Tolchester Homes for Sale

Tolchester Homes for Sale

Welcome to Tolchester, a hidden gem nestled in the picturesque town of Chestertown, Maryland. Known for its serene atmosphere and charming community, Tolchester offers a unique blend of natural beauty and modern living, making it the perfect place to call home. This delightful subdivision is set against the backdrop of the stunning Chesapeake Bay, providing residents with breathtaking views and a plethora of outdoor activities.

Tolchester boasts a variety of homes for sale, catering to diverse tastes and lifestyles. Whether you're seeking a cozy cottage, a spacious family home, or a waterfront property, you'll find an array of options that reflect the area's rich character. Each home is designed with comfort and style in mind, featuring modern amenities while preserving the timeless charm that Chestertown is known for.

Living in Tolchester means embracing a lifestyle filled with community spirit and outdoor adventure. Residents enjoy easy access to local parks, walking trails, and the bay, perfect for boating, fishing, and leisurely strolls along the water. The nearby historic Chestertown offers a vibrant arts scene, delightful shops, and a variety of dining options that showcase the region's culinary delights.

As you explore the homes for sale in Tolchester, you'll discover not just a property, but a welcoming community where neighbors become friends and memories are made. Experience the tranquility and charm of Tolchester, where your dream home awaits amidst the beauty of Kent County, Maryland. Come and see why so many are choosing to call this enchanting subdivision their home!

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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