Tolchester Homes for Sale

Tolchester Homes for Sale

Welcome to Tolchester, a hidden gem nestled in the picturesque town of Chestertown, Maryland. This charming subdivision offers a unique blend of serene living and vibrant community spirit, making it an ideal destination for families, retirees, and everyone in between. Located in Kent County, Tolchester is just a stone’s throw away from the scenic Chester River, providing residents with breathtaking views and ample opportunities for outdoor activities such as boating, fishing, and hiking.

Tolchester boasts a variety of homes for sale, each designed to cater to diverse tastes and lifestyles. From cozy cottages to spacious family residences, the architectural styles reflect the rich history of the area while incorporating modern comforts. Many of these homes feature expansive yards, perfect for gardening or enjoying summer barbecues with friends and family. The community is known for its friendly atmosphere, where neighbors become friends and children play freely in safe, open spaces.

Living in Tolchester means you’re also part of a vibrant local culture. Chestertown is renowned for its historic charm, with quaint shops, delicious eateries, and engaging community events. The nearby Washington College adds a youthful energy to the area, offering art exhibits, lectures, and performances throughout the year.

If you’re searching for a place that combines the tranquility of nature with the warmth of a close-knit community, look no further than Tolchester. Explore the homes for sale today and discover the perfect setting for your next chapter. Your dream home awaits in this idyllic Maryland enclave!

Newest Tolchester Homes for Sale

$1,495,000
9 Beds 7 Baths
Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates. The grounds unfold past champion and organic fruit trees, a generous herb garden, an original 18th-century smoke house, two private bridges over Stoneybrook Pond which are all framed by woods and rolling farm fields. Inside, nine bedrooms and six-and-a-half bathrooms reveal nearly two and a half centuries of craftsmanship: original wood floors, brick floors in the dining room and kitchen, signature Bulls Eye moldings, exposed hand hewn beams, eight fireplaces and soaring 11-foot ceilings. For more than 40 years the property has operated as a successful Bed & Breakfast. An optional furniture package is available for a seamless turnkey transition. Its origins as a single-family residence also make it an extraordinary private estate, full-time home or weekend retreat. A coveted sewer allotment is included with the sale which opens the door for a future carriage house, barn, additional dwelling, stable, studio or expanded hospitality use. A new roof, a complete exterior paint job, new hot water heater, new well pump and updated electrical service were completed in 2025–2026. This delivers the rare combination of historic character and modern peace of mind. Tolchester Marina and the Shanty Beach Bar are a mile away. Rock Hall is six miles down the road and the charming historic district of Chestertown is just ten miles away. After nearly four decades of careful stewardship, the current owners are ready to pass on the privilege and the story of The Mitchell House.

8796 Maryland Pkwy, Chestertown

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

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