Chestertown Historic District Homes for Sale

Welcome to the Chestertown Historic District, a charming enclave nestled in the heart of Kent County, Maryland. This picturesque area is renowned for its rich history, stunning architecture, and vibrant community spirit. Established in the 18th century, Chestertown boasts beautifully preserved colonial buildings that reflect its storied past, making it a delightful place to call home.

As you stroll through the tree-lined streets, you'll be captivated by the unique character of each residence. From stately Federal-style homes to quaint Victorian cottages, the Chestertown Historic District offers a diverse array of architectural styles that cater to various tastes. Each property tells a story, inviting you to become part of its legacy.

Currently, there are a number of homes for sale in this enchanting district, providing an excellent opportunity for those looking to invest in a piece of history. Whether you're searching for a cozy retreat or a grand family home, you'll find options that fit your needs and lifestyle. Many of these homes feature modern amenities while retaining their historic charm, offering the perfect blend of comfort and character.

Living in the Chestertown Historic District means embracing a vibrant community with access to local shops, restaurants, and cultural events. The nearby Chester River offers opportunities for boating and fishing, while the town's rich arts scene includes galleries, theaters, and festivals throughout the year.

Don't miss your chance to be part of this extraordinary community. Explore the homes for sale in the Chestertown Historic District and discover the perfect place to create lasting memories. Your dream home awaits!

Newest Chestertown Historic District Homes for Sale

$315,000

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:

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