Tolchester Homes with Wooded Lot Description

Tolchester Homes with Wooded Lot Description

Welcome to Tolchester, an enchanting subdivision nestled in the heart of Chestertown, Maryland, within the picturesque Kent County. This charming community offers a unique blend of serene living and natural beauty, making it the perfect place to call home.

Tolchester is renowned for its tranquil setting, characterized by homes that are thoughtfully situated on wooded lots. Imagine waking up each morning to the soothing sounds of nature, with the rustle of leaves and the songs of birds as your backdrop. These wooded lots not only provide a sense of privacy and seclusion but also create a picturesque environment that enhances the beauty of your home. Whether you're sipping coffee on your deck or enjoying an evening stroll, the lush greenery surrounding you offers a peaceful retreat from the hustle and bustle of everyday life.

The homes in Tolchester are designed to harmonize with the natural landscape, featuring spacious layouts that invite an abundance of natural light. With a variety of architectural styles, each residence boasts unique charm and character, ensuring that you’ll find a home that perfectly suits your lifestyle.

Additionally, Tolchester is conveniently located near the historic downtown Chestertown, where you can explore quaint shops, delightful dining options, and vibrant community events. With easy access to outdoor activities along the Chester River and nearby parks, this subdivision truly embodies the best of Maryland living.

Discover the beauty and tranquility of Tolchester, where your dream home awaits amidst the enchanting woods. Come experience the perfect blend of comfort, nature, and community!

Newest Tolchester Homes with Wooded Lot Description

8796 Maryland Pkwy, Chestertown
$1,495,000
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:

8796 Maryland Pkwy, Chestertown
$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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