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Downtown Chestertown Real Estate

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Downtown Chestertown Real Estate

Welcome to Downtown Chestertown, a charming and vibrant subdivision nestled in the heart of Maryland's picturesque Kent County. This quaint riverside town, rich in history and culture, offers an idyllic setting for those seeking a blend of small-town charm and modern amenities.

Downtown Chestertown is renowned for its beautifully preserved 18th-century architecture, lined with unique boutiques, art galleries, and delightful eateries that cater to a variety of tastes. Stroll along the serene waterfront, where you can enjoy stunning views of the Chester River, or take part in the lively community events that bring residents together throughout the year. From the annual Chestertown Tea Party Festival to the bustling Farmers Market, there’s always something happening in this close-knit community.

The area is also home to Washington College, which adds a youthful energy and a wealth of cultural opportunities, including lectures, performances, and art exhibitions. Nature enthusiasts will appreciate the abundance of outdoor activities, with nearby parks and trails that invite exploration.

With its friendly atmosphere, rich history, and vibrant community spirit, Downtown Chestertown is more than just a place to live; it’s a lifestyle. Whether you’re looking for a cozy historic home or a modern townhouse, this subdivision offers diverse real estate options to suit your needs. Experience the charm and warmth of Downtown Chestertown, where every day feels like a getaway, and make it your new home today!

Newest Listings in Downtown Chestertown

108 N Water St, Chestertown image
108 N Water St, Chestertown $1,125,000

This 1925 classic colonial, three story residence, with both front and back gardens, is uniquely situated in the center of the favored 100 block of North Water Street, in...

  • 5 Beds
  • 4 Baths
Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact:

200 High St, Chestertown image
200 High St, Chestertown $2,300,000

A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and s...

Courtesy of Taylor Properties

Listing courtesy of Taylor Properties. Contact:

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Century 21 Gold Key Realty
600 Peoples Plaza Newark Delaware 19702
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