Sleepy Hollow, IL

Sleepy Hollow is a quiet village located between Elgin and West Dundee, about 40 miles northwest of Chicago. Developed from farmland in the 1950s, the community is known for its winding, tree-lined streets and small lakes named after Washington Irving’s classic tale. With just over 3,000 residents, the neighborhood offers a relaxed, semi-wooded feel, while Randall Road and Route 72 keep everyday shopping and commutes quick and simple.

Families are often drawn here for the spacious lots, local parks, community pool, and Sleepy Hollow Elementary School right in town. Students continue through the broader Community Unit School District 300 for middle and high school. It is an easy place to settle down if you want peaceful residential living that still sits minutes away from downtown West Dundee’s restaurants and riverfront spots.