Chicagoland’s priciest home sales of 2023

Top of the market was nowhere close to record-setting $20M-plus sales last year, but plenty of head-turning closings took place

Chicago’s Top Residential Sales of 2023
691 Sheridan Road and 445 Sheridan Road in Winnetka with @properties Jena Radnay and 800 North Michigan Avenue with Ken Griffin (VHT, @properties, Getty, Redfin)

Chicago’s luxury residential market in 2023 amounted to a considerable drop from previous years with both the highest priced sales and overall deal volume.

However, it’s shown signs of life recently: Sales at or above $4 million were still plentiful. 

More could be on the horizon for early 2024. Multiple luxury homes are under contract or listed as contingent on public listing sites.

That includes what could likely be a contender for 2024’s priciest sale, if it closes at or near its listing price. A 73rd-floor condo at JDL’s One Chicago, at 14 West Superior Street, has been under contract for nearly all of 2023. Listed in January at nearly $14 million, it went under contract within three days, but has yet to close.

For the biggest home sales of 2023, TRD Data analyzed information from Cook County as well as Redfin, collected earlier this month, to find the market’s most expensive deals.

It’s been a challenging year for Chicago’s residential market overall, with low inventory and high interest rates slowing down sales that had been booming since the pandemic.

This year’s list is noticeably different from the 2022 list. Two $20 million-plus sales hit last year, setting records. With this year’s sluggish market, the top of the list reverted to pre-pandemic levels.

691 Sheridan Road, Winnetka | $12.5M

The priciest sale in Cook County happened outside of Chicago, another change from last year. The 12,500-square-foot home in Winnetka sold for $1,000 per square foot. The five-bedroom, seven-bathroom home was built in 2005 and sits on Lake Michigan beachfront. Jena Radnay with @properties Christie’s International Real Estate represented the sellers, and Edward Gobbo with Berkshire Hathaway HomeServices Chicago represented the buyers: protein bar company RxBar co-founder Jared Smith and his wife Gabriella. The sale marks a 39 percent decrease from the previous year’s top spot: the $20.6 million sale of a penthouse at the St. Regis.

445 Sheridan Road, Winnetka | $12.25M

The second-priciest home is also in Winnetka, also on Sheridan Road, and was also listed by Radnay. The 6,000-square-foot home, sold for over $2,000 per square foot, was built in 1918 and sits on over 2 acres on Lake Michigan. The home was designed with old-school entertaining in mind and originally included a ballroom. The property includes an elevator, speakeasy-style cocktail bar in the basement, and a sauna. The property also has a two-story cabana with its own elevator, a custom bar and two full kitchens. The sellers were business executive Randy Abrahams, who listed the property for $15.85 million in September 2022. The buyers, whom Radnay also represented, were Shiraz and Vijay Kotte, who are both executives in healthcare-related fields.

800 North Michigan Avenue, Penthouse 66, Chicago | $11.2M

Shortly after Ken Griffin announced his plans to depart Chicago for Miami, he listed four of his trophy properties in the city. A penthouse on the 66th floor of Park Tower was the second of the properties owned by Illinois’ former wealthiest resident to sell. The property closed for $1,400 per square foot in January. It sold at a 25 percent loss for the billionaire founder of Citadel; he purchased the five-bedroom, 8,000-square-foot unit for $15 million in 2012. The home was listed by Susan Miner with Premier Relocation and Katherine Malkin of Compass represented the buyers.

1956 North Orchard Street, Chicago | $10.6M

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This Lincoln Park home sold for almost $964 per square foot after a $2 million cut to its asking price made in May. The seven-bedroom, 11,000-square-foot home was built in 2001 and renovated in 2020. The property was built on three city lots and includes a rare-for-the-city side yard. It features a three-story staircase atrium, a mud room, pet shower and outdoor half basketball court. It sold for $5.3 million in 2012 and was owned by Jennifer Dicke Prewitt and her husband, Andrew Prewitt. Dicke Prewitt is the daughter of James F. Dicke II, the chairman and CEO of Ohio-based Crown Equipment Corporation. The home was listed by Suzanne Gignilliat with @properties Christie’s International Real Estate, and Sharyl Mackey of Baird & Warner represented the buyer.

1100 North Lake Shore Drive, Unit 40B, Chicago | $6.8M

A penthouse on Lake Shore Drive once owned by Michael Jordan sold in an off-market deal for $850 per square foot in May. The condo was originally three units that were previously assembled into an 8,000-square-foot condo. The sellers were Jennifer McNeil Dhadwal and Amit Dhadwal. Amit Dhadwal is an executive at PayPal, and Jennifer Dhadwal is an executive at AECOM. The property was listed by Julie Busby and Pamela Moran of Compass, and Lisa Finks and Diana Radosta of Compass represented the buyer. Jordan purchased the condo during his time with the Chicago Bulls in the 1990s. His ex-wife, Juanita Vanoy Jordan, retained the condo after the two divorced in 2006. She sold it for $3.2 million in 2014. Michael Jordan still owns his ultra-custom home in Highland Park, which has been on the market since 2012 and is asking $14.85 million.

363 East Wacker Drive, #6306, Chicago | $6.5M

Sales in the St. Regis residential tower dominated 2022’s list of priciest residential deals. A $20.6 million penthouse set a record for the highest priced residential sale in Chicago. This year, with less inventory on the market, sales at the tower have been fewer and farther between, but this four-bedroom, 4,800-square-foot condo on the 63rd floor sold for a little over $1,350 per square foot in May. Leila Zammatta with Magellan Realty LLC represented the developer, and Danielle Dowell and Jaclyn Kelly with Berkshire Hathaway HomeServices Chicago represented the buyers.

54 East Scott Street, Chicago | $6.5M

A rare contemporary home in Chicago’s Gold Coast sold for $625 per square foot. The 10,400-square-foot, five-bedroom home was built in 2010. The home includes an elevator, private outdoor space, and an attached 5-car garage with a gated driveway. Engel & Voelkers broker Jenny Ames represented the seller, which was an LLC registered to Mark J. Ladd of Monarch Equities and his wife, Christiane Ebsworth Ladd. Mark Icuss with Compass represented the buyers, who were not identified in public records. It closed at a big price cut from the $9.4 million it originally sought when it hit the market in the spring of 2022.

2026 North Mohawk Street, Chicago | $6.3M

A home with ties to Ken Griffin’s ex-wife Anne Dias sold for $572 per square foot. Dias is the founder and CEO of New York-based investment firm Aragon Global Management. The 11,000-square-foot, seven bedroom Lincoln Park home was listed by Emily Sachs Wong of @properties Christie’s International Real Estate. Susan Miner with Premier Relocation represented the buyer.

451 East Grand Avenue, #5909, Chicago | $6.35M

This condo at One Bennett Park sold for about $1,270 per square foot over the summer, after less than a month on the market. Built in 2019, the 5,000-square-foot condo has four bedrooms and five bathrooms. Built by Related Companies, One Bennett Park is in the Streeterville neighborhood and has 69 stories. The condo was listed by Bradley Brondyke and R. Matt Leutheuser with Jameson Sotheby’s International Realty, and Elizabeth Ballis and Deborah Ballis Hirt of Compass represented the buyer.

325 Shoreline Court, Glencoe | $6.25M

This home, designed by architect Tony Grunsfeld and built in 1997, sold for a little over $1,000 per square foot. The 6,000-square-foot house is on Lake Michigan, with views of the lake throughout the home and 130 feet of lake frontage. The property once belonged to lawyer and crime novelist Scott Turow. It has had several owners since Turow, and the sellers this year were obscured in public records through a title company. Radnay of @properties Christie’s International Real Estate represented the buyers and sellers.

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