The Middlefield Green is a grassy expanse of about 1.12 acres in Middlefield Center at the intersection of Center Street (Jackson Hill Road) and Main Street. Town Hall Road, which is really a service road providing access to the fire station north of the green, is the northern boundary. The green is comprised of two distinct levels. At the southern point of the triangle is a flat grassy spot. From that point, the land gradually rises up 6-10 feet to another plateau at the most northerly edge.

There is an assortment of deciduous trees (sugar maple, Norway maple, sweet gum and crabapple and one large blue spruce), some forming a line along Jackson Hill Road and Main Street. At the most southerly corner near the spruce is a small perennial garden surrounded by a stone retaining wall. On the highest plateau is a flag pole surrounded by three war memorials. Bronze plaques on the granite bases commemorate those who fought in World War I, World War II and Vietnam. Clipped yew bushes are interspersed with the monuments. Slightly to the south at the crest of the rise is a bell from the second Congregational Church that commemorates the site. Across Town Hill Road near the eastern corner is a large stone with a brass plaque commemorating the site of the Old Town Hall that stood on the site until 1964.

Surrounding the green is a collection of residential, civic and religious structures. Most of the 20th century structures are located to the north of the green. This includes the fire station across Town Hall Road (1937, 1867) and the Middlefield Middle School, set back from the green and separated from the fire station by a large asphalt parking lot. The town hall, another 20th century structure, is situated across Jackson Hill Road north of the green. Its impact is minimal because of its distance from the green.

Primarily 19th century structures line Jackson Hill Road and Main Street. This includes residences dating from the 19th century and two churches, the Federated Church (1862) and the Episcopal Church (1866); which has been converted to a library. While their historic presence is definitely felt, the green is dominated by the presence of the larger-scaled, newer structures of utilitarian design at the top of the knoll overlooking the green.

The Town of Middlefield has a long-term lease from the owners, the Middlefield Congregational Church, now the Middlefield Federated Church. Proposed changes to the green must first be approved by the church. The town maintains the green with the exception of the perennial planter area, which is maintained by the local Garden Club.