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Lakefront Winnetka mansion listed at $3M over last trade

Luxury market is humming, but sellers often take losses

Lakefront Suburban Chicago Mansion Listed for $10.3 Million

The head of a national beer distributor recently listed his 5,500-square-foot mansion in Winnetka for $10.3 million.

Tom Day, CEO of Reyes Beer Division, and his wife Amanda are asking $1,872 per square foot for their lakefront mansion at 381 Sheridan Road, Crain’s reported. Jena Radnay of @properties Christie’s International Real Estate is representing the sellers through a private agents-only network.

A sale at $10.3 million would represent a 47 percent increase over the home’s previous trade. Day and his wife paid $7 million for it in 2022. That transaction penciled out to $1,272 per square foot. 

They bought it from Neil Fitzpatrick, co-founder of quantitative trading firm Headlands Technologies. Fitzpatrick purchased the Winnetka property for $12 million in 2018.

The two-story home features six full bathrooms, two half bathrooms, a great room with cathedral ceilings, and a black marble fireplace. It also includes high-gloss Farrow & Ball lacquered walls and Schumacher wallpapers.

It has a sports simulator room, theater, office, lounge, gym and guest suite. Outside, the neo-Georgian-style home features a gated entrance, a three-tiered terraced patio with lake views, a bathing veranda and a sandy beach.

Day’s mansion joins Radnay’s lineup of other elite properties, including Morris Silverman’s 15,700-square-foot mansion at 765 Sheridan Road, which has been relisted for just under $12 million, a significant reduction from its previous $18 million price. Radnay is also representing retired investment banker Muneer Satter’s $35 million mansion at 419 Sheridan Road. 

The Chicago luxury market is surging, with over 100 transactions priced at $4 million or more last year, indicating a potential comeback for the sector. However, the market is also facing challenges, as many sellers are trading at significant losses, reflecting ongoing inventory issues and high construction costs.

— Andrew Terrell

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