The most expensive home for sale in the U.S. goes up for $295 million in Naples, Florida

The main house at Gordon Pointe spans 11,500 sq ft.

The most expensive home for sale in the U.S. hit the market this week for $295 million.

Gordon Pointe, as it's called, is a roughly 9-acre compound in Naples, Florida, on the Gulf Coast, in an affluent enclave called Port Royal.

The mega-listing includes a main house that spans about 11,500 square feet, with six bedrooms. Two guest houses, each over 5,000 square feet, bring the estate's total interior living space to 22,800 square feet. All three homes are on a peninsula that delivers 1,650 feet of waterfront, a private yacht basin and T-shaped dock.

Before you start counting up bedrooms and calculating the price per square foot (which is about $12,900), co-listing agent Leighton Candler of Corcoran told CNBC the value here isn't so much about the size of the three grand homes on the property, it's about privacy, beach frontage and a rare opportunity for significant development.

According to a press release that launched the listing, “The property can accommodate more than 200,000 square feet of residential development,” meaning the land has a ton of untapped potential.

“There can be eight waterfront homes on this property,” Candler told CNBC. While the property could be broken apart after purchase, the New York-based broker speculates a potential buyer will more likely maintain it as a private family compound.

Gordon Pointe's sandy white beach stretches over 700 feet on the Gulf of Mexico.

The nine acres are made up of contiguous lots, the first of them purchased in 1985 by John and Rhodora Donahue. John Donahue co-founded a Pittsburgh-based investment management firm, now known as Federated Hermes, with over $758 billion in assets under management, according to the firm's website.

The waterfront view of the main house and a stretch of beach on Gordon Pointe.

After that first purchase in 1985, the Donahues continued to buy up more of the peninsula and didn't stop until they owned it all. Their buying spree created an exclusive, gated compound almost entirely surrounded by water. A single private drive means no pesky through traffic.

“It gives you all the benefits of being on an island, but on Gordon Pointe your family can be secluded without feeling isolated,” Candler said.

Along with a T-shaped dock that can accommodate six boats, the Donahues also constructed a private yacht basin that's 231 feet by 50 feet and has a depth of almost 8 feet. Candler told CNBC it's a rare amenity that had to be approved by the U.S. Army Corps of Engineers.

A view of Gordon Pointe with the private yacht basin in the lower right corner.Dawn McKenna Group / Coldwell Banker Realty

Can Gordon Pointe fetch $295 million?

According to Realtor.com the median listing price in Port Royal is $24.1 million.

The highest-priced home, before Gordon Pointe, in the ultra luxe beachfront community hit the market in December at $45 million, or just under $4,300 per square foot. Meanwhile an empty lot of almost 1.5 acres adjacent to Gordon Pointe has been on the market for a year, at an asking price of $63 million.

“We did our best to price [Gordon Pointe] and we can defend that price all day long,” co-listing agent Dawn McKenna of Coldwell Banker Realty told CNBC.

McKenna said the listing is already drawing significant interest since it went live Wednesday and that she's already booked eight in-person visits with prequalified buyers.

It's no surprise to hear listing brokers argue an eye-popping price tag is justified, but true comparisons at this level and buyers with enough cash to pay that kind of money are few and far between. And, as is the case with any real estate listing, there can be a big gap between an initial asking price and what a property ultimately sells for.

For some nine-figure context, here's a closer look at the second- and third-most-expensive listings currently for sale in America.

A view of the Central Park Tower at 217 West 57th St. in New York City.Source: Cody Boone, SERHANT Studios

The first of the two listings is a penthouse that debuted in New York City in September 2022.

The residence sits high atop 217 West 57th Street, overlooking Central Park, spanning three floors and over 17,500 square feet.

Broker Ryan Serhant made headlines when he listed the mega-apartment at $250 million, which he told CNBC at the time was the appropriate price.

“I know it sounds crazy, but relatively speaking, it's priced at a great value on a per-square-foot basis,” Serhant said in 2022. “It's just a very, very big apartment with lots of amenities.”

But naysayers questioned the nosebleed asking price, which amounted to over $14,000 a square foot.

“I consider this a fantasy price,” Manhattan luxury broker Donna Olshan told CNBC in 2022.

The triplex residence sat on the market for 12 months with no takers. After a yearlong run at $250 million, the asking price was slashed by $55 million, or 22%. The pricey pad is still on the market for $195 million.

Inside the $250 million penthouse on 'Billionaires' Row'

It was a similar journey in Los Angeles, with the seven-bedroom 20-bath mansion known as Casa Encantada.

The mansion, located at 10644 Bellagio Road in Bel Air, is owned by children's book author Karen Winnick, the widow of late billionaire and financier Gary Winnick.

The residence hit the market in June for $250 million.

After the sky-high ask failed to lure a buyer, the home was taken off the market only to reappear in November with a $55 million price cut.

Listing agent Kurt Rappaport is still looking for a buyer willing to pay the $195 million.

Nine-figure whisper sales

The reality is nine-figure listings can take months, even years, to sell, and that's not necessarily a reflection of a broker's ability.

Real estate consultant Jonathan Miller, president of Miller Samuel, looked at 10 U.S. home sales that traded for $150 million or more and found many of them were so-called whisper listings — sales that leveraged hushed word-of-mouth marketing and no public real estate listings or marketing campaigns.

That makes tracking price changes over the life of the listings nearly impossible.

Jeff Bezos gives a thumbs-up as he speaks during an event about Blue Origin's space exploration plans in Washington, D.C., May 9, 2019.Clodagh Kilcoyne | Reuters

But perhaps unsurprisingly there are a lot of famous billionaires involved in these sales, including hedge funder Ken Griffin, Amazon founder Jeff Bezos, Oracle co-founder Larry Ellison and mega-investor Marc Andreessen, who each picked up nine-figure compounds in quiet off-market deals.

The Chartwell Estate in Los AngelesPhotograph by Jim Bartsch, courtesy of the Estate of Jerry Perenchio

One notable mega-mansion of the 10 transactions compiled by Miller did officially come to market and has an interesting price history.

In 2017 the mansion at 750 Bel Air Road in Los Angeles, known as the Chartwell Estate, had a $350 million price tag. It sat on the market with no bites, and the oversized asking price took several deep cuts, to $195 million.

In 2019 the estate finally sold for $150 million, purchased by Lachlan Murdoch, executive chair and CEO of Fox Corp. and son of media mogul Rupert Murdoch.

Take a look inside of Lachlan Murdoch's new $150 million LA mansion

And another interesting mega-transaction made the list: A Malibu mansion located at 27712 Pacific Coast Highway. While it never actually had a public listing, The Wall Street Journal reported its whispered price tag was $295 million.

When it sold in 2023 in an off-market deal to music power couple Jay-Z and Beyoncé, it went for $190 million.