An elite lakefront corridor north of Chicago had most of the top luxury residential sales in Chicagoland this year, with some North Shore homes reaching values never before seen in Illinois.
Six of the seven most expensive single-family home sales this year took place on a three-mile stretch of Sheridan Road between Winnetka and Kenilworth. Two of those homes, both in Winnetka, sold for more than $30 million, marking the most expensive homes sold in Chicagoland history.
And one agent, Jena Radnay of @properties Christie’s International Real Estate, was on one or both sides of all six of those North Shore deals. The preeminent dealmaker for the North Shore’s coveted lakefront properties, Radnay was the sixth-highest selling agent in Cook County in The Real Deal’s 2025 rankings, with $213 million in sales across 41 transactions.
The concentration of top-tier sales in the North Shore is a change from recent years, when neighborhoods like Lincoln Park, the Gold Coast and Streeterville dominated the list. The deals are also getting bigger. In 2024, three deals cleared $10 million, and in 2023 it was four. This year, the top six deals in Cook County all closed for more than $10 million.
Chicago’s luxury market took off in 2025, as strong stock market returns drove wealthy buyers toward real estate, and scarce inventory sharpened competition for trophy properties. In Cook County, 105 sales were over $4 million between October 2024 and October 2025, according to research by The Real Deal.
The run of luxury success is likely to continue into 2026. Billionaire Citadel founder Ken Griffin’s last Chicago property — the top-floor penthouse at the Park Tower — is under contract with a $12.5 million list price. And a spec mansion on the lake in Kenilworth is looking to beat the record in that village, asking nearly $17 million.
Here are the most expensive home sales in Cook County of 2025, based on TRD’s research.
609 Sheridan Road, Winnetka | $32.5 million
Just months after a neighboring mansion set the all-time record for a Chicagoland home sale, this 16,000-square-foot mansion snatched the crown with a $32.5 million off-market deal in November. Jeff Quicksilver, a co-founder of Walton Street Capital, and his wife Ashley Quicksilver, who owns a local fashion boutique, sold the French provincial-inspired estate.
They built the home in 2017 after tearing down the previous home on the 1.6-acre site. The design was led by architecture firm Northworks, with interior design by Kara Mann. The Quicksilvers bought that previous home for $8 million in 2013.
Radnay represented both the Quicksilvers and the buyer, who has not yet been identified. The deal also included about $2 million in personal property included in the house.
419 Sheridan Road, Winnetka | $31.3 million
This 13,894-square-foot lakefront estate held the title of Chicago’s priciest home resale for a few months, after selling for $31.3 million in August. Retired Goldman Sachs partner Muneer Satter and his wife, Kristen Hertel, sold the property. The estate features 223 feet of private beach, a boathouse and an infinity pool.
The seven-bedroom mansion, built in 1928 and designed by architect Ernset Mayo, underwent significant renovations under Satter and Hertel’s ownership. The couple first purchased the property in 2002 and bought an adjacent parcel in 2013. They spent tens of millions on renovations and additions on the estate.
Radnay represented both sides of the deal. The buyer was not identified in public records.
219 Sheridan Road, Kenilworth | $14.5 million
This 1907 Colonial Revival mansion traded for $14.5 million in October, becoming the most expensive home ever sold in Kenilworth. Built by Paul Starrett — the man who designed the Empire State Building — the 8,280-square-foot home was sold by designer Yoanna Kulas.
Kulas, who bought the home built in 1906 in 2020 for $4.5 million, renovated and modernized the interior while preserving its historic features. The renovations were led by architect Michael Abraham and luxury designer Mick De Giulio.
Radnay represented both Kulas and the unidentified buyers in the deal, which closed at nearly 97 percent of its asking price.
973 Sheridan Road, Winnetka | $12 million
This seven-bedroom coastal-style mansion kicked off the summer’s high-end frenzy when it sold for $12 million in June. The 9,650-square-foot home is decked out with amenities including a basketball court and golf simulator. It sits on a bluff with 100 feet of private beach.
The sellers were a trust associated with Luke and Margaret Kelly. They built the home in 2020 on the 1.75-acre site that they purchased for $6.19 million in 2017. John Baylor and Cricket King of @properties represented the seller, while Radnay brought the buyer. The home was bought under a land trust that obscured the new owner’s identity.
765 Sheridan Rd, Winnetka | $11.4 million
This 15,800-square-foot lakefront home sold for $11.4 million in July. The seller, Morris Silverman, bought the land for nearly $6 million in 2003 and finished the massive home in 2005. Silverman initially asked $18 million for the home in 2024, but cut the asking price to just under $12 million in February.
The interiors feature heavy detailing, including a Chagall-inspired mosaic ceiling and beveled mahogany floors. Outside, the property has a pool, an outdoor kitchen and 100 feet of private beach.
Radnay represented the seller, while Annie Flanagan of @properties represented the buyer, who isn’t identified in public records.
4 E Elm Street, PH23, Chicago | $10.1 million
The only Chicago property to sell for more than $10 million in 2025, this full-floor penthouse in the Gold Coast sold for $10.1 million in March. Former Fortune Brands CEO Bruce Carbonari and his wife, Kate Carbonari, sold the 5,400-square-foot unit, which they bought as raw space in 2016.
The unit features panoramic views and a 12-foot-high glass wall that opens to a balcony. Sharon O’Hara and Carrie McCormick of @properties represented the sellers, while @properties’ Emily Sachs Wong represented the buyers.
Other condos downtown have failed to crack $10 million this year, as the neighborhood has struggled to regain property values that dipped over the last few years. The closest was a penthouse at the St. Regis Chicago at 363 East Wacker Drive that sold for $9.25 million in October to Siri cofounder Dag Kittlaus.
381 Sheridan Road, Winnetka | $9.6 million
Three doors down from the second-priciest home of the year, the mansion at 381 Sheridan Road brought in $9.6 million when it sold in June. The home’s seller was Tom Day, CEO of Reyes Beer Division, who bought it for $7 million in 2022 from Neil Fitzpatrick, co-founder of quantitative trading firm Headlands Technologies.
The 8,100-square-foot Neo-Georgian home includes a theater, gym and sports simulator. Radnay represented the sellers, while Grace Flatt of @properties represented the buyers, who are not identified in public records.
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