Mystery solved? Public records point to owner of $36 million Port Royal mansion

Laura Layden
Naples Daily News

The mystery has been solved.

Or so, it appears, based on public records.

A notice of commencement recorded in Collier County Circuit Court points to a Chicago billionaire as the mystery buyer who paid $36 million for a mansion in Naples. 

The notice for roof repair at the posh Port Royal abode — sitting at 2750 Gordon Drive — is signed by private equity investor Justin Ishbia, using the title "owner."

By the way, subscribers:

This Naples home at 2750 Gordon Drive is one of the most expensive to ever sell in the city, with a price tag of $36 million.

Forbes ranks Ishbia as one of America's richest people. He's one of the 20 wealthiest people in Illinois, with a net worth of more than $3 billion.

The Chicago Tribune first dug up the public notice, as it looked to uncover the mystery buyer for the Naples estate — and a 3.3-acre home site in Winnetka, an affluent village about 20 miles north of Chicago.

The same legal entity appeared as the mystery buyer for the Winnetka and Naples properties in public documents: Orchard 2020 Revocable Trust.

The home site on Lake Michigan fetched $23.9 million, making it the highest sum ever paid for a single-family residential property in the Chicago area, beating the former record held by Groupon co-founder Eric Lefkofsky, who paid $19.5 million for a Glencoe mansion in 2014, the Tribune reported.

The trustee for Orchard 2020 is Peter Lee, a partner in and founder of Summit Trail Advisors, a Chicago-based financial advisory firm that specializes in serving entrepreneurs, private equity partners, entertainers and professional athletes (think NFL, NBA and NHL).

2750 Gordon Drive, Naples

Previously, Lee declined to comment about his client's purchase of prime waterfront real estate in Port Royal — recognized as one of the priciest neighborhoods in America. He could not immediately be reached for this story.

More recently, Lee disputed in an interview with the Chicago Tribune that Ishbia purchased the Naples mansion, contradicting the information filed in Collier County Circuit Court.

“That’s not accurate. It was filed in error. … I just want to let you know that document is not accurate," he told the reporter who writes Elite Street, a weekly column covering luxury and celebrity home sales throughout Chicagoland.

Ishbia did not respond to a request for comment by the Chicago Tribune or the Naples Daily News.

Mat Ishbia and his dad, Jeff Ishbia on Dec 2, 2016 at the UWM holiday party; Nelly was a special guest performer at COBO.

According to Forbes, Justin Ishbia is an investor in Michigan-based mortgage lender United Wholesale Mortgage, founded by his father, Jeff, in 1986. He owns a 22% stake in the company, which went public through a merger with "a blank check company" in January 2021.

Launched as "a side gig while Jeff worked as an attorney for his day job," Forbes reports the mortgage company grew to become one of  America's largest wholesale lenders in 2015.

Justin's brother, Mat — a former college basketball player turned billionaire — serves as the mortgage company's CEO. According to Forbes, his net worth tops more than $10 billion.

CEO Mat Ishbia of United Wholesale Mortgage rang the opening bell on Jan. 22, 2021.

While he's in the family business, Forbes reports Justin's "main focus" is on his Chicago-based private equity firm Shore Capital Partners.

Local Realtor Bill Earls, a specialist in the luxury market who represented the seller of the Naples mansion, known as "La Capana," couldn't immediately be reached about the revelation of its secretive buyer. 

In the description for the property on his website, Earls labeled the estate as "one of the most significant beachfront residences ever created in Naples."

The sprawling estate spans 18,172 square feet. Special features include a five-car "collectors" garage and a 500-bottle wine room.

Did you know?:In the Know: Naples named 'best beach town' in USA

Built in 1999, the Italian Renaissance-style palace, with more than a half-dozen bedrooms, includes marble floors and a fireplace, along with a beachside game room, his and hers studies, a two-story rotunda, an elevator and a mahogany bar topped with green marble. 

Previous owner Robert A. Watson sold the property through his own revocable trust. He's a former president and chief executive officer of units of Westinghouse and TransAmerica.

Watson spent $3.5 million to renovate and expand the home before putting it up for sale.

This Naples home at 2750 Gordon Drive is one of the most expensive to ever sell in the city, with a price tag of $36 million.

As for the property in Winnetka, The Chicago Tribune reports a building permit for the home that will go on it has not been filed, so the plans are still a mystery.

According to the daily newspaper, Ishbia assembled the land through two trusts. 

The plan for assembling the property didn't come easy, as it included a rather complicated land swap with the Winnetka Park District.

The exchange gave the district 8 acres of uninterrupted parkland, with about 1,000 feet of uninterrupted shoreline that will not only improve public access to Lake Michigan, but also help preserve the shoreline and bluff, said John Peterson, the district's executive director, in an interview with the Daily News earlier this year.

The village honored the true buyer's wishes to remain private, but word still got out.

The Chicago Tribune reports Ishbia is "no stranger to high-end residential real estate in Chicago," having doled out more than $5.5 million for a 30th-floor condominium in the city through a Delaware limited liability company in 2018.

Back in Naples, the price Orchard 2020 paid for the gulf-front mansion in Port Royal didn't quite set a record in the city known as a playground for the rich.

However, it still ranks as one of the highest residential sales in about three years in Southwest Florida, according to Matt Simmons, a principal of real estate appraisal firm Maxwell, Hendry & Simmons.

"It can be very difficult to sell a property like this," he said in a recent interview. "The pool of buyers is very small and the marketing efforts need to be surgical."

In late January, a stately family compound at 2700 Gordon Drive in Port Royal, set a new all-time record for the most expensive home ever sold in Naples, fetching $52 million.

It's a stone's throw away from what public records say is Ishbia's new home.

Daily News reporter and In-the-Know columnist Phil Fernandez contributed to this story.