Condos & Lofts in Highwood


About Highwood

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

Highwood features award-winning restaurants with diverse cuisines including Italian and French. In the summertime, residents enjoy Highwood’s popular Evening Markets, recognized as among the best on the North Shore. Visitors can explore numerous vendors and enjoy a variety of musical acts.

In addition, community events abound including the annual Holiday Lighting Ceremony and Highwood Days, the city’s oldest festival. The city also is 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, the city of 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.  

Developed before the suburban housing boom, you’ll find pre-war residential and commercial buildings – from neo-classical and Italianate to arts and crafts and bungalow styles. The business district features brick buildings with storefronts and businesses on the ground floor and residential apartments above.

The main highway to Highwood is US-41, which connects Chicago to Milwaukee. Commuter rail service includes two different Metra stations within the city; and easy access to nearby stations with trains running from Kenosha to downtown Chicago.