Highwood is a diverse community with a lively downtown district
Named for its status as the tallest point between Chicago and Milwaukee, Highwood is a North Shore suburb known for its established downtown district. “It’s a community, with bars, restaurants and entertainment,” says Mike Del Monte, a broker with Coldwell Banker Commercial, who has more than 40 years of selling experience in Chicago’s North Shores. The suburb’s history has long centered around diversity, from the Irish and German immigrants working on the railroad during the 1800s, to the Northern Italian stonemasons and landscapers who sought work on nearby estates by the early 20th century. Generations of immigration formed a vibrant dining scene and a mix of cultures. "It's a small community with multifaceted residents," Del Monte says.
Waukegan Avenue and Green Bay Road are hubs for local dining
Dozens of eateries line Waukegan Avenue and Green Bay Road, where patrons fill outdoor dining spaces along the sidewalk or bars to enjoy live music. “There are a lot of locally owned old-school Italian places, like Maria’s Italian Bakery & Caffe,” Del Monte says. The homey spot sells classics like chicken vesuvio and cannoli. He also notes that the culinary scene has diversified beyond just Italian fare. “There’s Peruvian, Mexican and a very good French restaurant, Froggy’s French Café.” The latter has served the area since 1980. The community has several international grocers like Poeta’s Italian Food Mart and La Union Super Market. Sunset Foods offers a broader selection a couple of miles south. Target on Skokie Valley Road covers retail needs close to home, and Hawthorn Mall, 9 miles away, features over 120 stores.
A mix of vintage cottages, midcentury styles and newer construction
The community has narrow streets flanked by mature maple and oak trees, providing shade for sidewalks and homes. These houses range from late 19th-century workers' cottages to recently built New Traditional styles. “Most of the housing stock was built during the mid-20th century,” Del Monte says. “It’s got that old-timey district feel to it, and it's more affordable than surrounding neighborhoods like Lake Forest Highland Park.” Highwood’s median sales price for single-family homes is $410,000, significantly lower than Highland Park's median of $780,000. Homes needing repair start at around $200,000, while larger, custom residences can sell for just under $2 million. Townhouses are also available and range in price from $625,000 to $890,000. Highwood supports a relatively even mix of renters and owners.
Highland Park High School offers dual credit courses
Wayne Thomas Elementary receives an A from Niche, and Northwood Junior High has an A-minus. Highland Park High, rated A-plus, offers dual credit courses at Lake County High School Technology Campus in Grayslake. Students can take classes ranging from automotive services and culinary arts to cybersecurity.
Recreation includes local parks, a nearby preserve and more
Residents have access to several recreation areas in and around the community. Everts Park has open green space for picnics and a recently renovated playground. Del Monte says Sheridan Forest Preserve is a popular place to spend time outdoors. There are a series of walking trails that wind through the park and down to Lake Michigan’s sandy shoreline. Highwood Recreation Center hosts year-round programming, including youth sports and fitness classes like Zumba and yoga. Other nearby attractions include the Chicago Botanic Garden and Sunset Valley Golf Club, which has an 18-hole course open to the public.
Community traditions thrive at Highwood Days and Everts Park
Though seasonal events bring neighbors together throughout the year, Highwood Days stands out as a community staple. The long-running annual tradition occurs downtown over four days in mid-July, featuring food vendors, carnival rides and more. Every Wednesday evening from early June through late August, Everts Park fills for Highwood Evening Gourmet Market, which serves up live music, drinks and features over 60 vendors selling fresh goods and handmade gifts.
Getting around on U.S. Route 41 and Interstate 94
U.S. Route 41 is the area’s main north-south highway. Residents can use the route to access I-94, which leads to Chicago, 30 miles south. Metra’s Union Pacific North Line passes through Highwood Station, offering 50-minute rides into downtown. Pace buses service stops along main roads. The nearest commercial flights take off from Chicago O’Hare International Airport, 20 miles south. Endeavor Health Highland Park Hospital is closer to home on Park Avenue.
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Written By
Matthew Simmons
