Windham County occupies Vermont’s southeastern corner, bordering Massachusetts and New Hampshire. It’s one of the state’s oldest counties, chartered in 1781, and known for its vibrant arts, covered bridges, and serene rural landscapes. Brattleboro, the county seat, is a creative hub filled with galleries, bookstores, and farm-to-table cafés. Other towns such as Dover, Wilmington, and Newfane attract visitors for their historic architecture and ski resorts like Mount Snow. The region is mostly rural with pockets of small-town vibrancy. Homes range from renovated 1800s farmhouses and Victorian cottages to modern chalets in mountain resort zones. The Connecticut River forms the eastern boundary, offering scenic waterfront living for some communities. Average home prices hover around US $420,000. In Brattleboro and Newfane, buyers can find historic houses for US $300,000–450,000, while ski-country lodges or riverfront homes rise above US $650,000. New construction generally runs US $325,000–500,000 depending on the terrain. Boston lies about two and a half hours south, making Windham popular with out-of-state second-home owners.