Sleepy Hollow is a strictly residential community in Kane County with a population of 3,300. Named after the popular story by Washington Irving’s The Legend of Sleepy Hollow, many of the city’s streets and lakes are also named after characters in the story.Originally a farm area, the town’s founder Floyd T. Falese hired an architect to design the infrastructure and residential development that we know today. The pattern successfully avoided destruction of a single tree in the entire community, and retained its rural charm.
Sleepy Hollow consists of five neighborhoods: Deer Creek, Saddle Club Estates, Sleepy Hollow Manor, Surrey Ridge, and the newest addition The Bluffs. The town falls under school District 300, with most residents attending Dundee Crown High School.
Like its founder, the town has a strong sense of pride for the planning and work that went into its design. Celebrations like Fourth of July, dances, Halloween parades, community bonfires, and the notorious ride of the Headless Horsemen bring this community together to celebrate country living and uniqueness that separates them from their Dundee and Carpentersville neighbors.