Culture, Coastline, and the North Shore's Most Vibrant Downtown
The land now called Highland Park has been inhabited for a very long time. A traveler in 1833 described eating roasted corn with a Potawatomi chief at a site likely near present-day Clavey Road. European settlement arrived in 1834 with William Biggs, who established a farm on the bluffs. In 1847, two German immigrants founded a small settlement called St. John’s along the lake, though disputes over land ownership caused it to be abandoned. A second attempt by Jacob Clinton Bloom in 1850 produced Port Clinton, just south of the original site. When the railroad arrived in 1854, the community was renamed Highland Park, and with it came the thing that changed everything: direct daily access to Chicago.
A group of Chicago businessmen incorporated the city in 1869 with a vision for a scenic lakefront retreat from urban life. The railroad made that vision practical, and Highland Park grew steadily through the late 19th and early 20th centuries into one of the most established residential communities on the North Shore. Its location, 25 miles north of the Loop, made it accessible without being adjacent, and that balance of proximity and remove has defined its character ever since.
The oldest standing structure in the city, a log cabin built in 1847 from hand-hewn white oak timbers, is preserved today at Exmoor Country Club, which gifted it to the Highland Park Historical Society. The Central Business District developed along what is now Second Street and Central Avenue, and the Ravinia district, at the southern end of the city, emerged in the late 19th and early 20th centuries as an artists’ colony, geographically and culturally distinct from the commercial downtown. Both continue to function as active commercial and community districts today.
Ravinia Park opened on August 15, 1904, originally as an amusement park built by a railroad company to generate weekend ridership. It became a music venue, then an institution. The Chicago Symphony Orchestra has made Ravinia its summer home since 1936. Ravinia is now the longest-running outdoor music festival in North America, welcoming approximately 400,000 guests to over 100 events each season. It is the only private Metra stop in Illinois, and the train runs directly to the festival entrance during summer performances. For Highland Park residents, Ravinia is not a destination they drive to from out of town. It is simply part of summer life.
On July 4, 2022, a mass shooting at the city’s Independence Day parade killed seven people and injured dozens more. The event was a profound trauma for the city and the broader North Shore community. Highland Park has continued to function as a close-knit, active, and civic-minded community, and has resumed its Independence Day traditions in subsequent years with community support and an active commitment to public safety.
Living in Highland Park
Highland Park’s housing stock is one of the most varied on the North Shore, shaped by 170 years of development across twelve square miles of varied terrain.
The eastern sections of the city, near the lake bluffs and ravines, hold the oldest and most architecturally significant homes. Historic Colonials dating to the mid-1800s sit alongside Arts and Crafts houses, Tudor Revivals, and the early 20th-century estates that defined North Shore residential architecture in that era. The ravines, some extending nearly a mile inland from the lake, created natural boundaries that preserved green corridors through these older neighborhoods. Frank Lloyd Wright designed homes in Highland Park, and the city’s commitment to architectural preservation has kept much of this stock intact.
The central and western sections of the city hold a broader range of housing types, including mid-century ranch homes and Colonials, contemporary custom builds, and a meaningful supply of downtown condominiums and townhomes near the Central Business District. This wider range makes Highland Park more accessible at entry-level price points than Lake Forest or Lake Bluff while still offering lake-adjacent properties at the full luxury end of the market.
The median home price in Highland Park has been running between approximately $735,000 and $782,000 depending on the data source and measurement period, with the Zillow average home value around $735,000 reflecting a 6.5% year-over-year increase. Movoto data from September 2025 showed a median sold price of $995,000, reflecting the weight of higher-end transactions in that period. The market has been competitive, with homes averaging 35 to 42 days on market and receiving multiple offers on well-priced properties. The city’s supply of downtown condominiums provides entry points well below the single-family median, and lakefront and bluff-adjacent properties trade at significantly higher levels.
Highland Park has four Metra Union Pacific North Line stations within city limits: Braeside, Ravinia Park, Ravinia, and Highland Park. This density of train access is unusual even by North Shore standards, and it gives residents meaningful flexibility in how they access the city depending on their home location. The Ravinia station, of course, becomes the city’s most famous transit stop each summer, when Metra runs special service for festival evenings. Route 41 runs north-south through the city, and Interstate 94 provides highway access westward toward O’Hare, approximately 18 to 20 miles away. The Skokie Valley Trail runs through the city for bicycle commuting and recreation.
Businesses and Local Life
Highland Park operates two distinct commercial districts, each with its own character, and neither feels like a generic suburban strip.
The Central Business District along Second Street and Central Avenue is the city’s main commercial core. It is genuinely pedestrian-scaled and genuinely local, with independent restaurants, boutique retail, galleries, and professional services filling a walkable several-block area. Friday night concerts at Port Clinton Square run through the summer. The Taste of Highland Park, Stews and Brews, a Vintage Car Show, and Oktoberfest anchor the seasonal festival calendar. The Port Clinton Art Festival, held annually downtown, is one of the most respected juried outdoor art shows in the region. Wayfarer Theaters, a newer addition to the downtown cultural scene, provides a boutique cinema and live events space that has filled a longtime gap in the city’s programming.
The Art Center Highland Park presents museum-quality exhibitions and runs arts education programming for all ages, serving as the city’s primary visual arts institution alongside the many independent galleries clustered in and around the downtown. Heller Nature Center, a 97-acre preserve of oak-hickory forest, tall grass prairie, and oak savanna on the city’s west side, offers trails, environmental education, and one of the more unexpected natural escapes in any North Shore suburb.
The Ravinia District, east of Green Bay Road along Roger Williams Avenue, is an entirely different kind of commercial neighborhood. Its roots as an artists’ colony in the late 19th and early 20th centuries are still legible in its scale and feel, with small-scale restaurants, specialty shops, and services in a walkable cluster of historic buildings. Food Truck Thursdays fills Jens Jensen Park every Thursday evening through the summer. The Ravinia Farmers Market runs year-round, with summer Wednesday markets at Jens Jensen Park from June through October and winter indoor markets at Wayfarer Theaters and Braeside Market on Saturdays and Fridays respectively. The Ravinia Speakeasy, Chunky Scones, and a range of independent dining options make the district a destination before and after festival performances.
Ravinia Festival itself, of course, is Highland Park’s defining cultural institution. More than 100 concerts each season, 40-plus artist debuts, the Chicago Symphony Orchestra as summer anchor, and programming that ranges from classical to jazz to rock to world music on multiple stages. The lawn at Ravinia, where residents spread blankets and picnic under the trees while the music carries across the park, is one of the great North Shore summer experiences and one that draws people from well beyond Lake County.
For outdoor recreation, Highland Park’s Park District manages over 700 acres of parkland. Rosewood Beach, accessible at the base of the bluffs, is the city’s primary swimming beach, with a boardwalk running its length and a park above the bluff. Moraine Beach is open to dogs and their people. Park Avenue Beach includes boating facilities and a recently renovated breakwater and boat ramp. Sunset Valley Golf Course, one of the earliest-built courses on the North Shore, underwent a $7 million renovation in 2018 and remains one of the most well-regarded public courses in Lake County. The Chicago Botanic Garden, a world-class horticultural institution, sits just south of Highland Park in neighboring Glencoe, within easy driving and biking distance for residents.
Highland Park is the North Shore community that has the most going on. Two walkable commercial districts. Four Metra stations. Six miles of lake shoreline with accessible beaches. A music festival that is genuinely world-class by any standard. A natural landscape of bluffs and ravines that preserves a sense of wildness within the city limits. And a civic culture that invests seriously in arts, parks, schools, and public life. For buyers who want the full North Shore experience at a price point more accessible than the communities further north, Highland Park delivers.
Ready to explore homes for sale in Highland Park? Browse current listings below, or reach out to discuss what’s available and what fits your goals.
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