Chestertown Historic District Homes with Rear Yard Lot features

Welcome to the Chestertown Historic District, a captivating gem nestled in the heart of Kent County, Maryland. This charming area boasts a rich tapestry of history, where colonial architecture meets modern living, creating an inviting atmosphere that appeals to both history enthusiasts and contemporary homebuyers alike. As you stroll through the tree-lined streets, you’ll be enchanted by the well-preserved 18th and 19th-century homes, each telling its own story of the past.

The Chestertown Historic District is not just about the beautiful facades; it’s a vibrant community brimming with local shops, delightful eateries, and cultural attractions. The area is home to Washington College, which adds a youthful energy and a variety of events to the calendar year-round. Whether you’re enjoying a leisurely afternoon at the waterfront or participating in one of the many local festivals, there’s always something happening in this lively town.

For those seeking a home in this historic enclave, many properties feature spacious rear yard lots, providing a perfect canvas for gardening, entertaining, or simply enjoying the serene surroundings. Imagine hosting summer barbecues or quiet evenings under the stars in your own private outdoor oasis. With the charm of historic architecture combined with the modern comforts of spacious lots, homes in the Chestertown Historic District offer a unique opportunity to embrace a lifestyle that is both rich in heritage and brimming with possibilities.

Come explore the enchanting Chestertown Historic District, where history meets community, and find your dream home today!

Newest Chestertown Historic District Homes with Rear Yard Lot features

$419,999

4 Beds ⋅ 2 Baths

ALSO AVAILABLE FOR LEASE: Please reach out to agent for details. This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes an adorable kitchen with butcher block countertops, as well as a living room, dining room, and 3/4 bathroom. Upstairs, you’ll find three bedrooms, a full bath, and a walk-in closet. The third floor offers a lofted bedroom and bonus room - perfect for a playroom, office, or workout room. The mahogany-floored porch has interchangeable screens and windows, converting easily from a screen porch into a sunroom. Outside, a new six-foot pressure-treated pine fence provides privacy for the backyard, with an extra fenced garden area. The driveway has off-street parking for two vehicles. Additional home updates include a tankless hot water heater, high-efficiency 3-zone boiler, whole-house surge protector, upgraded panel, and Kenmore gas range. In summer 2025, the current owners invested in over $60,000 in major renovations hoping to stay for many years. They replaced the roof, updated the electrical wiring, and painted the interior. All upgrades were intended to be enjoyed by current homeowners. Unfortunately, they found that they had to move out of state to be closer to a new job.

222 Mount Vernon Ave, Chestertown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

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