Winchester is situated in the Litchfield Hills, north of Torrington, offering residents a superior quality of life with well-maintained public schools, industrial parks, lakes and numerous recreational activities. Winsted is the incorporated city within the town, close to where Route 8 intersects with Route 44.

The area downtown is undergoing a long-term revitalization to enhance its beauty and attract people to the several small shops. There will be a landscaped center median down Main Street, new sidewalks, gorgeous lighting, new signs and landscaping. Connecting Winsted with Torrington is the Still River Greenway, with 5-mile paths along the banks of the Still River, which will accommodate bicyclists, joggers and inline skaters.

Students attend one of two public elementary schools before graduating to the middle school. In 1895, William L Gilbert, a local businessman, found the Gilbert School, which now serves high school students from Winchester and close by Hartland. Supporting the school is a private endowment and public funds. Located in downtown Winsted is a two-year state college, Northwestern Connecticut Community College. Earning national recognition is the college's special assistance program for the deaf and hearing impaired.

As Winchester aggressively pursues new businesses for the Winchester Business Park, an active Economic Development Commission assists them. The Winsted Industrial Park is already home to several manufacturers who provide work for many residents.

Well known for its summer and year-round colonies of homes, Highland Lake provides many recreational activities. Highland Lake, 444-acres, attracts boaters, swimmers, water-skiers and anglers. Team sports and activities for each and every age and ability is coordinated by the active recreation department.