Chicago’s North Shore: Land of trophy homes and sky-high price tags

Chicago’s North Shore real estate market is defying expectations and the laws of gravity. In Winnetka, Kenilworth, and Lake Forest, sales of high-end homes are not only rising, but also setting records. As of the end of last month, 76 homes in the Chicago area have sold for $4 million or more, a half-year record that has already eclipsed most full-year totals before 2021.

Much of this activity is concentrated along the Lake Michigan shoreline, where luxury properties once considered niche are now must-haves. Many of today’s high-end buyers are flush with gains from the surging stock market or reallocating wealth into tangible assets as a hedge against economic uncertainty. In an interview with Crain’s Chicago Business, Carrie McCormick, an agent with @properties Christie’s International Real Estate, said about the trend, “They’re putting their investments into hard assets,” McCormick said. “In real estate, they want trophy assets. These are properties so rare and desirable that they become part of a personal portfolio. It’s not just about square footage. It’s about legacy, prestige, and a view nobody else can buy.”

The uptick in all-cash purchases isn’t just a show of wealth; it’s a strategic move. With high mortgage rates and limited luxury inventory, cash offers often seal the deal faster and with fewer complications. Buyers are showing up with serious cash, confident in the long-term value of North Shore real estate.

Factors such as climate risk, tax pressures, and insurance costs in coastal states like Florida and California are prompting investors to move to the Midwest. “They know we’re lucky to have what we have on the Lake Michigan shoreline,”agent Jena Radnay of @properties Christie's International Real Estate told Crain’s. “No sharks, no fires, and property that’s undervalued compared to the places they’ve traveled.”

That "undervalued" perception is shifting rapidly. A lakefront Winnetka home with 100 feet of private beach sold for $12 million this June, while a Kenilworth property is asking $15 million, more than $3 million above the town’s recent record sale. Demand is also spilling into Lake Forest, where a Beaux-Arts mansion sold for $6.2 million, only the third home in the area to crack the $6 million threshold in two decades.

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Why the rush? The answer, in part, is scarcity. The inventory of available homes remains tight across the region. According to Redfin, new listings in Lake County reached a record median asking price this spring, and yet, sellers still hold the advantage. “I wrote 20 offers over the weekend,” said Americorp Real Estate’s Matt Laricy. “We only won one.”

While some sellers test the upper limits, many listings are selling quickly and are being sold over asking price. “Sellers are absolutely reaching higher,” Laricy said. “People aren’t waiting anymore. They know mortgage rates aren’t dropping to the threes again. They’re buying now.”

As valuations rise, so do assessments. Cook County recently pegged 15 lakefront New Trier homes at $16 million or more. That’s up from just two properties assessed at that level in 2022. “A lot of people sitting in these lakefront houses were shocked when they opened their assessment letter,” said Radnay. And with new bluff restrictions in Winnetka limiting buildable land, some homeowners argue that their real-world property values may actually shrink.

Even so, the top end of the market continues to surge. The first half of 2025 has already outpaced the record year of 2022 for sales above $4 million, and many believe that pace will continue. “It offers validation that Winnetka is the right place to invest,” Radnay said, referring to billionaire Justin Ishbia’s $78 million lakefront estate under construction.

In short, North Shore luxury isn’t just in demand, it’s become a strategic purchase. The view may be priceless, but in 2025, the price tag is climbing fast.