The Woodstock Common is an irregular-shaped parcel made up of three triangular lots that together comprise about 4.75 acres. They are bounded by roads on all sides. The main highway, Route 169, borders the western side of the longest triangle. The other roads include Childs Hill Road, Old Hill Road, Academy Road and Cemetery Hill Road. Because of its size, shape and terrain, it cannot all be seen at once.

The land slopes up to the east and north where the Woodstock Academy Classroom Building (1873) is impressively sited overlooking that portion of the common at the corner of Academy and Cemetery Hill Road. To the north of it is the rest of the campus consisting of six other structures including the Bracken Library (1924).

At the corner of Cemetery Hill Road and Route 169 across from the southernmost tip of the green is the Woodstock Congregational Church (1821) constructed in the Greek Revival style. It is sited facing the road and as such does not relate directly to the common. However, when viewing it from the south on the rise near the Academy, it and the cemetery behind it comprise a classic New England scene. At the other end of the common along Childs Hill Road is another church, the Evangelical Covenant Church. A post office is located across from the common along Route 169 at the northwest corner.

The remainder of the buildings around the green are residences dating primarily from the 19th century. The exception is the Woodstock Tavern across from the common along the northern portion of Academy Road behind a stone fence. The most important residence is Roseland Cottage, a delightful Gothic wood frame structure painted a bright pink with maroon and dark green details. It is impressively sited on a large lot set back from Route 169 behind a fence with granite posts spanned in wood with a quatrafoil motif. To the north of Roseland Cottage is another residence behind a substantial stone fence which lines up with the Roseland fence. Together, the fences provide the enclosure for the common along Route 169. Otherwise, its large size, irregular shape and sloping terrain, along with the large and numerous trees disallow any one building from dominating it or providing a sense of enclosure around it.

It is randomly planted with many healthy, large deciduous trees including sugar maple, ash, English oak, beech, white oak and a few hemlock trees. Other than the trees and two war memorials - bronze plaques on two large boulders that include all the major U.S. wars - the common remains relatively unimproved. No curbs protect it from the street and no paths direct circulation. The Woodbury Common and its streetscape appear very much as they did in the late 19th century.