America’s Most Expensive Property Is Sitting in a Flood Zone—Will Anyone Buy the $295 Million Estate?

Who would spend more than a quarter of a billion dollars on a property guaranteed to flood in the near future? That question has remained unanswered since February, when the most expensive home in America hit the market.

The Naples, FL, property—listed for a staggering $295 million—comes with unparalleled amenities and 1,655 feet of water frontage on three sides. That access to prime waterside real estate might tempt many billionaires, who may or may not care that the home sits in one of the nation’s most at-risk areas for climate-related disasters.

The climate risk rating on the Realtor.com® listing page is “Severe,” rated 7 out of 10 for the risk of flooding. The Flood Factor™ states: “This property has a 95.60% risk of flooding over 30 years. This property’s risk of flood is increasing as weather patterns change. Flooding in this area is caused by precipitation, sea level rise, and hurricane storm surge.”

Realtor.com economist Joel Berner says that “the top end of the market has been slumping all over the country and especially in Florida.

“Buyers are very price-conscious, and with better access to environmental risk data through our Dynamic Map Layers, they’ll be able to assess the risks of buying flood-prone properties like this one that are properly priced,” he notes.

However, that might not matter to some buyers.

“Florida continues to have a lot of appeal for the uber-wealthy because there is no state income tax, and many people continue to flock there for this reason, irrespective of insurance costs, and live in very expensive homes on or close to the water,” says Cara Ameer, a real estate professional in Ponte Vedra, FL.

As for the Naples property, Ameer adds: “You essentially have your own private island here, and the long marketing time may simply be due to aspirational pricing for a unique property, which can take time to find the buyer audience for this home.”

The history of 100 Bay Road

Known as Gordon Pointe, this jaw-dropping waterfront estate spans 9 acres. This palatial property includes a grand main residence and two guesthouses, all with sweeping views of the Gulf of Mexico. Boating enthusiasts will be impressed by the private yacht basin, T-shaped dock, and extraordinary 1,655 feet of water frontage.

But the story behind this estate is just as impressive as the property itself. Financier John Donahue snagged the original 4-acre parcel in 1985 for just $1 million—a steal by today’s standards, according to the Wall Street Journal. By 1989, he’d built his family’s dream home, then kept adding to it, turning a single lot into a sprawling coastal haven that’s become one of the area’s crown jewels.

“This property is in a different stratosphere, and when you are talking $300 million, the property has to be just right for a potential buyer for all sorts of reasons,” says Ameer. “The seller of something like this doesn’t ‘have’ to sell, nor does a buyer ‘have’ to buy, and a buyer who can afford $300 million has a lot of options in many markets right now.”

Who will own it next?

Flooding might send most buyers running, but for the ultrawealthy, it’s just another solvable inconvenience.

“It is no secret that flooding and insurance risk are issues to consider when buying a property on or close to the water, no matter the price point,” says Ameer. “However, for someone that can afford to spend nearly $300 million to buy a private estate, the cost of insurance to protect the property is likely less of a concern because they can likely self-insure or will spend the money on insurance to protect what they can.”

Luxury real estate sales remain as hot as ever, along America’s coasts—places like Malibu, CA, and Palm Beach, FL, where rising sea levels and storms dominate headlines. In other words, billionaires aren’t balking.

The wealthy often sidestep hurricane season altogether, jetting off to other estates when the storm threat peaks. And when they do occupy these properties, they’re armed with every resource imaginable—even private emergency response teams.

Why put up with the risks at all? Because properties in these locations offer what no inland mansion can: sweeping ocean views, exclusive beach access, and proximity to cultural and entertainment hubs. For buyers with unlimited budgets, these irreplaceable perks make even flood zones worth the investment.

“And should something happen to the Naples property, the buyers could always sell it for land value, and there are many possibilities given the amount of land that this sits on for future development,” says Ameer.