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With 1,660 feet of prime waterfront real estate in Naples, Florida, and an extended family that included 13 kids, 84 grandchildren and 179 great grandkids, the Donahues faced some logistical challenges. “In the nineties, we would regularly have dinners with up to 100 people every Friday and Saturday night,” says Bill Donahue, one of the 13 children of the late financier John Donahue and his wife, Rhodora, whose sprawling Gordon Pointe compound made headlines earlier this year when it hit the market for a record-setting $295 million. During the family’s 40-year run at the property, Donahues from all over were constantly visting. “Everyone wanted to go to Gordon Pointe, but not everyone could go at the same time,” says Bill. “So we eventually had to create a reservation system.”

While perhaps the most famous modern-day example of an affluent, multigenerational family making large swaths of prime Naples waterfront their personal sandbox, the Donahues are far from alone. “The high-end luxury market in Naples is booming,” says Coldwell Banker’s Dawn McKenna, the listing broker for Gordon Pointe. Median sales across Naples have surged 13.8% year over year, according to Rocket Mortgage sister company Rocket Homes, and McKenna says the spike is even more pronounced in affluent areas, such as Old Naples, Aqualane Shores and Port Royal. Today, she adds, a “teardown” in Aqualane Shores, an upscale waterfront neighborhood with deep-water channels and canals, fetches $5 million to $6.5 million. And if you want new construction in this sought-after neighborhood, expect to pay $14 million to $25 million, she says. “You can’t even get a lot for $10 million in Port Royal.”

Gordon Pointe | Photography provided by Dawn McKenna | Coldwell Banker Realty | Three Palms Media

Nestled along the pristine shores of the Gulf of Mexico, Naples has long been sought after for its white-sand beaches, world-class golf courses and vibrant cultural scene. However, the recent surge in luxury-property sales has catapulted the city to the forefront of the global real estate arena. “Everyone’s saying that Naples has been undervalued for a long time,” says Ashley Baird Fenttiman, another Coldwell Banker broker. She and McKenna are currently trying to sell a six-bedroom, eight-bathroom, 7,689-square-foot beachfront property that’s within walking distance from downtown Old Naples for nearly $43 million. Demand for these massive waterfront homes currently outstrips supply, Fenttiman says. “For most of the sellers, these are third, fourth or fifth family homes, so none of them really need to sell.”

She predicts that the values will continue to climb in coming years as downtown Naples undergoes a shiny new makeover. In October 2023, a local developer sold 27 downtown properties to an Aspen, Colorado–based developer for $300 million. “It’s all retail and office space around Fifth and Third, so they have the opportunity to completely reimagine the retail spaces,” says Fenttiman. She predicts the new downtown could eventually rival Worth Avenue in Palm Beach as a luxury shopping destination.

Aqualane Shores | Photography provided by Dawn McKenna | Coldwell Banker Realty | Three Palms Media

Bill Wheeler, a developer who recently built a $17 million home in Aqualane Shores, says Naples’s calm Gulf beach makes it extremely family-friendly: “The Gulf of Mexico is warm, swimmable and shallow, so it’s great for kids — and grandkids! The water on the ocean in Palm Beach is much rougher and deeper.”

In Naples, Wheeler says, it’s also easier to find waterfront property than it is on the East Coast: “Palm Beach and Naples have many homes right on the ocean, but Naples also has many properties with little inlets and canals where you can stash your boat in the backyard and be out on the water in minutes.”

That is exactly what the Donahue clan did for over 40 years at Gordon Pointe. “Growing up, we’d hop on our boat and be in the Gulf of Mexico in less than five minutes,” says Bill Donahue. The original 4.3-acre beach area, which the elder Donahue purchased for just $1 million in 1985, eventually mushroomed to roughly 60 acres, where the family built a seaside playground, complete with three houses and a private yacht basin.

So what does one get for nearly $300 million in Naples? In addition to the 11,500-square-foot main house with six bedrooms and a screened-in pool, the Donahues added a 5,500-square-foot guest house in 1990 with five bedrooms and an outdoor pool. This is where George and Barbara Bush stayed when the Donahues threw one of their legendary bashes for Bush’s son Jeb, who was running for governor at the time. “We call the room [the former president] stayed in the presidential suite,” says Bill, noting that Bush was “very friendly and loved to fish.”

Aqualane Shores | Photography provided by Dawn McKenna | Coldwell Banker Realty | Three Palms Media

In 2013, the Donahues added a 5,800-square-foot second guest house, which looks out onto an outdoor pool and a T-shaped dock that can accommodate six boats. “I always loved watching the sunset, trying to see if we could catch the famous ‘green flash,’” says Bill. A transient meteorological optical phenomenon that occasionally occurs as the sun disappears into the ocean, the elusive, brief green flash enchanted multiple generations of Donahues. “I only witnessed it once,” says Bill.

Other highlights of the Donohues’ years in Naples include giant fetes for Arnold Palmer and various other famous golfers, along with visits from notable bishops and cardinals, epic Easter egg hunts and festive Halloween parties. “There were always hundreds of people coming and going,” says Donahue. “My mom was a great hostess.”

So what made the Donahue family finally decide to sell this seaside Shangri-la? John Donahue passed away seven years ago, Rhodora a year and a half ago. Of their 13 children, 11 now own their own properties in Naples. Even with the reservation system, Bill says, “it got to the point where we were getting so big as a family that it was hard to manage, and it seemed like it was time to let someone else enjoy Gordon Pointe. Hopefully, it will remain a big family gathering compound, and they’ll use it for 40 years like we did.”

Read this article as it appears in the magazine.

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