The Chester Green is located on a plateau at the midpoint of a steep and rocky slope at the intersection of Goosehill Road and Liberty Street. The second meetinghouse, built in 1793 and substantially altered, is located at the northern end overlooking the triangulated green of about one acre. To the east is a steep wooded hillside with an outcropping of rock. To the south are two old cemeteries, one on either side of the intersection. The contrast of the serene grassy open space against the rocky outcropping and the old gravestones gives the historic green a dramatic air. To the west across Liberty Street is a residential neighborhood that developed about the time the second meetinghouse was being used by the congregation (with the exception of a c. 1960 ranch house located across from the western tip).

The green itself slopes from the southwest to the northeast. It is mostly open with trees planted along the edge including a combination of mature sugar maple trees (some of the oldest appearing to be about 100 years old) and smaller saplings and flowering dogwood. The smallest crabapple saplings along Goosehill Road are a result of a 1986 Arbor Day service. A sycamore tree was planted in 1990 to commemorate the activities of Mr. And Mrs. Edmund Delaney, both past-presidents of the Chester Historical Society. Shrub plantings were installed in 1972. A white wood gazebo situated at the tip of the intersection is the secondary focus of the green. It was placed there by the Rotary Club in the early 1980s. Surrounding it is a dense planting of evergreens, junipers, rhododendrons and arborvitae in formal clipped patterns. These and two teak benches were placed on the green in memory of Judy Joslow in 1981.

Parking is accommodated by a gravel lot behind the meetinghouse, which is lit by two lighting standards. To the southwest is an asphalt parking lot for the physically challenged. Both lots are connected to the meetinghouse by paths that circle around it and form an oval space in front where a flagpole is located.