Winnetka Sets Pace on Chicago’s Buzzy Luxury Market

Chicago’s priciest housing tier is setting a torrid pace this year, with more homes trading at $4 million and up in the first eight and a half months than in all of last year — and nearly four months still to go.

From Jan. 1 to this week, 109 homes sold in the luxury range, eclipsing the 106 that traded hands in all of last year, Crain’s reported. That total was already the second-highest ever, behind 2022’s record 136. If momentum holds, 2025 is on track to challenge or top that peak.

Much of the action is in Winnetka, where @properties Christie’s International Real Estate agent Jena Radnay has dominated the leaderboard, repping one side or both in five of the year’s top six deals. The suburb notched the year’s headline-grabber: a 22-room lakefront estate that went for over $31 million, the highest price ever paid for an existing home in the Chicago area. Radnay told the outlet that Winnetka’s mix of investment value and lifestyle draw buyers fast when properties enter the market.

Chicago itself has notched a majority of the high-ticket sales this year. A Gold Coast condo crossed the $10 million mark, and Ken Griffin quietly sold two unfinished Gold Coast floors for a combined $15.9 million — deals that could end up ranking higher once ownership details are clarified. So far this year, 64 of the 109 luxury sales have been in Chicago.

The run isn’t just about wealth cushioning buyers from inflation. Radnay said families are betting on long-term appreciation and paying premiums for lakefront security. Carrie McCormick of @properties Christie’s said that scarcity drives urgency.

There’s still potential reshuffling ahead, with a pair of pending suburban sales near $15 million in Kenilworth and Lake Forest. Even so, nothing comes close to Winnetka’s record-setter.

Chicago’s luxury market has come a long way since the 2010s, when $4M deals averaged around 50 a year. Prices have swelled in the 2020s, with Redfin data showing the metro’s median home price up 73 percent since 2019. — Eric Weilbacher