The Academy Hill Green is a long triangle, its sides bounded by Academy Hill Road and Clark Street, and its point just where they intersect with each other and with Derby Avenue, a short distance south of the Derby/Ansonia town line. Mansfield Street defines its base. Sloping steeply up (southward) from Derby Avenue, the character of the green is residential, quiet, and rather deserted. From the top of the green, there are views to the northwest; some of the plantings and furnishings are arranged to take advantage of the views rather than to enhance the character of the green itself. Although Derby Avenue is heavily traveled, the elevation of the green reduces the traffic noise to a distant roar.

All the buildings facing the green are houses or small outbuildings related to houses. The oldest is a Greek Revival house with some later 19th-century additions located opposite the southeast corner of the green, at the intersection of Clark and Mansfield Streets. North of it on Clark street and southwest of it on Mansfield Street are two very large Queen Anne houses, with porches and towers or turrets. Both stand on large lots, partly hidden by overgrown shrubbery, and both look slightly run-down. On Academy Hill Road is a row of five smaller houses, beginning diagonally opposite the green, at the intersection of Academy Hill and Mansfield Street. Two of these seem to have been built around the turn of the century, one is a bungalow, and two are early-to-mid-20th century Colonial Revival. Two more Greek Revival houses flank the green at its northern point; both of them face outward onto Derby Avenue and turn their backs to the green. The green is curbed along Academy Hill Road. The other edges are rough; parking is possible on the edge of the green along Mansfield Street only. Telephone poles and wires run along both long sides of the green; at one point a wire stretches from one side to the other across the green.

Trees and furnishings are dotted irregularly across the green, some of them oriented toward the view and others with perhaps their own internal logic, or perhaps no logic at all. Mature trees include a cluster of willow trees at the southwest corner, a looser cluster of maples across the mid-section, and two large, multi-trunked trees at the northern point. In addition, there are numerous small ornamental trees (perhaps dogwoods or cherries), fairly recently planted, a large evergreen, a small pine, and a very large clump of forsythia.

A swingset stands near the southeastern corner. There are two benches: one about halfway down the Clark Street side, sited to the view; and one at the bottom of the hill, near the point. At the center of the green stands a large memorial consisting of a U-shaped granite curb, three short unmarked granite stones (looking like gravestones cut off by a lawnmower) and one tall stone saying, "Ye Ancient Common of the Founders of Derby, 1684-1904, Erected by Daughters of Founders and Patriots of America." Flanking and behind this memorial stand three cedar trees. At the northernmost point of the green (nearest Derby Avenue) stands the Connecticut Historical Commission Bicentennial sign for Derby; and about twenty feet uphill from it is a horse trough of polished granite with a plaque reading, "1906 -Presented by the National Humane Alliance, Herman Lee Ensign, Founder." Overall maintenance seems adequate.