Chestertown, MD Homes for Sale with Acreage

80 private acres beautifully situated on the highly prized Langford Creek, this light filled custom built home and property capture the essence of serene living on Maryland's Eastern Shore. One of only 4 properties on Orchard Point and sited to take advantage of the natural landscape with expansive views of the river, the owners' goal was to retain the feel and function of a working farm, but to

Stacy Kendall

This waterfront farmette is a rare find just a few minutes from downtown Chestertown and features extensive updating. The new kitchen, 2 new full bathrooms, and new roof all from 2024 just to name a few have you set up for many years to come. Most of the property is cleared and grassy making it perfect for your equestrian retreat on the water. A detached 2 car garage is perfect for vehicles or

Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

$20,000 Price Reduction!A One-of-a-Kind Historic Treasure Reimagined for Modern LivingStep into history with this extraordinary Greek Revival chapel, originally built in 1865 as Walton Chapel and later renamed Mowbray Chapel. Nestled on 3.22 picturesque acres in Chestertown’s serene Quaker Neck community, this stunning brick structure has been thoughtfully restored and modernized, seamlessly

Jonathan Taylor Hyatt & Company Real Estate, LLC

Rare lake front property in Kent County! Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and

Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

Located in Country Club Estates, on a lovely, corner lot with mature trees. Solid brick rancher with good bones. 3 bedrooms, 2 full baths. The basement has a workshop space and garage. Hardwood floors. Spacious family room with woodstove. Nice screened-in porch and outdoor patio with a fire pit. Home is ready for your finishing touches. Near the Chester River Yacht and Country Club and just a

Peter Heller Coldwell Banker Chesapeake Real Estate Company

Located in the small Eastern Shore town of Fairlee, this spacious Bi-level sits on 1.65 acres of cleared land, just a short 10-minute drive to both Chestertown and Rock Hall. The home offers 3 bedrooms and 2 bathrooms, with a finished lower level for additional living space. A large sunroom with cathedral ceilings and walls of windows is the heart of the home, filling the space with natural

Robin Fithian Rock Hall Properties Real Estate

Minutes from the heart of Chestertown and a short drive to Rock Hall, this 2-bedroom, 1-bath home offers the perfect balance of small-town convenience and peaceful countryside living. Inside, you’ll find warm hardwood floors and an unfinished basement—ideal for storage, a home gym, or even your future office space. Outside, the large, level yard provides plenty of room to garden, play, or simply

Courtney Chipouras TTR Sotheby's International Realty

Serene 2-acre partially cleared wooded lot with existing 1900-built home, in need of major repair or possible tear-down. Value is in the land. No interior access – partial roof and floor collapse. Sellers accept no liability and are held harmless.Property includes well and septic (buyer to verify), detached building and shed. Close to water and surrounded by peace and privacy. Sold

Nicole Stephens Tesla Realty Group, LLC

Hartwell Estate features 80 private acres with pristine, panoramic views on the mouth of the Langford and Chester River. This light filled custom built home and property captures the essence of serene living on Maryland's Eastern Shore. One of only 4 premiere properties at the end of Quaker Neck, often called "Kent County's Gold Coast" is sited to take advantage of the natural landscape with

Richard Keaveney Cross Street Realtors LLC