Winnetka's Home Alone legacy fuels a rising North Shore luxury market

Winnetka, Ill., a quiet suburb north of Chicago, remains a magnet for luxury buyers and pop-culture fans alike, in part because of its fame from the 1990 film Home Alone. The iconic mansion used as Kevin McCallister's home sits on 671 Lincoln Avenue and has become a symbol of the village's upscale appeal. The roughly 10,000-square-foot residence features five bedrooms and extensive amenities that attract visitors during the holidays. The suburb ranks among the safest and wealthiest communities in the country, according to GOBankingRates, with a median home price around $2.2 million in Cook County data. Earlier this year, the Home Alone house sold for $5.5 million and, within months, was estimated at about $5.7 million in current market chatter.

Not far from the Lincoln Avenue property, another Winnetka estate drew headlines in September by selling for $31.25 million, setting a record for both the neighborhood and the state. The Windsor House spans nearly 14,000 square feet and includes seven bedrooms, nine bathrooms and four half-baths, plus private beachfront access with a state-of-the-art boathouse, a boardwalk, a pool and a spa. Real estate brokers described the listing as unrivaled in Winnetka's premier locale, underscoring the area's pull for buyers seeking expansive lakefront property.

Alongside the marquee properties, Winnetka's everyday pull is rooted in location, schools and lake access. The Home Alone house at 671 Lincoln Avenue remains a standout, while the Windsor House addition to the lakefront scene signals a broader trend of high-end development on the North Shore. A separate high-profile project is in the works: Justin Ishbia, a Phoenix Suns co-owner, is developing a projected 77 million-dollar estate that would be among the most expensive in Illinois once completed. In real estate terms, Winnetka's downtown holds a mix of boutique shops, upscale eateries and well-regarded schools, with the Plaza Del Lago shopping center in nearby Wilmette offering additional luxury retail.

Real estate pros say the market's recent heat is part of a longer trend for the Chicago area's North Shore, where low inventory meets steady demand. Dawn McKenna of the Dawn McKenna Group, who sold the Home Alone mansion, notes that Winnetka's fundamentals—such as lake proximity, large lots, updated homes and a strong school system—drive value beyond the novelty of film lore. McKenna also pointed to how the surrounding area has evolved, with new developments and a broader assortment of amenities that keep the village desirable year-round.

Outside the core Winnetka village center, the broader North Shore features a mix of historic architecture, tree-lined streets and lake access. The downtown districts of East Elm, Hubbard Woods, West Elm and Indian Hill offer boutique shops and dining, from Little Honeycomb and 501 Local to Pomeroy, a French bistro, and Mino's, an Italian standout. The holiday season in Winnetka routinely draws visitors for Christmas on Evergreen, a light-display tour at 145 Evergreen Lane, as well as a village tree lighting and an annual Winter Wanderland event. The Home Alone association continues to draw attention during holidays, but residents say the town’s charm—along with its walkability, architecture and lakeside life—remains the true draw.

Looking ahead, Winnetka also is planning a downtown expansion that would add 59 luxury apartments, adding to a continuing trend of new, high-end development in the area. The broader market around Winnetka saw the area around Wilmette's Plaza Del Lago, and the region continues to attract buyers who value access to Chicago, a strong school system, and a sense of place that blends small-town charm with big-city amenities.