The Cheshire Green, located within a National Register Historic District, is semicircular in shape and bounded by Church Drive on the west and Route 10 on the east. Route 10 is Cheshire's main street and is a heavily traveled thoroughfare. Mature trees randomly planted throughout provide shade for the flat, evenly graded greensward. Near the northern tip is a lone shade tree. A sidewalk runs along Route 10 and another perpendicular to it leading across the green to the stately church. A single monument, a simple stone Civil War obelisk (1866) commemorating Cheshire veterans, is located near the northern portion of the green.

Ranged around the curvilinear side of the green are white clapboarded buildings that relate to it historically, functionally and visually. The church designed by David Hoadley, a respected Connecticut architect, is the centerpiece. To the south of it is the latest building facing the green, The Reverend Van Voight Parsonage, built in 1912 (on the site once stood a tavern, a hotel and, later, trolley barns). The dwellings to the north of the church date from the early-19th to the late-19th centuries. Immediately to the north and south of the green are additional buildings that relate to the historical evolution of the town center but face Route 10 rather than the green. These include the Abijah Beach Tavern (c. 1750) to the south and Rufus Hitchcock Store (1787/1947) and the Methodist Church (1840/1970); now Temple Beth David) to the north.

The red brick Town Hall (1867) across Route 10 is a major presence in the town center. Like both churches, it has had later additions that reflect the changes in the community over time. In front of it is a newly landscaped area that includes a modern sculpture; a large brick war memorial honoring the veterans of all American wars; and an earlier World War One monument consisting of a boulder with a bronze plaque. Detracting from the historic town center is the modern bank and drive-up teller machine to the north of the Town Hall directly across from the green.