W ith a budget of $5 million, you could buy a three-bedroom apartment in Manhattan or a four-bedroom waterfront condo in Miami. On the North Shore, that same figure delivers a lifestyle all its own – think sunrise yoga on a private beach in Highland Park, tennis matches at a storied Lake Forest estate that graced the big screen, or garden parties at a Winnetka residence reminiscent of France. LUXURY SALES SURGE $5 million is often considered a benchmark for the Chicagoland luxury market, which is seeing record activity on the North Shore. Through the end of August, 15 homes priced at $5 million and above changed hands in the area, compared with seven sales during the same period last year. Seven properties are currently under contract with list prices ranging from $5.295 million to $15 million. “At this level, it’s all about lifestyle,” says @properties Christie’s International Real Estate broker Jena Radnay, who was involved in several of those transactions in 2025, including a record-breaking $31.25 million sale in Winnetka. While some wealthy locals have moved out of state for a change of scenery, many have upgraded their homes here. Radnay adds that demand is strong as “people understand the value of the North Shore more than anything.”
$5 MILLION, FIVE WAYS Recent transactions and listings show just how many different forms $5 million can take on the North Shore. On Woodley Road in Winnetka, Radnay represented a meticulously renovated 11,000-square-foot home built in 1936. Set on 1.4 acres, the French-inspired residence features light-filled interiors that open to lush gardens. The property sold for $4.975 million in April. A few doors down, @properties Christie’s International Real Estate brokers Katie Hackett and Ann George are listing another Woodley Road estate with an asking price of $4.95 million. The nearly 10,000-square- foot home was built in 1943 and sits on 1.9 acres of park-like land.
ASPIRE ON THE SHORE // 55
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