Centered at the junction of Atkins Street and Country Club Road, the district encompasses a collection of well-preserved 18th and 19th-century architecture, including some of Middletown's oldest surviving buildings.

Four of the houses date from the mid- to late 18th century and were the homes of some of the earliest settlers in this part of Middletown.

These are typical Georgian style houses, wood-frame structure with large central chimneys.

[2]: 9 The Highland area was settled in the early 18th century by members of the Warner, Wilcox, and Bacon families.

The wide spacing of the older houses in the district is typical of building patterns in rural Middletown at the time.