Sleepy Hollow, IL Homes for Sale & Real Estate

Sleepy Hollow, Illinois, is a charming village in Kane County, just 38 miles northwest of Chicago, with a population of 3,214 as of the 2020 census. Nestled between West Dundee and Elgin, this serene suburb is known for its rolling, wooded landscapes and lack of a traditional grid-like street pattern, a design choice by developer Floyd T. Falese in the 1950s to preserve the area’s rural charm. Originally part of Sleepy Hollow Farm, the village was thoughtfully planned with meandering roads and custom-built homes, retaining natural contours and trees while incorporating lakes like Paula, Sharon, and Ichabod. Sleepy Hollow offers a tight-knit community atmosphere, featuring parks, trails, and annual events like the Fourth of July Festival and Halloween in the Hollow, which celebrate its unique history and connection to Washington Irving’s “The Legend of Sleepy Hollow.” Despite its quiet, suburban feel, the village is conveniently located near major routes like Illinois Route 72 and Randall Road, providing easy access to urban amenities.