Highwood enjoys the good life with a thriving dining scene, festivals, and nightlife that attracts visitors from across the North Shore.

The city is known for its award-winning restaurants, offering everything from Italian to French cuisine. In the summertime, residents enjoy Highwood’s popular Evening Markets, recognized among the best on the North Shore for its numerous vendors and variety of musical acts.

Additional community events include Highwood Days, the city’s oldest festival. The city is also home to one of the area’s premier bocce facilities, Highwood Bocce Club.

Aptly named for its high elevation relative to Lake Michigan and its wooded setting, Highwood is located just north of Highland Park. Real estate 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 a U.S. military base.  

The main highway to Highwood is U.S. 41, which connects Chicago to Milwaukee. Commuter rail service includes two Metra train stations offering direct access to downtown Chicago.

Highwood map

Featured Highwood Listings

Here are 12 out of 8 listings in Highwood


Milwaukee District North line at Lake Forest Metra

Union Pacific North line at Fort Sheridan Metra
Average Sale Price
Average Days On The Market
Sales Prices VS. List Price
Data represents the community area's average over the past 12 months. All information deemed reliable, but not guaranteed.

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