Two $12 Million Mansions Sell in Chicago Suburb Winnetka

In Winnetka’s residential market, eight-figure deals are coming in waves.

Two $12 million sales landed within just eight days of each other, the latest in a hot streak for the ultra-luxury market in the lakefront Chicago suburb, Crain’s reported.

Both homes are on Sheridan Road and have 100-foot wide private Lake Michigan beachfronts. They are among the priciest deals in the area this year, along with a $35 million mansion that went under contract in early February.

The 9,650-square-foot, seven-bedroom home at 973 Sheridan Road, was built five years ago on about 2 acres. It was listed on Feb. 15 and went under contract in 12 days. The asking price came to $1,245 per square foot.

Built in 2020 by Paul Konstant and Scott Lyon & Company, the two-story mansion has an elevator, a sports court, golf simulator, home theater, playroom with bunk room and a guest house with designated parking.

The land was purchased for $6.19 million in 2017 by a trust associated with Luke and Margaret Kelly. Agents Cricket King and John Baylor with @properties Christie’s International Real Estate had the listing.

The mansion at 765 Sheridan Road was built in 2005. The 15,800-square-foot, seven-bedroom home includes a pool and spa, stone terraces, an outdoor kitchen, gym, bar and elevator. It asked about $760 per square foot.

It initially hit the market in August for $18 million. After a price drop to just under $15 million, sellers Morris Silverman and Lori Komisar switched agents to Jena Radnay of @properties Christie’s and reduced the price to just under $12 million.

This year’s highest-priced home sales so far include two downtown Chicago condos in the $8.9 million range at the St. Regis on the Chicago River and One Chicago at Chicago Avenue and State Street.

Two Winnetka homes sold for over $12 million in 2023, and one in 2022, when billionaire private equity executive Justin Ishiba assembled a $39.9 million site for a mansion projected to cost over $44 million to build.

Another Winnetka home, which hit the market Friday, is asking $10.3 million ($1,275 per square foot) at 381 Sheridan Road.

Built in 2015, that 8,000-square-foot home has six bedrooms, a theater room, sports simulator, home gym, two spa baths and two walk-in closets. It has an outdoor kitchen, an 88-foot wide private beach and a 3-car garage.

The sellers are Thomas and Amy Day, Cook County records show. Radnay has the listing.

— Judah Duke