It primarily consists of fifteen single-family homes representative of the Prairie School and Craftsman styles of architecture.

[3] The first fourteen homes on Oak Circle were platted in 1907 as part of Joseph Woodruff's Addition to Wilmette.

Oak Circle was paved in 1911, and homes on the west side of the street were likely built between 1917 and 1920; however, the permits indicating the precise dates of their construction were lost in the 1920 Palm Sunday tornado outbreak.

[3] Twelve of the fifteen homes in the Oak Circle Historic District are bungalows, and they exhibit various elements of the Craftsman and Prairie School movements.

Craftsman elements in the houses generally included low, gabled roofs, overhanging eaves, decorative beams, and materials such as wood, stone and brick.