Chicago 'hot dog king' lists 3 Naples properties for $58.6M

The founder of the famed Portillo’s restaurant chain has partnered with a Southwest Florida builder on three luxury properties — units he is now selling through a prominent real estate broker with ties to both Chicago and Naples.

The properties are all in Naples and include an 11,698-square-foot penthouse priced at $27.9 million; a 6,500-square-foot house priced at $16.99 million; and a 5,000-square-foot house priced at $13.75 million.

Dawn McKenna who runs Coldwell Banker Realty’s Dawn McKenna Group has been hired to sell the properties. 

McKenna is a well-known Chicago-area broker who has offices in Naples as well as New Buffalo, Michigan; Park City, Utah; and Lake Geneva, Wisconsin.

According to Coldwell Banker, in 2023 her group saw more than $590 million in transactions.

Among her sales is the Chicago-area house featured in the classic holiday movie “Home Alone.” It sold last month for $5.5 million.

The three Naples residences are a partnership between C&E Builders and Dick Portillo, once described in a newspaper headline as “Chicago’s hot dog king.”

Portillo founded the popular Portillo’s restaurant chain outside Chicago in 1963 and grew it to 38 locations before selling the chain to Berkshire Partners in 2014 after it had expanded nationally.

Today, the chain, known for its Chicago-style hot dogs, Italian beef sandwiches and burgers, operates 90 restaurants across 10 states. Of those, eight are in Florida, including four in the Tampa Bay market.

(Coldwell Banker, which announced the listing of the three homes, requested that the Business Observer refer to Portillo as a “celebrated founder of a highly successful restaurant empire” in this story and not to mention his connection to Portillo’s.)

Portillo first joined up with C&E, the Naples builder, in 2021.That’s when Chris Covelli and Ed Kellerman bought the construction company that renovated Portillo’s condominium and built his Port Royal home, according to Coldwell Banker.

The former restauranteur proposed they partner up to co-develop future spec projects. Together they formed P&C Real Estate Development.

“My decades in the business world have taught me how to spot those rare, like-minded people who will only accept excellence,” Portillo says in the statement. “And when you find it, partner with these individuals to accomplish great things together.”

In addition to the three residences, the portfolio McKenna is charged with selling includes a fourth property built by C&E for a separated development team. The 4,4470-square-foot house is at 1645 Bonita Court. It sits on .31 acres and has 82 feet of waterfront. It is priced at $8.9 million.