Winchester is nestled in the southwest corner of Cheshire County on the Massachusetts line. With a population of approximately 4500 residents is rich in history, has a gorgeous landscape and an amazing sense of community. Winchester was originally settled in 1733 and incorporated in 1753. The town has a total area of 55.5 square miles of which 54.9 square miles is land and 0.6 square miles is water. There is 64 miles of roads. We consider Winchester a "small Town" with plenty to offer.

Governed by Elected Selectmen, Winchester supports the Winchester Elementary & Middle School. High school students attend Keene High School in Keene NH. Many of our resident’s volunteer to serve on various community organizations, Town boards, Town committees and commissions.

Winchester is a caring community, accepting people of all ages, backgrounds and economic means. Winchester remain a rural community connected to its agricultural heritage and supportive of sustainable farming. There are several recreational areas throughout the Town: Ellen Lambert Murphy Memorial Community Center, Pisgah State Park, Gardner Mt., Forest Lake, Ashuelot River and the Rail Trail. Winchester provides many opportunities for both summer and winter recreation offering a variety of outdoor activities; hiking, swimming, fishing, biking, snowmobiling, boating, 4-wheeling and much more.

Winchester also offers shopping, food, gas, lodging, medical clinic, racetracks, distillery, dining etc. Quiet living is what makes the Town of Winchester a special place to live and visit.