Florida’s most expensive real estate listing is back on the market for $271million – after eye-watering $24million dollar price cut

Florida’s most expensive real estate listing has returned to the market for a cool $271 million, down from an earlier asking price of $295 million. 

Known as Gordon Pointe, the ultra-exclusive waterfront estate sits at the southern tip of Gordon Drive in Naples’ prestigious Port Royal neighborhood, where Naples Bay meets the Gulf of Mexico.

The estate covers roughly nine acres, including an extraordinary 722 feet of Gulf of Mexico beach frontage and a 231-foot private yacht basin.

The $24 million reduction from the original asking price makes the property one of the most eye-catching luxury listings in America – and a reminder that even the country’s most expensive homes are not immune to a little reality checking.

Gordon Pointe first hit the market in 2024 for $295 million, making it the most expensive residential listing in the US at the time.

It subsequently came off the market, before recently relisting with the $271 million price tag.

The stunning estate includes the main house, two smaller additional homes and the yacht basin. 

The property is listed by Tim Savage of Gulf Coast International Properties.

And while $271 million is still an eye-watering sum, the buyer is getting something that would be almost impossible to recreate.

The estate occupies the tip of Gordon Drive, surrounded by water and offering both Gulf sunsets and views across Naples Bay.

Its position provides direct access to the Gulf of Mexico without bridges, a particularly valuable feature for owners with large boats. The property has a fascinating family history, too.

Financier John ‘Jack’ Donahue, co-founder of Federated Investors, now known as Federated Hermes, and his wife Rhodora began assembling the compound in 1985 after purchasing an initial four-acre waterfront parcel for around $1 million.

Over the following decades, the couple expanded their holdings, eventually creating a sprawling estate that grew to approximately nine acres.

The Donahues raised 13 children at Gordon Pointe, turning what could have been a showpiece for one family into a multigenerational home.

Jack Donahue died at the property in 2017, while Rhodora died around five years later. Their estate has since decided to sell part of the compound.

The current property includes an approximately 11,500-square-foot main residence with six bedrooms, along with two guest houses. 

Inside, the homes feature details including cathedral ceilings, built-in cabinetry and concrete floors, although the real star of the show is arguably outside.

The waterfront setting provides spectacular views in almost every direction, while the private basin and dock offer an exceptionally rare amenity for a Naples property.

The estate also offers enough development potential for more than 200,000 square feet of additional residential construction.

And the property’s location places it firmly in one of the most exclusive corners of Naples.

Port Royal is known for its enormous waterfront homes, private streets and deep-water access, while owners can also be eligible for resident membership at the Port Royal Club, which recently completed a $100 million reconstruction of its private beach club.

It is also less than four miles from Naples’ famous Third Street South and Fifth Avenue South shopping and dining areas, while Naples Executive Airport is roughly seven miles away. 

The area has seen some eye-popping deals in recent years as wealthy buyers compete for scarce waterfront land.

In 2025, three neighboring properties on Gordon Drive reportedly sold for a combined $225 million, underlining just how much money is changing hands along the exclusive stretch.