Chestertown, MD Homes for Sale under $1,500,000

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, one of the first British Royal Ports of Entry to the Americas. Completely restored in 2025 by one of the Eastern Shore’s iconic builders, the home blends historic character with modern comfort through thoughtful updates, new

Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away.The home features 4 bedrooms and 5 full

Ashton Kelley Gunther-McClary Real Estate

Price improvement! Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room

Peter Heller Coldwell Banker Chesapeake Real Estate Company

**To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

Julia Hilfiker Gunther-McClary Real Estate