Another Lakefront Mansion Sells in Chicago Suburb Winnetka

A lakefront mansion in Winnetka sold for just under $9.5 million, one of several high-dollar deals to hit the North Shore enclave this summer.

The 12,700-square-foot estate at 139 Sheridan Road sold this week at its most recent asking price after a series of price cuts, the Chicago Tribune reported. Originally listed in May 2024 for $11.75 million, the home underwent multiple reductions before finding a buyer in April for $9.475 million, about $746 per square foot.

Built in 2021 by the Morgante Wilson architectural firm, the six-bedroom property sits on a three-quarter-acre lot with direct Lake Michigan access and a walkout lower level that opens to a private beach. Listing agent Jena Radnay of @properties Christie’s International Real Estate described the home as a “like-new beach house retreat” that couldn’t be rebuilt under current Winnetka shoreline ordinances.

The seller, a retired executive vice president of labor relations for United Airlines, paid $4 million for the land in 2018. Public records do not yet identify the buyer, who purchased through an opaque land trust.

The deal adds to a string of luxury sales on Sheridan Road, a stretch that’s a magnet for ultrawealthy buyers looking for lakefront seclusion within reach of Chicago.

Last month, Tom Day, CEO of Reyes Beer Division, sold a 5,600-square-foot home at 381 Sheridan Road for $9.575 million, while a 15,800-square-foot property at 765 Sheridan Road traded hands for $11.4 million on July 9. In June, a 9,700-square-foot mansion at 973 Sheridan Road sold for $12 million in the area’s priciest sale of the year so far.

Those sales suggest sustained appetite at the top of the suburban market despite broader market jitters. Luxury listings in Winnetka tend to linger, but when they move, they often do so in clusters — especially along Sheridan Road, where lakefront supply is tightly constrained.

— Judah Duke