Located just north of Highland Park, approximately 24 miles north of downtown Chicago, the city of Highwood is known for its thriving dining scene which attracts diners from all over the North Shore and beyond. The community reportedly was named after its wooded setting and high elevation relative to Lake Michigan.

Real estate in Highwood varies from duplexes and ranches to luxury apartments, condominiums, and single-family homes. The community also includes part of Fort Sheridan, a master-planned residential community and national historic landmark that was originally developed as a U.S. military base.  

Award-winning restaurants abound in Highwood, offering everything from Italian to French cuisine. During the summer, residents enjoy exploring vendors and listening to a variety of musical acts at Highwood’s Evening Markets, which has been recognized as one of the best markets on the North Shore. Other popular community events include the annual Holiday Lighting Ceremony and Highwood Days, the city’s oldest festival. Highwood is also home to the Highwood Bocce Club, one of the area’s premier bocce facilities.

Nearby Public Transportation

Union Pacific North

at Highwood Metra, Fort Sheridan Metra

School Districts

Twp Hsd 113

North Shore Sd 112

Elementary Schools

Middle Schools

Data supplied by the National Center for Education Statistics

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Average Sales Price


Average Days on Market


Sales Prices vs. List Price


Data represents the average over the past 12 months. All information deemed reliable, but not guaranteed.