Originally listed at $50 million, the Lincoln Park mansion has spent years on the market and taken four price cuts
Tim Salm with Jameson Sotheby’s and 1932 North Burling Street in Chicago (Getty, Google Maps, Jameson Sotheby’s)
How many price cuts will Chicago’s most expensive listing need before it finds a buyer? 
As of last week, at least four.
The owners of the city’s most expensive listing, a custom home in Lincoln Park that cost over $65 million to build, have cut the home’s price again, this time to $23.5 million, potentially gearing up for a more aggressive sales pitch leading up to the end of the year and the coming spring market.
Owners Richard and Michaela Parrillo are moving to Florida to live there full-time. Tim Salm with Jameson Sotheby’s International Realty is listing the property and did not respond to a request for comment.
The home was initially listed for sale at $50 million, and subsequent price cuts brought the listing down to $45 million and then $30 million. In September, the ask was chopped again to $27 million before this month’s trim.
The $23.5 million asking price pulls the home more closely into the orbit of Chicago’s most expensive residential real estate deals in the last several years, making a potential sale more likely. It would also mark a loss of $41.5 million from what the owners said they initially paid to acquire the lots and build the home.
This year, with climbing interest rates and an overall slowing luxury market, major sales have been much less frequent than prior years.
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In 2022, Chicago had two $20 million residential sales.  Those properties were the sale of the penthouse at Trump Tower for $20 million and the sale of the penthouse at the St. Regis for $20.6 million. So far this year, though, the biggest sale of the year so far in Chicagoland has been for a $12.5 million mansion in Winnetka.
The Burling Street home’s time on the market shows the upper limits of Chicago’s residential real estate market, where top-of-the-line homes sell for considerably less than their equivalents in New York, Los Angeles or Miami.
The Parrillos bought the eight city lots on Burling Street in 2016. Richard, founder and CEO of Florida-based United Auto Insurance, said the project wasn’t supposed to be so grand, but it was a “labor of love” for his wife, so its cost increased over time.
The six-bedroom home also has a speakeasy bar area and a 5,000-bottle wine cellar and tasting room modeled after a building at Versailles.
Despite the price cut, the home is still the highest priced listing on the market, with few other listings coming close. Those include a $22 million suburban estate listing in Lake Bluff that was designed by David Adler and a $15.7 million home in the Gold Coast.
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