In Naples, Florida, a $295 million home for sale is currently the most expensive in the U.S.

• In Port Royal, Naples, Florida, lies the approximately 9-acre Gordon Pointe, a compound situated in an affluent neighborhood.
• The private peninsula houses a main house measuring approximately 11,500 square feet.
• Despite a potentially high asking price, the listing is already generating considerable interest, as reported by a co-listing agent.

This week, the priciest home for sale in the U.S. was listed at $295 million.

The roughly 9-acre compound in Naples, Florida, on the Gulf Coast, is known as Gordon Pointe, situated in the affluent enclave of Port Royal.

The estate boasts a main house of 11,500 square feet with six bedrooms, two guest houses of over 5,000 square feet each, and a total interior living space of 22,800 square feet. All three homes are situated on a peninsula that offers 1,650 feet of waterfront, a private yacht basin, and a T-shaped dock.

Leighton Candler of Corcoran, a co-listing agent, informed CNBC that the value of the three grand homes on the property is not primarily based on their size, but rather on the privacy, beach frontage, and the opportunity for significant development.

The property has the potential to accommodate more than 200,000 square feet of residential development, according to a press release that launched the listing.

Candler informed CNBC that the property could have up to eight waterfront homes, but he speculates that a potential buyer would likely keep it as a private family compound rather than breaking it apart after purchase.

John Donahue, co-founder of Federated Hermes, purchased the first of nine contiguous acres in 1985, with the firm now managing over $758 billion in assets.

The Donahues bought up the entire peninsula after their first purchase in 1985, creating an exclusive, gated compound almost entirely surrounded by water. With a single private drive, they enjoy no through traffic.

Candler stated that Gordon Pointe offers the advantages of an island retreat, but with seclusion for your family without feelings of isolation.

The Donahues constructed a 231-foot by 50-foot private yacht basin with a depth of almost 8 feet, which is a rare amenity that had to be approved by the U.S. Army Corps of Engineers, along with a T-shaped dock that can accommodate six boats.

Can Gordon Pointe fetch $295 million?

The median listing price in Port Royal, as per Realtor.com, is $24.1 million.

In December, the most expensive home in the ultra luxe beachfront community, priced at $45 million or $4,299 per square foot, was listed before Gordon Pointe. Meanwhile, an empty lot of 1.5 acres adjacent to Gordon Pointe has been on the market for a year, with an asking price of $63 million.

Co-listing agent Dawn McKenna of Coldwell Banker Realty stated on CNBC that they put in their utmost effort to determine the price of Gordon Pointe and can confidently defend it.

Since its launch on Wednesday, the listing has attracted substantial interest, resulting in eight scheduled in-person meetings with pre-approved buyers, as stated by McKenna.

It is not surprising for brokers to argue that a high price tag is justified, but true comparisons at this level are rare, and buyers with enough cash to pay that amount are few and far between. Additionally, there is often a significant difference between a property's initial asking price and its final selling price.

The second and third most expensive homes currently for sale in America are priced at nine figures.

In September 2022, a penthouse made its debut in New York City.

The three-story, 17,500-square-foot residence is situated on the 217 West 57th Street, providing a panoramic view of Central Park.

At the time, CNBC reported that broker Ryan Serhant listed the mega-apartment for $250 million, which he believed was a fair price.

Serhant stated in 2022 that the apartment, despite appearing expensive, is priced reasonably on a per-square-foot basis. He emphasized that it is a massive apartment with numerous amenities.

The high cost of the property was questioned by skeptics, with a price tag of over $14,000 per square foot.

In 2022, CNBC reported that Manhattan luxury broker Donna Olshan deemed the price "fantasy."

The $250 million triplex residence remained unsold for 12 months, prompting a $55 million price reduction, or 22%. Now, the luxurious property is still available for purchase at $195 million.

In Los Angeles, the journey was similar to that of Casa Encantada, a seven-bedroom, 20-bath mansion.

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

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

The home was removed from the market after the sky-high ask failed to attract a buyer, but it was later relisted in November with a $55 million price reduction.

Kurt Rappaport is still seeking a buyer for the $195 million property.

Nine-figure whisper sales

It can take months or even years for nine-figure listings to sell, and this does not necessarily indicate a broker's incompetence.

Jonathan Miller, president of Miller Samuel, examined 10 U.S. homes that sold for $150 million or more and discovered many of them were "whisper listings," which utilized clandestine word-of-mouth advertising and no public real estate listings or advertising campaigns.

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

Numerous well-known billionaires have been 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 acquired nine-figure compounds through private, off-market transactions.

One of the 10 transactions compiled by Miller's mega-mansion was officially listed for sale and has a unique price history.

The Chartwell Estate, a mansion located at 750 Bel Air Road in Los Angeles, had a $350 million price tag in 2017. Despite being on the market, it did not receive any offers, prompting a reduction in the asking price to $195 million.

In 2019, the estate was sold for $150 million to Lachlan Murdoch, the executive chair and CEO of Fox Corp., who is also the son of media mogul Rupert Murdoch.

Another notable transaction was the sale of a Malibu mansion at 27712 Pacific Coast Highway, which was never publicly listed but was reportedly worth $295 million.

In 2023, Jay-Z and Beyoncé purchased the company for $190 million in an off-market deal.