City’s most famous mansion sellers bought Gold Coast penthouse

Less than a year after making headlines for the record-breaking sale of their Lincoln Park mansion, Richard and Michaela Parrillo have settled into a new home. In July, the couple purchased a 6,800-square-foot penthouse on the Gold Coast in the Ambassador Hotel building at 1300 N. State Parkway for $6.5 million, according to public records.

The two-story condo spans the 39th and 40th floors. With five bedrooms, six bathrooms, and sweeping views of downtown from the 1,400-square-foot private rooftop terrace with gardens and outdoor entertaining space, the home was a steal. At $956 per square foot, it came at a steep discount from its 2015 sale price of $6.9 million. The unit had lingered on the market for several months, undergoing several price cuts, dropping from $8 million in 2022 to $7 million earlier this year, before the Parrillos purchased it.

The Ambassador Hotel, built in 1918, is famous for its guest appearance in the 1959 Alfred Hitchcock film “North by Northwest.” In 1959, Queen Elizabeth and Prince Philip are said to have attended a luncheon hosted by Gov. William G. Stratton in the building. In the early 2000s, the hotel was converted into a 37-unit boutique luxury condo building housing some of Chicago’s famous residents and the socially elite. 

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For the Parrillos, the move represents both a downsizing and a dramatic shift in lifestyle. Their previous residence, the now-famous Burling Street estate in Lincoln Park, was anything but modest. At 25,000 square feet on eight city lots, it was once Chicago’s most ostentatious private home.

Designed by architect Thomas Beeby, the limestone-clad mansion featured a 22-karat-gold repoussé staircase, a 5,000-bottle wine cellar modeled after the Great Stable of Versailles, and a rotunda entry of French marble. Outside, gardens and fountains framed a hand-forged pavilion and a reflection pool.

When construction began in 2006, the couple spared no expense. “Construction of the house at a cost of about $40 million got away from me, but it’s a labor of love for my wife,” Richard Parrillo told Crain’s in 2008. By the time the dust settled, the Parrillos had spent an estimated $65 million on land and construction.

Despite the grandeur, the mansion proved a tough sell. First listed in 2016 for $50 million, it lingered on the market for years, dropping to $23.5 million before finally closing in August 2024 for $15.25 million.

The sale set a record for Chicago’s most expensive single-family home transaction. Yet financially, it was a loss for the Parrillos. As Crain’s pointed out, the $12.5 million they paid for the land in 2005 equaled about $20 million in 2024 dollars, meaning the mansion sold for less than the adjusted land value.

The buyers, revealed as developer David Cocagne and his wife, attorney Manasi Bhattacharyya Cocagne, stepped into a bargain-priced palace.

Tim Salm of Jameson Sotheby’s International Realty represented the Parrillos in both transactions, the sale of Burling Street and the purchase of the State Parkway condo.

Although the couple left behind a property that symbolized excess and extravagance, their new home reflects a quieter, if still luxurious, urban lifestyle. Trading in a 25,000-square-foot palace for a 6,800-square-foot penthouse might feel like downsizing, but in the world of Chicago real estate, the Parrillos remain firmly in the upper tier.