These days, two topics are dominating cocktail-party chatter in the southwest Florida coastal city of Naples. When will the tony Port Royal Club reopen following its multiyear renovation, and who paid $311 million for nearly 19 acres of prime waterfront property on coveted Gordon Drive?For more than a year, the identity of the Gordon Drive buyer has been cloaked in secrecy, shielded by a land trust and strict nondisclosure agreements.For more than a year, the identity of the Gordon Drive buyer has been cloaked in secrecy, shielded by a land trust and strict nondisclosure agreements.

The buyer assembled the estate in two transactions, first paying Canada’s DeGroote family $225 million for 15 acres last year, then, 14 months later, buying the property next door from Ralph and Shelly Stayer for $86 million. Even real-estate agent Michael McCumber of Waterfront Realty Group, who brokered the deals, claims he doesn’t know who the buyer is. “They’ve never set foot on the property that I know of,” McCumber said. “It was always through representatives.”Chart 1The $311 million buying spree created one of the country’s most expensive compounds, putting the mystery buyer in rarefied company.

Citadel’s Ken Griffin has spent more than $450 million amassing a 27-acre compound in Palm Beach, while Amazon’s Jeff Bezos paid more than $230 million for multiple properties on Miami’s Indian Creek Island.But the secretive assemblage also speaks to the massive wealth pouring into Naples, which has long been in the shadow of Palm Beach and other affluent real-estate markets. Naples has recently seen a string of sales above $50 million amid fierce competition for waterfront estates, many coming to market for the first time in decades.

The Gordon Drive property was on the market at the same time as a compound down the street, also listed for $295 million. That left Naples agents scrambling to lure not one but two ultrarich buyers to the city.“It was unprecedented,” said Richard Prebish of William Raveis Real Estate, who brought potential buyers to both homes. “To see one of those as an offering is a once-in-a-lifetime opportunity for a prospective buyer, and here you had two.”Fifth Avenue South in Naples.Billionaires’ RowKnown for white-sand beaches and world-class golf, Naples has long attracted quiet money from the Midwest and Canada.

Historically, buyers were drawn to the city’s understated, almost sleepy feel compared with the flash of Miami and Palm Beach. “Naples is, ‘I’m a billionaire and I don’t want you to know about it,’” said real-estate agent Tim Savage of Gulf Coast International Properties.Chart 2Gordon Drive, a roughly 2.5-mile long stretch at the southern tip of a peninsula in Port Royal, is considered the Billionaires’ Row of Naples, with homeowners including Chicago hot dog mogul Dick Portillo and John Schnatter, founder of pizza chain Papa Johns.More than $1 billion in real estate has changed hands on the street since 2020, including three homes that sold for more than $50 million this year, according to a Wall Street Journal analysis of sales data. Of 49 Gordon Drive sales recorded since 2020, the average price was $21.2 million, compared with an average of $13.7 million for sales recorded since the 1980s.A gated entrance to the former DeGroote estate is shown in 2025.In an era of $100 million home sales, the $225 million transaction on Gordon Drive—which later grew to $311 million—was just the third deal in the U.S. to cross the $200 million mark.Two whalesFor decades, two families controlled large stretches of land on Gordon Drive.

Both estates were assembled in the 1980s by family patriarchs: Belgium-born businessman Michael DeGroote, who made a fortune building one of North America’s biggest trucking companies, and John Donahue, a West Point graduate who co-founded the Pittsburgh-based investment-management firm Federated Investors, now known as Federated Hermes.Michael DeGroote was personally involved in designing his Naples vacation home. “I was there for every sprinkler installation,” he said in a biographical film. The DeGroote family didn’t respond to requests for comment.About 2 miles away, John Donahue and his wife, Rhodora Donahue, were amassing some 50 acres, where they built a family compound for their 13 children and 84 grandchildren.

After John died in 2017, the Donahues sold around 40 acres for $41 million, leaving Rhodora with the remaining three houses and a yacht basin, according to Mark Murtha, president of the Beechwood Company, the Donahues’ family office.In 2022, both Michael DeGroote and Rhodora Donahue died, and their heirs prepared to sell.The DeGroote property went first, hitting the market in March 2023. The family didn’t want to break up the compound, so listing agent McCumber knew he needed to find a singular buyer—a whale.Representatives of a billionaire family made three separate offers over a nine-month period, McCumber said.

But 2023—sandwiched between Hurricane Ian in 2022 and the 2024 U.S. presidential election—was “the worst year possible to sell a property,” he said.By early 2024, there was competition from the Donahue property, which had hit the market as well.The DeGroote listing “had no bearing” on the Donahues’ decision to sell, said Murtha. The family had always intended to take advantage of price appreciation in Naples, he said.

The DeGroote property, however, did influence pricing.“Of course you take into consideration, when you’re listing any property—let alone that property—what your comparables are,” said Dawn McKenna of Coldwell Banker Realty, one of the previous listing agents for the Donahue property.The two families were also vying for attention from the same buyers. Most individuals who looked at the DeGroote property looked at the Donahue property, and vice versa, agents said. “There’s only so many…billionaires in the world right now,” Murtha said.The onetime DeGroote estate as seen from the road in April 2025.Both properties had aging homes that would likely be torn down by a new owner.

But while the Donahue property was surrounded by water on three sides, the DeGroote property was significantly larger and more private.In April 2025, a billionaire opted for space and seclusion, paying $225 million for the DeGroote property.The Donahue family had two reactions to the sale, Murtha said, including: “Maybe that could have been our buyer.” But they also felt it legitimized their asking price. “It set the bar higher for Naples,” he said. The family has since swapped brokers, hiring Savage, and relisting the compound for a combined $271 million.

The property is also being offered in smaller parcels to appeal to more buyers.Last year’s tax bill for the property was more than $1 million, records show, but Murtha said the family is patient. “Yes, we would like to sell,” he said. “But the phone call could come tomorrow.”The Donahue property, known as Gordon Pointe, has a yacht basin and dock.Behind the land trustAs of early October, the former DeGroote home was being razed behind a chain-link fence.As demolition began, McCumber figured that the Stayers, who owned the property next door, might want to sell. The Stayers, who declined to comment, are owners of Wisconsin-based sausage company Johnsonville and hold a stake in the Milwaukee Brewers baseball team.

McCumber had sold them their 3.73-acre estate in 2012 for $42 million.McCumber called the Stayers, asking them: “When do you want to sell this thing?” After they agreed the timing was right, McCumber contacted representatives for the owner of the former DeGroote property with a proposition: “You don’t need another piece, but will you be mad if someone else builds a mansion next to your home?” The tactic worked. Using the same land trust, the buyer purchased the Stayer property in June.Despite the astronomical sum, locals said they believe the $311 million assemblage is a harbinger of things to come in Naples.In 2025, investor David Hoffmann paid more than $100 million for neighboring properties in Port Royal. “I never thought I’d say this,” Hoffmann said, but “I am very comfortable with that price.” He said he never plans to sell, but should he have to, he is convinced he would make money.Meanwhile, the new Naples Beach Club, a Four Seasons Resort, opened last year.

And the luxury market was particularly busy this summer thanks to buyers anticipating the imminent reopening of the Port Royal Club, which was damaged in Hurricane Ian. Prebish said he notched $346 million in closed and pending sales from June to mid-October, more than triple the $112 million he did in the same period of last year. “The excitement is palpable,” he said.Write to E.B.

Solomont at eb.solomont@wsj.comStay updated with US News covering politics, crime, weather, local events, and sports highlights. Get the latest on Donald Trump and American politics along with Horoscope 2026.