The Westbrook Green is roughly triangular in shape containing .65 acre and bordered by Route 1 on the south. Route 153 splits into two one-way streets on the north and forms both the eastern and western boundaries. It is the focal point of the community and the civic center, but because there is little cohesive pattern to the buildings around it, its importance as a historic landscape is not as apparent as it might be.

The Town Hall, built in the Colonial Revival style, is on the south side of Route 1, just west of the green. Across from the street is the Congregational Church (1894), built on the site of the first meetinghouse, on a ridge that slopes away from the green toward the west. It is situated across from the green but oriented toward Route 1. The Old Burying Ground is directly west of the church across the street. Route 1 is a busy commercial strip and while some attempts have been made to design new commercial buildings across from the green in keeping with its historic character, the attempts fall short.

The green itself is shaded by a few trees, the mature ones mostly planted around the border along Westbrook Place and Essex Road. It is dominated by the old public library building (c. 1905) erected near the eastern corner. In that same corner is the "Honor Roll," a boulder with a bronze eagle mounted on top and four large bronze plaques, one on the face of the stone and the other at its base. It is dedicated to all those from Westbrook who fought in World Wars I and II, Korea and Vietnam. The veterans' names are listed. Near the memorial is a flagpole. In the western-most corner is a flower bed, a stone watering trough, and the town historical marker.

The streetscape has been seriously compromised. With the exception of a building in the Greek Revival style that has been converted to commercial use, the buildings along Route 1 facing the green are contemporary, one-story commercial buildings that allow plenty of space for parking, so a good portion of the lot is covered by asphalt. Along the eastern border is an early 20th century commercial block that shows signs of deterioration. This is unfortunate because the buildings share party walls and are evenly set back from the street and, as such, help maintain the street line and provide scale for the green. The remaining buildings are primarily residential. Some have been converted to commercial use and suffer from unsympathetic alterations. As a result, the buildings around the green tend to detract from rather than enhance its historic and cultural significance.