Chester is a town in Middlesex County, Connecticut, United States. The population was 3,743 at the 2000 census. The town center is also defined by the U.S. Census Bureau as a census-designated place (CDP). According to the United States Census Bureau, the town has a total area of 16.8 square miles (44km2), of which, 16.0 square miles (41km2) of it is land and 0.8 square miles (2.1km2) of it (4.75%) is water. The CDP has a total area of 2.1 square miles (5.4km2) of which 1.46% is water.