Chestertown Historic District Homes for Sale

Chestertown Historic District Homes for Sale

Welcome to the enchanting Chestertown Historic District, a hidden gem nestled in the heart of Kent County, Maryland. This charming area is renowned for its rich history, picturesque streets, and vibrant community spirit. Established in the 18th century, Chestertown boasts beautifully preserved architecture that tells the story of its colonial past, making it a delightful place for history enthusiasts and modern-day homeowners alike.

As you stroll through the tree-lined streets, you’ll encounter an array of stunning homes, each with its own unique character. From stately Federal-style houses to quaint Victorian cottages, the Chestertown Historic District offers a diverse selection of properties that cater to various tastes and lifestyles. Many of these homes feature original details such as hardwood floors, decorative moldings, and inviting porches, providing a perfect blend of historic charm and contemporary comfort.

For those looking to invest in this charming community, there are homes for sale that present an incredible opportunity to become part of the Chestertown legacy. Picture yourself living just steps away from the beautiful Chester River, where you can enjoy leisurely walks, boating, and vibrant local festivals. The district is also home to delightful shops, art galleries, and restaurants that showcase the best of local culture and cuisine.

With its stunning scenery, rich historical significance, and a warm, welcoming community, the Chestertown Historic District is more than just a place to live; it’s a lifestyle. Come explore the homes for sale in this captivating neighborhood and discover the perfect blend of history and modern living. Your dream home awaits!

Newest Chestertown Historic District Homes for Sale

$350,000
2 Beds ⋅ 3 Baths
✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic home. Nestled in the heart of downtown Chestertown, this property is filled with the original architectural details and timeless charm that historic home lovers dream about. Featuring 2 spacious bedrooms with the potential for a 3rd, 3 full bathrooms, a welcoming kitchen with an eat-in area, and a generously sized dining room, this home offers a solid foundation for restoration and reimagining. While the property is in need of some repairs and renovation, it presents an incredible opportunity for the buyer who has always dreamed of owning a piece of history; or the savvy investor looking for their next restoration project. Outside, escape to your own private backyard sanctuary complete with a brick patio, fountain, and peaceful garden setting, an unexpected retreat right in town. Please note that the home is currently furnished and filled with décor and personal property. All furniture, décor, and contents currently in the home will be auctioned prior to settlement and are not included in the sale unless otherwise agreed upon. If you've been waiting for the right historic home to make your own, this is your chance to bring new life to a true Chestertown treasure. 🏡✨

522 High St, Chestertown

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$1,245,500
5 Beds ⋅ 5 Baths
Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new systems, and refined living spaces. Just one block to the waterfront promenade or to morning coffee at Evergrain, the location captures the rhythm of Chestertown living—laid back yet polished, historic yet vibrant. This is more than a home; it is an irreplaceable asset and a true legacy property within one of Maryland’s most beloved waterfront towns.

105 High St, Chestertown

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

$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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