers stunning waterfront views but also a plethora of recreational activities. Residents can enjoy kayaking, sailing, and fishing, or simply take a leisurely walk along the scenic waterfront parks. The area is also home to a vibrant arts scene, with galleries, theaters, and cultural events that celebrate local talent and history.

Chestertown's historic charm is complemented by its convenient access to modern amenities. With boutique shops, delightful cafes, and fine dining options just a stone's throw away, everything you need is within reach. Plus, the district is in proximity to top-rated schools and healthcare facilities, making it an ideal place for families and retirees alike.

Experience the allure of the Chestertown Historic District, where history meets community, and every day feels like a step back in time. Come discover your dream home in this enchanting neighborhood!

Newest Listings in Chestertown Historic District

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:

105 N Water St Unit 3, Chestertown image
105 N Water St Unit 3, Chestertown $459,000 ▼

Second story, waterfront condo in historic Chestertown. Comes with a private boat slip at the end of the dock. 2 bedrooms and 2 full baths. Spacious patio with a stunnin...

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

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. 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:

226 S Water St, Chestertown image
226 S Water St, Chestertown $898,000

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner ...

  • 3 Beds
  • 4 Baths
Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. 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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