[5] Sleepy Hollow is generally bounded by Randall Road to the west and Illinois Route 72 to the north.

The village is on the site of Sleepy Hollow Farm, which was owned by the late J. H. McNabb, board chairman of Bell and Howell Company.

Falese retained the services of a prominent planner and landscape architect, Raymond W. Hazekamp, who laid out a pattern of meandering roads, without curbs or sidewalks, that wound into curvilinear cul-de-sacs, avoiding the destruction of a single tree.

This design retained the rural charm and natural contours of the farm and avoided taking down any existing trees.

[10] Falese developed lakes in Sleepy Hollow from existing springs and stocked them with fish.

The designs were carefully selected to enhance what Falese called "the Sleepy Hollow concept of good living".

Falese marketed lots in the unincorporated subdivision called "Sleepy Hollow Manor".

In 1958, the residents voted to incorporate Sleepy Hollow as a separate village rather than being annexed to West Dundee.

The only commercial activity was the Sleepy Hollow Resort Motel (later renamed the Chateau Louise) and Crichton's Super Mart.

[13] In 1966, the Glen Oak Country Club was opened as a member-supported outdoor pool facility (which was later transferred to the Dundee Township Park District.

[17] On March 9, 2014, the Sleepy Hollow police force had its first fatal shooting in a domestic disturbance case.