The Madison Green is roughly rectangular in shape with a triangular wing to the west. It is located within a National Register Historic District and just west of the commercial district. It is bordered by the Boston Post Road on the south; Meeting House Lane on the east and north; and Copse Road on the west. Mostly mature trees are planted around the perimeter but not enough to block its view from the street. The 3.44 acre greensward appears larger than it is because of the open expanse to the north of Meeting House Lane that forms the lawn and drive of the First Congregational Church (1838). Sited on a slight rise, the imposing Greek Revival structure is the focal point of the green and can be seen from almost anywhere on or around it.

Two parallel asphalt paths not far from each other cross the center of the green and lead to a tree-lined drive leading to the church on the other side of Meeting House Lane. Another asphalt path crosses from east to west just south of the center of the green. Paths also cut diagonally across the north corners.

Most of the trees are planted around the edge of the green at uneven intervals. There tend to be more at the corners. In the center where the paths cross are three large trees, a small leafed European linden and two elms. Most of the trees are labeled according to species. There are several varieties of oak and maple trees and some large Norway spruce trees. In the southeast corner where the green is extended into the parking lot are three war memorials and several rows of young ornamental trees planted to screen a portion of the parking lot from the green.

The memorials are arranged around a cruciform-shaped gravel bed with plantings. They include a large boulder with a bronze plaque honoring veterans who fought in World War One; a large grey cut stone with a bronze plaque remembering those who fought in World War Two, Korea and Vietnam; and a smaller boulder with a bronze plaque remembering the Revolutionary War (1991). A flagpole is located in the center.

The smaller triangular portion of the green to the west at the corner of Britton Lane and the Boston Post Road is rimmed with trees of various species. In the center is a flagpole. At the western tip is a boulder with a bronze plaque erected in 1968 commemorating Thomas Chittenden, a Madison native who became the first governor of Vermont.

The green is surrounded by civic, religious and residential structures. To the east on the other side of the parking lot is a cluster of civic buildings including Memorial Hall, now the Town Hall (1896); a community meeting building (c. 1884); Academy Elementary School (1884); and Lee Academy (1821). The fact that the green was the focus of religious activity and remains such is evident by the presence of the Congregational Church and the recently constructed Lutheran Church (1955 & 1969).

Across from the green along the Boston Post Road is a row of 18th and 19th century houses. The oldest house in Madison, the Grave House (1685), is just east of the green. Houses built in the 20th century are located to the west along Copse Road and Britton Lane.