Winchester is a town in Litchfield County, Connecticut, United States. The population was 11,242 at the 2010 census. The City of Winsted is located in Winchester.

Winchester was incorporated in 1771, and named after Winchester, in England.

According to the United States Census Bureau, the town has a total area of 33.8 square miles (88 km²), of which, 32.3 square miles (84 km²) of it is land and 1.6 square miles (4.1 km²) of it (4.61%) is water.

As of the census of 2000, there were 10,664 people, 4,371 households, and 2,849 families residing in the town. The population density was 330.4 people per square mile (127.6/km²). There were 4,922 housing units at an average density of 152.5 per square mile (58.9/km²). The racial makeup of the town was 94.44% White, 1.24% African American, 0.23% Native American, 0.93% Asian, 0.01% Pacific Islander, 1.69% from other races, and 1.46% from two or more races. Hispanic or Latino of any race were 3.17% of the population.

There were 4,371 households out of which 28.3% had children under the age of 18 living with them, 50.3% were married couples living together, 10.2% had a female householder with no husband present, and 34.8% were non-families. 28.0% of all households were made up of individuals and 11.9% had someone living alone who was 65 years of age or older. The average household size was 2.42 and the average family size was 2.97.

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