The entrepreneur behind Chicago’s famous hot dog joint Portillo’s is teaming up with Florida-based C&E Builders and Chicago broker Dawn McKenna on luxury developments in Naples, Florida.
This is not Dick Portillo’s first development, as he’s spearheaded multiple commercial and residential developments in the Chicagoland area, but it is his first foray into luxury residential in the South Florida market — where prices are far beyond even the ultra-high-end of Chicago real estate.
The team is marketing the project to wealthy individuals and second homebuyers in Chicago and along the East Coast, Portillo and C&E Builders’ Chris Covelli said.
“The big markets we see are Chicago, New York, Boston — they’re still coming down here, and Naples is a very attractive place for them to land,” Covelli said. “There’s obviously tax incentives. And you’re still seeing, even in a slower market over the last few months, serious transactions occur, really, on a monthly or weekly basis.”
Chicago is one of the top cities that people move to Naples from, second only to Miami, according to Redfin. From October to December of last year, 1,446 Chicago residents moved to Naples — well above New York’s 866.
Covelli acquired C&E Builders with Ed Kellerman in 2021. Covelli and Portillo met shortly after, when C&E worked on Portillo’s home in the Port Royal neighborhood of Naples, and the two formed a development team called P&C Real Estate Development.
They are bringing single-family spec homes to the market, as well as a $27.9 million penthouse at The Seasons at Naples Cay condo complex, according to a news release.
The 11,700-square-foot penthouse at 81 Seagate Drive is the priciest of the team’s developments, at $27.9 million or almost $2,400 per square foot. They are also selling a 5,000-square-foot home at 349 2nd Avenue North, a few blocks from the beach, for more than $13.7 million, or $2,750 per square foot.

The offerings also include homes in Royal Harbor, at 1640 Dolphin Court and 1645 Bonita Court. The home on Dolphin Court is priced just under $16 million, or about $2,460 per square foot, and sits on Naples Bay. It is set to be completed in May.
The home on Bonita Court also borders Naples Bay and has the price most comparable to Chicago’s luxury market, at $8.9 million, which is under $2,000 per square foot. It was built by C&E Builders for a separate development team.
McKenna leads Coldwell Banker’s top-transacting broker team in Chicago and Naples. Her connections between the two markets give her an advantage in marketing the spec homes, Covelli and Portillo said.
The Dawn McKenna Group, which came in at No. 10 on The Real Deal’s ranking of Cook County’s top brokers last year, started off in Chicago’s western suburbs before opening an office in the city and then on the affluent North Shore, McKenna said. From there, she capitalized on her connections and made the jump into the Naples market.
“Everything that Naples is, Chicago is not — except for the people,” McKenna said. “People want to work with people they like and trust, and they want to simulate the lives they had, and their hometown, in another place.”
Her Chicago clients like the familiarity of the Naples community when offered together with favorable weather and more walkability, she said.
These wealthy buyers don’t just come from Chicago, but across the Midwest from Minnesota to Ohio, McKenna said. Early in her career, McKenna did “road shows” across the Midwest, talking to potential clients and other agents to spread the word about the “lifestyle” offered by Naples and other popular second home destinations she served.
“It really has created quite the ripple effect,” she said. “We saw the fruits of our labor in like two years … I didn’t even realize how big and how quickly that business would develop.”
McKenna said she was surprised by how much interest there was in Naples among Midwestern buyers even with the jump up to South Florida prices. Last year, McKenna made headlines when she helped list an extravagant Naples compound, owned by the family of late financier John Donahue for $295 million, making it the most expensive U.S. residence on the open market.
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