What is most expensive home ever sold in America? $295 million listing in Port Royal, Florida

Located in an “exclusive neighborhood” known as Port Royal, the home has its own first and last name: Gordon Pointe. The nine-acre compound holds one primary home and two guest houses; altogether there are 20 bedrooms, 20 bathrooms (and four half-bathrooms), a 231-foot yacht basin, a 111-foot floating dock—and, can’t neglect to mention, 1,655 feet of waterfront. 

Courtesy of Dawn McKenna Group/Coldwell Banker Realty

It was smaller when John Donahue purchased it for $1 million in the 1980s after seeing the strip of land when (according to family stories) he was flying above it. At the time, it was a little more than four acres and had nothing on it apart from a fishing cottage, the Journal reported. The family built it over the next decade or so as they bought more land, and now after Donahue and his wife, Rhodora, passed away, their 13 children are selling. 

“We’ve all enjoyed it, but it’s more or less time to move on,” their son Bill Donahue, who runs the family’s foundation, told the Journal. His parents were high school sweethearts and devout Catholics; his father graduated from West Point in 1946, served in the Air Force, and started an investment management firm that’s now known as Federated Hermes (and run by another son). 

Their family grew from 13 children to 84 grandchildren to more than 175 great-grandchildren over the years, and the neighborhood transformed into one stuffed with business leaders and millionaires. Bill Donahue told the Journal that former President George H.W. Bush and American golfer Arnold Palmer were some of the well-known guests invited over.

The asking price suggests a new record for most expensive home sold in U.S. history. The current record holder belongs to the billionaire CEO of the massive hedge fund Citadel, Ken Griffin, who bought a penthouse on Billionaires’ Row in Manhattan for almost $240 million back in 2019. Others have come close but dropped their asking price as time went on. One of them, a Los Angeles mansion (deemed Casa Encantada) sitting on more than eight acres of land with seven bedrooms and 20 bathrooms, was originally listed for $250 million last year but is now going for $195 million. 

It’s quite an ask for the home marketed by Coldwell Banker Realty’s Dawn McKenna, Corcoran’s Leighton Candler, and Savills’ Rory McMullen given the pandemic-housing boom is over and this is a very different, chillier, housing market—one where existing-home sales fell to their lowest point in nearly 30 years, and luxury home sales declined almost 45% in a three-month period. But it could have a good chance of fetching that price, since home prices haven’t declined hand in hand with sales activity. By the fourth quarter of last year, luxury home prices were hitting all-time highs, driven by all-cash bids. A home in Miami sold for $79 million, for instance. 

The family wants to sell it as is, in one piece, rather than breaking it up. “If we were to break up the components, no one would put it back together again,” Donahue said, although one of the agents, Candler, told the Journal that the property can accommodate six houses, if not more. “We did our best to price [Gordon Pointe] and we can defend that price all day long,” one of the co-listing agents, McKenna of Coldwell Banker Realty, told CNBC.

Courtesy of Dawn McKenna Group/Coldwell Banker Realty

Clearly, this is a very different home than the norm, making comparisons difficult if not impossible. The average home value in Naples is close to $600,000, while its ritzy Port Royal neighborhood, with just 10,000 residents, has a median home sale price of slightly more than $9 million. (The relatively small number of transactions skews this data, as Port Royal’s sale price saw a 57% fall year over year, and Gordon Pointe’s eventual sale could blow that number out of the water.)

But who knows what will happen or who the magic buyer will be, because a large part of what makes Port Royal so appealing is its secrecy. As McKenna told the Journal, “Some of the wealthiest billionaires have places there, and you don’t know it.”