Winnetka Mansion Sells at Record Price That’s Also a Discount

Chicago’s second-priciest home sale of this year just closed on the North Shore.

Tom Day, CEO of Reyes Beer Division, sold his lakefront Winnetka mansion Friday for $9.6 million, Crain’s reported. It’s second to a $10.1 million Gold Coast penthouse that sold in March.

The six-bedroom home at 381 Sheridan Road spans 8,100 square feet on nearly an acre overlooking Lake Michigan. The price comes out to about $1,184 per square foot.

Jena Radnay of @properties Christie’s International Real Estate represented the sellers. The buyers, not yet named in public records, were represented by Grace Flatt, also with @properties.

Built in a neo-Georgian style, the home features a gated drive, a three-tiered patio, sports simulator, gym, theater, guest suite and private beach access. Interiors include high-gloss lacquered walls, cathedral ceilings in the great room and a black marble fireplace.

The Days bought the home in 2022 for $7 million from Neil Fitzpatrick, co-founder of quantitative trading firm Headlands Technologies. Fitzpatrick paid $12 million for the property in 2018.

The recent sale closed at roughly 93 percent of the Days’ $10.3 million asking price. They first marketed the property privately in early March before it went public on the MLS in April and quickly went under contract.

The Days upgraded the home further after purchasing it. Listing photos showed a sleek, white kitchen and lake-facing terraces that lead down a bluff to the private shoreline.

The sale is Winnetka’s top recorded price since August 2023, though it may not hold that title for long. Two other homes listed at over $12 million have been under contract since March, and a $35 million private listing is reportedly pending.

The deal comes amid a resurgent luxury market in the North Shore suburb, with more than 100 homes selling above $4 million across the Chicago area last year. Still, many top-tier homes are trading at a loss compared to late-2010s peak values, with high construction costs and persistent inventory challenges.

— Judah Duke