The most significant residential offering in the United States. Nearly nine acres at the tip of Gordon Drive, where the Gulf of Mexico meets Naples Bay. Listed at $271 million.
At the very tip of Gordon Drive, where the sheltered waters of Naples Bay open into the vast blue of the Gulf of Mexico, sits a property that has no peer in American residential real estate. Gordon Pointe is not simply a home for sale. It is a peninsula - a private landmass that commands both sunrise bay views and sunset Gulf panoramas, wrapped in the kind of seclusion that simply does not exist anymore.
The estate occupies a singular position within Port Royal, Naples' most prestigious gated community. Situated at the convergence of Gordon Pass, the Gulf, and the bay, the property offers something no other listing in the country can claim: nearly nine acres of contiguous waterfront with over 1,600 combined feet of frontage, a private yacht basin exceeding 200 feet in length, and a T-shaped dock that accommodates up to six vessels.
Gordon Pointe was shaped by the vision of John "Jack" Donahue, the co-founder of Federated Investors (now Federated Hermes), and his wife Rhodora. High school sweethearts from Pittsburgh, they first acquired a parcel here in 1985 for $1 million. Over the next three decades, they assembled what would become one of the most expansive private compounds in all of Florida - approximately 60 acres within Port Royal's guarded gates.
The Donahues raised 13 children at Gordon Pointe. Jack passed away on the property in 2017; Rhodora followed roughly five years later. Their estate now encompasses more than 80 grandchildren, and the family has made the decision to offer a portion of the compound to its next steward - someone who shares their reverence for privacy, coastal preservation, and the kind of legacy that outlasts any single generation.
Gordon Pointe is not just a property - it's a legacy of vision, love, and respect for the natural beauty of Naples.
Tim Savage, Principal - Gulf Coast International PropertiesThe compound currently includes a main residence of approximately 11,500 square feet with six bedrooms, along with two guest houses added in 1990 and 2013 respectively. But the structures are almost beside the point. What makes Gordon Pointe irreplaceable is the land itself - its position, its scale, and the impossibility of ever assembling anything like it again. The property is listed exclusively by Tim Savage of Gulf Coast International Properties.
Over 700 feet of private beachfront on the Gulf of Mexico, far removed from the nearest public access point. Uninterrupted sunset views across open water.
Nearly 950 feet along Naples Bay with sweeping views of Gordon Pass and the daily parade of yachts, sailboats, and sport fishers heading to open water.
A sheltered basin exceeding 200 feet in length with a 111-foot T-dock capable of berthing up to six vessels. Direct Gulf access with no bridges.
The estate can accommodate over 200,000 square feet of additional residential construction - ideal for a family compound, a single mega-estate, or several world-class home sites.
Property owners at Gordon Pointe are eligible for resident membership at the Port Royal Club, which recently completed a $100 million reconstruction of its private beach club - a project that has further elevated the neighborhood's position at the very top of the American luxury market.
Gordon Pointe's listing arrives at a moment when Port Royal is producing transactions that would have been unimaginable even five years ago. In 2025, three adjacent waterfront properties on Gordon Drive sold for a combined $225 million - roughly 15 acres with 800 feet of Gulf frontage. Individual sales along the corridor now routinely exceed $40 million, and the area's transformation into one of America's premier wealth enclaves continues to accelerate.
The migration of high-net-worth individuals to Naples' Gulf Coast has been well documented. What is less often discussed is the structural supply constraint that makes Gordon Drive properties so extraordinary: there will never be more waterfront land here. Every parcel that trades is one fewer that will ever come to market again. Gordon Pointe, by virtue of its scale and its position at the peninsula's tip, represents the most significant of these irreplaceable assets.
Gordon Pointe anchors the southern end of one of the most valuable residential corridors in the world. The stretch of Gordon Drive south of Cutlass Cove represents the pinnacle of Port Royal - larger lots, wider Gulf frontage, deeper water access, and the kind of end-of-the-road privacy that cannot be manufactured.
Several significant properties along this corridor are currently available or have recently traded, ranging from vacant beachfront parcels with preliminary architectural plans to fully built Gulf-front estates. For qualified buyers exploring this segment of the market, early access and discreet representation are essential - many of these opportunities never reach the MLS or are available only through private, off-market channels.
This is the market our team knows best. With 14 years in Naples and a network that reaches into every pocket of Port Royal's ownership community, we routinely surface properties before they're publicly listed. Whether you're considering Gordon Drive, the wider Port Royal market, or exploring Naples' other premier neighborhoods, a confidential conversation is the first step.
We provide confidential, off-market access to Port Royal's most significant properties - including estates that never appear on the MLS. Start with a private conversation.