Billionaire Portillo’s founder lists Naples penthouse for $33M


Dick Portillo, known to many as the king of the Chicago hot dog and the Italian beef sandwich, is serving up a chance to live like a royal in Naples, Florida.

The Chicago-born founder of the Portillo’s restaurant chain, which has stores throughout Chicagoland, as well as in Wisconsin, Florida and Texas, listed his recently remodeled Naples penthouse for $32.5 million. If the unit sells at its asking price, it would set a record closing for a Naples condo resale, according to MLS data cited by its listing agents Bill Earls and Larry Lappin.

Earls and Lappin of John R. Wood Christie’s International Real Estate put the home on the market late last month. The five-bed, seven-bath condo spans nearly 12,000 square feet within the 43-unit building called The Seasons at Naples Cay, at 81 Seagate Drive.

The penthouse was built in 2002 and last sold for $11 million in September of 2022. It was recently redesigned by Portillo with the help of C&E Builders and Theory Design’s Ruta Menaghlazi; it’s unclear how much Portillo and his team invested in the overhaul.

The residence features floor-to-ceiling glass windows with panoramic views of the Gulf of Mexico and the city of Naples, the listing said. Among the amenities are four guest suites, a sauna and exercise room.

Portillo remains a real estate player in Chicagoland. Described as a self-made billionaire, he sold the Portillo’s restaurant chain and its real estate in a deal reportedly worth $1 billion in 2014. Later that year, he paid $74 million to buy back 18 of the chain’s properties in the Chicago area and collect the rent from the leases brought in by them.

Portillo’s involvement in the Naples listing was disclosed just a day after another luxury Naples property owned by the family of late financier John Donahue went up for sale at a record price of $295 million. That 9-acre property, known as Gordon Pointe, was listed by Chicago-based agent Dawn McKenna of Coldwell Banker Realty.

Unless it sells for drastically below the asking price, the Gordon Pointe estate will likely set a new national record for priciest residential sale, surpassing billionaire Ken Griffin’s $238 million purchase of a Manhattan penthouse in 2019.



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