Chestertown Homes for Sale

Chestertown Homes for Sale

Welcome to Chestertown, Maryland—a charming riverside town that beautifully blends historical charm with modern living. Nestled along the banks of the Chester River, Chestertown is known for its picturesque streets lined with 18th-century architecture, vibrant local arts scene, and a rich tapestry of cultural heritage. This quaint community offers a serene escape from the hustle and bustle of city life while providing easy access to urban conveniences.

Chestertown is not just a feast for the eyes; it’s also a place where community thrives. The town hosts numerous events throughout the year, including the renowned Chestertown Tea Party Festival and the annual Arts in the Park. With a strong sense of community and a welcoming atmosphere, residents often come together to celebrate the unique spirit of their town.

For those looking to make Chestertown their home, the real estate market offers a diverse range of properties to suit various lifestyles. From charming historic homes that echo the town’s rich past to modern single-family residences and cozy townhomes, there is something for everyone. Homes for sale in Chestertown often feature spacious yards, beautiful gardens, and proximity to the scenic waterfront, making it an ideal choice for families, retirees, and anyone seeking a peaceful retreat.

Explore the possibilities of calling Chestertown home, where every day feels like a vacation, and the beauty of nature is just outside your door. Whether you’re drawn by the historical allure, the vibrant community, or the stunning landscapes, Chestertown is ready to welcome you with open arms.

Newest Chestertown Homes for Sale

$675,000
5 Beds ⋅ 3 Baths
Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor living. Complete with a 2-car garage.

212 Washington Ave, Chestertown

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

$1,195,000
2 Beds ⋅ 1 Baths
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

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

$750,000
2 Baths
Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

201 N Lynchburg St, Chestertown

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