Florida's priciest residential listing, known as Gordon Pointe, has returned to the market with a reduced asking price of $271 million, marking a $24 million decrease from its initial listing earlier this year. The estate, located at the southern tip of Gordon Drive in Naples' Port Royal neighborhood, originally listed for $295 million, making it the most expensive home for sale in the U.S. at the time.
The property spans approximately nine acres and features 722 feet of Gulf of Mexico beach frontage and a 231-foot private yacht basin. The reduction in price highlights the adjustments occurring even in the ultra-luxury real estate market.
Gordon Pointe comprises a main residence of approximately 11,500 square feet with six bedrooms, along with two additional guest houses. Its waterfront position offers direct access to the Gulf of Mexico without bridge obstruction, a significant advantage for owners with large yachts. The estate is situated where Naples Bay meets the Gulf, providing panoramic views.
The property has a notable family history. Financier John 'Jack' Donahue, co-founder of Federated Investors, and his wife Rhodora began acquiring the land in 1985, eventually expanding their holdings to create the nine-acre compound. They raised their 13 children on the estate. Both passed away in recent years, and their estate is now selling a portion of the property.
The current listing covers 5.39 acres, a reduction from the original nine-acre compound, but retains extensive Gulf beach frontage. The estate's architecture includes features such as cathedral ceilings, built-in cabinetry, and concrete floors, though the exterior amenities are considered its primary draw.
Gordon Pointe is located in one of Naples' most exclusive areas, known for its large waterfront homes and deep-water access. Proximity to the Port Royal Club, Naples' Third Street South and Fifth Avenue South shopping and dining districts, and Naples Executive Airport are also key features. The area has seen significant high-value transactions, with three neighboring properties on Gordon Drive reportedly selling for a combined $225 million in 2025.