Chicago’s most-expensive listing finds a buyer, once priced $50M 

Chicago’s most expensive home on the market, a Lincoln Park mansion that was first listed for $50 million back in 2016, has found a buyer. 

After multiple price cuts, the Lincoln Park mansion last listed at $23.5 million is under contract with an unidentified buyer, the Chicago Tribune reported. This is the first time in the eight years the home has been on the market that its sellers have struck up a contract with a buyer. The home’s sale price remains unknown.

The six-bed, 11-bath home, at 1932 North Burlington Street, is owned by United Automobile Insurance Company Chairman and CEO Richard Parrillo and his wife, Michaela, and has been on and off the market since 2016. 

After two years on the market, the home was removed and relisted in 2019 with the price cut down to $45 million. This price still far exceeded the next most-expensive listing at the time — a Gold Coast mansion owned by Pete’s Fresh Market owner Jimmy Dremonas that was seeking $22 million. 

The lavish Lincoln Park palace remained the city’s most-expensive listing through multiple more price reductions, including a $20 million chop that brought it down to 60 percent of the original price in January of last year. 

The home’s square footage, and value, has come into question. 

In 2023, the Cook County Assessor stated that the Parrillos’ mansion had a fair market value of $16.2 million and a square footage of just over 15,500 square feet, the outlet reported. But the mansion was last listed at $23.5 million, and listing information gives a square footage of 25,000. 

Tim Salm of Jameson Sotheby’s International Realty has the listing. 

The limestone home has a 2,000-square-foot wraparound terrace and comes with a gated motor court, decorative fountains, a pavilion and reflection pool. There is also an attached three-car garage.

The Parrillos bought the Lincoln Park site from the Infant Welfare Society in 2005 for $12.5 million. The custom-built mansion spans eight city lots. One of the home’s former listing agents told Elite Street that the cost of building it was $65 million, including land costs.

If so, the Parrillos stand to lose tens of millions on the home, which they have owned for nearly two decades. 

—Kelli Duncan

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