Gordon Pointe relists at $271M as Port Royal resets ceiling

Gordon Pointe, the Port Royal compound that is helping redefine the top end of the U.S. housing market, is back for sale in Naples, this time with a $271 million asking price.

The nearly 9-acre estate at 100 Bay Road sits at the tip of a peninsula near Gordon Pass, with frontage on both the Gulf and Naples Bay. When the relisting was announced, the price was not publicly disclosed because the offering was marketed “by invitation only,” Gulf Coast International Properties Chief Operating Officer Vicki Tracy said. She later confirmed the $271 million figure to Gulfshore Business.

Gordon Pointe’s return comes as Port Royal continues to produce transactions that would have seemed implausible in most U.S. markets even a few years ago. In 2025, three adjacent waterfront properties at 2170, 2200 and 2340 Gordon Drive sold for a combined $225 million, totaling about 15 acres with roughly 800 feet of direct Gulf frontage. The deal was brokered by Michael McCumber of The McCumber Group at Gulf Coast International Properties, and the scale of the sale became a shorthand for how far the local luxury market has stretched.

“Port Royal is undergoing a remarkable transformation, with the $100 million reconstruction of its private beach club driving a new era of luxury living,” McCumber said in April 2025.

The biggest component of that three-parcel transaction was 2200 Gordon Drive, an 8,846-square-foot estate with 11 bedrooms and 16 bathrooms.

A Redfin analysis of the nation’s top home sales in 2025 put 2200 Gordon Drive at the top of the U.S. market, followed by two Los Angeles estates that each sold for $110 million. The ranking underscored what local brokers and analysts have been arguing for years — that coastal Florida, and Naples in particular, now competes directly with the traditional high-water marks of California and New York for ultrawealthy buyers.

The momentum at the top end is also reflected in the broader luxury pricing structure. In December, the entry point for luxury homes in the Naples-Marco Island metro area — defined as the 90th percentile of listing prices — stood at $3.61 million, the seventh-highest level in the country, according to Realtor.com. The threshold was down 2.3% from a year earlier, but it still left Naples in a small tier of markets where luxury listings are priced at least five times higher than the local median.

“Big gaps between luxury and typical home prices aren't automatically a warning sign,” Realtor.com senior economist Anthony Smith said. “They often point to markets that are highly segmented, where luxury behaves differently from the rest of the housing market.”

In Naples, that segmentation has played out not only in beachfront estates but also in trophy bayfront property. In April 2025, billionaire entrepreneur David Hoffmann and his wife, Jerri, purchased a 17,202-square-foot Port Royal bayfront home at 575 Admiralty Parade W. for $85 million, according to officials with Gulf Coast International Properties. The sale was described as the highest price ever recorded for a single-family residence in Collier County’s history and the highest price for a nonbeachfront single-family home in the county, based on MLS data. The eight-bedroom, 10 1/2-bath home sits on 2 1/4 lots with 250 feet of Naples Bay frontage. The Agency’s Chris Resop and Gulf Coast International Properties Principal Tim Savage represented the seller.

Those benchmark deals form the context for Gordon Pointe, which has long been positioned as its own category of asset. The compound first made national news in early 2024 when it was listed for a record-breaking $295 million, then the highest asking price for a home in the U.S. If the estate had sold anywhere near that level, it would have threatened to surpass the national residential sales record set in 2019, when billionaire hedge fund manager Ken Griffin purchased a penthouse at 220 Central Park South in Manhattan for about $238 million, as reported by The Wall Street Journal.

The original marketing described three homes totaling about 22,800 square feet, with 728 feet of beach frontage and 927 feet of bay frontage, plus a private 231-foot yacht basin and a 111-foot T-dock — an infrastructure package that effectively turns a residential property into a private waterfront campus. For buyers who treat Naples as a primary residence, winter base or multigenerational destination, the combination of acreage, frontage and deepwater access has become increasingly difficult to replicate in Old Naples.

The listing has also evolved. In January 2025, the Donahue family reduced the asking price by $85 million to $210 million after deciding to keep pieces of the property that had been included in the original offering. The revised listing was later removed from the Southwest Florida MLS in August.

The estate was stewarded for decades by philanthropists John “Jack” Donahue, who died in 2017, and his wife, Rhodora, who died in 2022. Beginning in the 1980s, the couple assembled roughly 60 acres in Port Royal, with Gordon Pointe emerging as the centerpiece. According to The Wall Street Journal, the family hosted gatherings of more than 100 people at the property and entertained notable guests, including former President George H.W. Bush, former first lady Barbara Bush, former Florida Gov. Jeb Bush and clergy from the Catholic Church.

“Gordon Pointe is not just a property — it’s a legacy of vision, love, and respect for the natural beauty of Naples,” said Savage, the listing agent.

Bill Donahue, one of the heirs, previously described the decision to sell as a generational transition: “We’ve all enjoyed it, but it’s more or less time to move on,” he said.

As Port Royal continues to draw ultra-high-net-worth buyers and post record-setting closings — from the beachfront sale at 2200 Gordon Drive to the Hoffmanns’ $85 million bayfront purchase — Gordon Pointe’s $271 million relisting signals a market still willing to test the limits of what a single address can command.