Tolchester Homes for Sale

Tolchester Homes for Sale

Welcome to Tolchester, a hidden gem nestled in the heart of Kent County, Maryland, just a stone's throw from the charming town of Chestertown. This picturesque subdivision is a perfect blend of serene living and community spirit, making it an ideal destination for families, retirees, and anyone in search of a peaceful retreat.

Tolchester boasts a variety of homes for sale, each with its own unique charm and character. From cozy single-family residences to spacious modern homes, there’s something here for everyone. Many of these properties feature stunning waterfront views, lush gardens, and ample outdoor space, perfect for entertaining or simply enjoying the natural beauty that surrounds you. With easy access to the Chesapeake Bay, residents can indulge in a plethora of water activities, including boating, fishing, and kayaking.

The community’s location offers the perfect balance of tranquility and convenience. Just minutes away, Chestertown presents a vibrant downtown area filled with boutique shops, delightful eateries, and rich historical sites. Enjoy the local farmers' market, art galleries, and seasonal festivals that bring the community together.

Families will appreciate the proximity to highly-rated schools and recreational facilities, ensuring that children have access to quality education and play. With a friendly neighborhood atmosphere and a strong sense of community, Tolchester is more than just a place to live; it’s a place to thrive.

If you’re searching for a home that encapsulates both comfort and lifestyle, explore the homes for sale in Tolchester today. Your dream home awaits in this idyllic Maryland community!

Newest Tolchester Homes for Sale

$1,650,000
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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