Tolchester Homes with Colonial Style

Tolchester Homes with Colonial Style

Welcome to Tolchester, a charming subdivision nestled in the heart of Chestertown, Maryland, within picturesque Kent County. This delightful community is not just a place to live; it’s a lifestyle that embraces the rich history and natural beauty of the Eastern Shore. With its proximity to the Chester River and a vibrant downtown area, Tolchester offers both tranquility and convenience, making it a perfect retreat for families and professionals alike.

The homes in Tolchester are a stunning representation of Colonial architecture, characterized by their timeless elegance and traditional charm. Each residence boasts classic features such as symmetrical facades, gabled roofs, and inviting front porches that beckon friends and family to gather. The spacious interiors are designed with functionality in mind, often featuring hardwood floors, large windows that flood the rooms with natural light, and cozy fireplaces that create a warm ambiance for those chilly Maryland winters.

Living in Tolchester means you are just moments away from a wealth of recreational activities. Whether you enjoy boating, fishing, or simply taking leisurely strolls along the river, the scenic surroundings provide endless opportunities for outdoor adventures. Additionally, the historic charm of Chestertown offers unique shops, delightful eateries, and cultural events that bring the community together.

Embrace the elegance of Colonial-style living in Tolchester, where every home tells a story and every day feels like a getaway. Discover your dream home in this idyllic subdivision and experience the perfect blend of history, community, and natural beauty.

Newest Tolchester Homes with Colonial Style

$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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