Chicago’s Most-Expensive Home Sales of 2024

This year’s top Chicago home sales show significant price growth in the city’s ultra-luxury market over last year, as the top three sales of 2024 all surpassed last year’s priciest sale.

The list also shows the challenges of serving clients at the top of the market as brokers navigated high interest rates, low inventory levels in hot submarkets like the North Shore and shifts in demand away from downtown condos. Though the ceiling of Chicago’s ultra-luxury market pushed higher this year, the number of sellers trading at a loss increased as well.

This year’s top two sales came at major losses to the sellers who, after years of trying to sell, bit the bullet and took losses of $33.65 million and $50 million rather than continuing to wait. Four others on the list (Nos. 3, 4, 7 and 9) also sold at large discounts or losses to the sellers.

Further price growth is projected in the new year, and a few potential contenders for priciest sale of 2025 have already emerged. A $21 million home on North Astor Street in Gold Coast hit the market in October; Ken Griffin’s Park Tower penthouse is listed for $15.75 million; and Jena Radnay of @properties is privately marketing a $35 million lakefront estate in Winnetka set to list soon. In the western suburbs, a 70-acre Barrington Hills estate was listed for $22 million.

For the biggest home sales of 2024, TRD Data analyzed public listing information from Cook County, collected earlier this month, to find the market’s most-expensive deals.

While Chicago’s top residential deals showed a rebound in luxury prices from 2023 lows, the ultra-luxury market still has not quite returned to 2022 levels when multiple $20 million-plus sales hit an exceptionally strong year for residential real estate.

9 West Walton Street, Penthouse 37 and 38, Chicago | $19 million

This year’s priciest sale came when Illinois Gov. J.B. Pritzker bought two full-floor penthouses at the No. 9 Walton building downtown from his long-time political rival — Citadel’s Ken Griffin — for a combined $19 million in November. The sale came at a $14.65 million loss for Griffin, who purchased the two unfinished floors in 2017 for $33.65 million.

Griffin purchased the two floors along with the buildings’ 35th and 36th floors — which are also unfinished — in a deal totaling over $58 million. He put the 36th floor unit on the market this fall at $8.5 million, priced to lose at least $3.63 million. The Citadel founder moved his company to Florida two years ago and has been pushing to sell off his Chicago properties for years now, taking significant losses on some properties.

Though they sold at a loss, the combined sale of the two No. 9 Walton penthouses to Pritzker was also the fourth-priciest sale of all-time in Chicago as of December.

The 37th and 38th floors fetched $9 million and $10 million, respectively, and each span 7,500 square feet. The 38th floor has a private rooftop pool and sold for just over $1,300 per square foot, while the 37th floor sold for $1,200 per square foot. Nancy Tassone of Jameson Sotheby’s International Realty and Emily Sachs Wong of @properties Christie’s International Real Estate represented Griffin, and Compass’ Katherine Malkin represented Pritzker, who bought the property through an LLC.

1932 North Burling Street, Chicago | $15.25 million

Chicago’s second-priciest sale this year also came at a major loss to the sellers, this time to the tune of $50 million, after the estate at 1932 North Burling Street in Lincoln Park spent years on the market. Ultimately, the 25,000-square-foot home sold to an undisclosed buyer for $15.25 million, or $610 per square foot.

Engel & Volkers’ Jennifer Ames represented the buyers, who are locals and plan to live in the house. The sellers, United Automobile Insurance Company Chairman and CEO Richard Parrillo and his wife, Michaela, were represented by Jameson Sotheby’s International Realty’s Tim Salm and Matt Leutheuser. The Parrillos sold the home for 30 percent of its initial asking price and roughly 65 percent of its last listing price. They spent about $65 million acquiring the land and building the six-bedroom, 11-bathroom house in 2010.

400 West Dickens Avenue, Chicago | $14.25 million

Next up was a 15,000-square-foot mansion on Dickens Avenue in Lincoln Park that sold for $14.25 million or $950 per square foot. The home was previously listed at $15 million, priced just below the nearby North Burling Street estate that ranked as Chicago’s second-priciest sale, and went under contract for $14.25 million just a few weeks after hitting the market. The sellers, Chicago Trading Company executive Paul Kepes and his wife, Monica, previously disclosed they spent $20 million to buy the land and build the property, meaning they also sold at a loss of about $5.75 million. The sellers were represented by Salm and Ryan Preuett of Jameson Sotheby’s International Realty. Susan Miner of Premiere Relocation represented the buyers, who could not be identified by public records.

65 East Goethe Street, 8N, Chicago | $9.3 million

At the start of the year, Chicago Trading Company Co-founder Andrew Hall sold off his eighth-floor Gold Coast condo for $9.3 million. That’s about $1,033 per square foot for the 9,000-square-foot unit, and is 33 percent below the asking price of $13.9 million when the condo hit the market in March of last year. Hall purchased the unit before it was finished for $6.7 million from former Wrigley Company chairman Bill Wrigley in 2011. Hall was represented by Jennifer Mills of Jameson Sotheby’s International Realty and Compass agent Mark Icuss represented the buyer.

Just a few weeks into January, Hall’s condo sale was already the fifth residential sale in the city over $4 million.

50 Beach Road, Glencoe | $8.2 million

There was also an uptick in off-market sales this year as demand tightened in the Chicago area’s hottest luxury markets like Lincoln Park and the North Shore. This lakefront mansion in Glencoe, for example, traded hands for $8.2 million in an off-market deal in January. That’s about $851 per square foot for the 9,600-square-foot home at 50 Beach Road. The buyers weren’t identified.

660 Prospect Avenue, Winnetka | $8.1 million

Chicagoland’s priciest deals are often taking place on the North Shore, with three of the top 10 home sales falling along the lakefront just north of the city limits. In Winnetka, this 7,800-square-foot Georgian Rival mansion sold this summer for $8.1 million, or $1,039 per square foot, according to property records and public listing information. The six-bedroom, six-bathroom lakefront home features a pool and cabana. The seller was represented by Radnay of @properties Christie’s International Real Estate.

1500 North Lake Shore Drive, Penthouse, Chicago | $7.7 million

This two-story Gold Coast penthouse sold at a 45 percent discount from its 2020 asking price of $17 million. The historic penthouse at 1500 North Lake Shore Drive was acquired this summer by an anonymous buyer for $7.7 million or $962 per square foot. The unit spans the 24th and 25th floors of the 1920 co-op building designed by architect Rosario Candela in collaboration with McNally & Quinn. Colette Cachey Smithburg of @properties Christie’s International Real Estate represented the buyer, while the seller, the late Michael Wilkie, was represented by Salm of Jameson Sotheby’s International Realty.

21 North May Street, Unit 1501, Chicago | $7.56 million

This year also cemented West Loop and Fulton Market as important areas for high-end residential real estate. The Embry, Sulo Development’s 16-story, 58-unit condo project in West Loop, opened to residents in late 2023 and already had 81 percent of its units under contract with buyers by the end of last year. This 15th floor penthouse at The Embry sold in May of this year for $7.56 million, or $1,457 per square foot, landing the West Loop condo building a spot among Chicago’s top home sales. The four-bedroom, 5-bathroom home spans over 5,100 square feet with 2,300 square feet of patio space. The building’s sales are managed by Compass’ Mark Icuss as well as Tim Sheahan, whose work at The Embry earned him in the No. 4 spot on The Real Deal’s ranking of Chicago’s top brokers this year.

9 West Walton Street, 1901, Chicago | $7.3 million

Another condo at the No. 9 Walton building downtown made the top 10 when it sold to an undisclosed buyer this August for $7.3 million, or $1,403 per square foot. The 19th-floor unit once belonged to Major League Baseball player Jason Heyward, a former Chicago Cubs outfielder who now plays for the Houston Astros. Susan Miner of Premier Relocation represented the sellers and buyers in the transaction.

595 Longwood Avenue, Glencoe | $7.25 million

The sale of this Glencoe estate was a loss for the sellers but, at the time, it also marked the town’s priciest sale since December of 2021, though the sale on Beach Road ultimately topped it. The 8,800-square-foot home sold for $7.25 million or $826 per square foot — just over half of its 2022 asking price of $13.8 million, or $1,572 per square foot. The seven-bedroom mansion at 595 Longwood Avenue sits on 1.68 acres and boasts 132 feet of Lake Michigan shoreline. Laura Rubin Dresner of Baird & Warner represented the sellers, David and Susan Kalt, while Beth Wexler of @properties Christie’s International Real Estate represented the buyers, who were not identified.