Chestertown Historic District Homes with Traditional Style

Welcome to the enchanting Chestertown Historic District, a charming enclave nestled in the heart of Kent County, Maryland. This picturesque area is steeped in rich history and offers a unique blend of traditional architecture and modern amenities, making it an ideal destination for homebuyers seeking a vibrant community with character.

The Chestertown Historic District is renowned for its stunning collection of traditional-style homes, each telling a story of the past while seamlessly integrating into the present. As you stroll through the tree-lined streets, you'll be captivated by the exquisite craftsmanship displayed in the colonial and federal-style residences, many of which date back to the 18th and 19th centuries. These homes feature classic elements such as elegant brick facades, charming porches, and intricate woodwork, providing a timeless appeal that resonates with history enthusiasts and families alike.

Living in the Chestertown Historic District means embracing a lifestyle rich in culture and community. Residents enjoy easy access to local shops, art galleries, and delightful eateries that showcase the best of Maryland's culinary offerings. The nearby Chester River invites outdoor enthusiasts to partake in boating, fishing, and leisurely walks along its scenic shores.

In addition to its historical significance, the district is home to various community events and festivals that foster a strong sense of belonging among residents. Whether it's a summer concert in the park or a winter holiday celebration, there's always something happening in this vibrant neighborhood.

Discover the charm of the Chestertown Historic District, where traditional homes and a close-knit community await you. Come and be a part of a living history that continues to thrive!

Newest Chestertown Historic District Homes with Traditional Style

$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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