South Green, about 1.72 acres, is a horseshoe-shaped parcel with a rectangular-shaped wing at the southwest corner. Located at the southern end of Main Street, it is a focal point of the important artery and defines the south end of Middletown's commercial district. Situated within a National Register Historic District, it is bounded by Main Street on the north and Pleasant Street on the east. South Main, Church and Broad Streets meet to form the southern border. What used to be part of Church Street is now a dead-end street providing access to the adjacent buildings. Parking for the green forms the western boundary.

The green is flat with a gradual slope from east to west. Mature deciduous trees provide a dense canopy over most of the site. The trees include a very stately copper beech at the west corner and two old crabapple trees at the westerly end. Toward the eastern edge is a line of sycamore trees in tree wells along Main Street. Other deciduous trees are scattered along the edge of the green, including oaks, lindens, maples, and a willow. Only two non-deciduous trees are found on the green; a new blue spruce and a stately Norway spruce.

Concrete paths encircle the green and radiate inwards in a curvilinear fashion from each of the four corners to meet at the center. There they encircle a Civil War Monument designed in 1874 by M.H. Mossman consisting of a granite monument faced with bronze plaques containing the soldiers' honor roll. It is surrounded by four cannons. To the south of the Civil War memorial is a bronze bust of Henry Clay Work mounted on a boulder and flanked by the two old crabapple trees. Work was a prominent composer who lived in Middletown. Along Main Street is a flagpole and a Memorial Fountain (1909). The green is well lit by street lights along the perimeter.

The triangular-shaped wing was added in the 1970s, closing off Church Street to the north. A sidewalk was added following its western boundary, trees were planted and site amenities were added.

While the core of the green retains much of its 19th century character, the streetscape around it has evolved substantially to include 18th, 19th and 20th century buildings that serve residential, commercial, civic and religious purposes. This variety is inviting but efforts should be made to resist further development such as the Middletown Press building across Main Street from the green. Such building encourages increases in the size of the lot, thereby increasing the size of the building on that lot, which would significantly change the character of the streetscape.