Breaking Down Chicagoland’s Luxury Home Sales

Luxury real estate is entering new territory in Chicagoland, but record-setting prices aren’t necessarily boosting prospects of all sellers as several high-end deals resulted in losses.

November brought about another record-setting home sale for Chicago, along with the movement of some long-sitting downtown condos as the usually sleepy holiday season approached.

A 16,000-square-foot mansion at 609 Sheridan Road in Winnetka fetched $32.5 million in the most expensive home resale in Illinois history on Nov. 19. The buyers paid $2 million more for personal property in the home, for a total price of $34.5 million.

The home was sold by Walton Street Capital co-founder Jeff Quicksilver and his wife, Ashley, who owns the Athene fashion boutique in Winnetka. The Quicksilvers had the French Provincial style home built in 2017.

The sale marked another win for @properties Christie’s International Real Estate agent Jena Radnay, who represented both sides on the deal. Radnay set the previous record just a few months ago with the sale of another Winnetka lakefront house for $31.3 million.

Radnay has represented one or both parties on the top six most expensive Cook County home sales this year, leveraging her expertise of the North Shore lakefront to close deals. The demand for luxury lakefront homes in the ritzy northern suburbs has hit a fever pitch in the last year, pushing prices to numbers rarely seen in the Midwest.

Elsewhere, Lake Geneva saw its strong fall continue into November, with three waterfront houses trading there for more than $6 million.

Yet the luxury condo market in downtown Chicago is still struggling.

Here’s a breakdown of the biggest residential deals closed in November and what they show about the market.

Lake Geneva continues rally

Leading the list of luxury Lake Geneva sales in November was a 7,100-square-foot house at 831 Bayview Drive.

The home sold in a quiet, off-market transaction for $8.3 million on Nov. 17. The buyers didn’t come from far: Philip and Melody Lekousis, who bought the house, sold a 3,300-square-foot house on Park Drive for $6 million earlier that month, trading up for the bigger Bayview Drive house.

Compass agent Daniel Oleston represented the sellers, and Wendy Murphy with Mahler Sotheby’s International Realty represented the buyers.

The sale rounded out a busy fall as several lakefront homes hit the market in Lake Geneva, taking advantage of surging demand for luxury property near Chicago. The house was the seventh lakefront home to sell there since October, and the fourth to fetch a price of more than $8 million.

In addition to the Lekousis’ Park Drive house, a lakefront property at 8 Hillside Drive in Lake Geneva sold for $7.4 million last month.

William Farley cuts losses downtown

After two years on the market and a series of price chops, former Fruit of the Loom CEO William Farley and his wife Shelley finally unloaded their spacious Gold Coast penthouse for $7.5 million, less than half of their original $16 million asking price.

The 12,000-square-foot co-op on the 14th floor of 209 East Lake Shore Drive sold for $625 per-square-foot. The sprawling penthouse is a combination of two units Farley bought decades ago. The penthouse had been on the market since 2022.

Compass agent Jeff Lowe represented the seller, and Katherine Malkin, also of Compass, represented the buyer. They declined to comment on the buyer, and the buyer’s identity hasn’t been determined through public records.

The sale comes as downtown Chicago is struggling to find its footing after years of weak demand and falling prices. Sellers like the Farleys have had to cut their asking prices, sometimes by millions of dollars to find buyers.

But interest is starting to come back to downtown and condos can find buyers if they’re priced right. Lowe said the unit went under contract fairly quickly once it hit its last $7.9 million asking price.

That interest was reinforced in early December when billionaire Citadel founder Ken Griffin’s 67th–floor condo at 800 North Michigan Avenue went under contract with a buyer, with an asking price of $12.5 million. The deal hasn’t closed yet, but if it closes at the asking price it would be the most expensive sale for a single condo in downtown Chicago in at least three years.

Zach Lavine leaves No. 9 Walton

Zach LaVine was another downtown seller to take a loss last month. The former Chicago Bulls star sold his lavish condo at 9 West Walton Street for $6.4 million, taking a half-million dollar loss on the sale.

LaVine, who was traded to the Sacramento Kings in February, bought the 28th-floor condo from former Chicago Bears linebacker Khalil Mack for $6.9 million in 2022. The 4,500-square-foot unit, which features a 750-square-foot wraparound terrace and a custom tub with a built-in champagne bucket, is the latest turnover in a building that has become a hot spot for some of the most high-profile Chicago residents.

Griffin also took a loss at the building in the last year. He sold off the top four floors of the building last year after making his exit from Chicago for Miami, and two of those units were bought by Gov. J.B. Pritzker.

Former Blackhawks star Patrick Kane also sold his 25th-floor condo there for $6.4 million earlier this year.