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Choice Neighborhood: Keewaydin

Forests, beaches and privacy make for one desirable refuge.

With miles of secluded beaches and loads of privacy from the rest of Southwest Florida, Keewaydin has become a haven for the wealthy.


A desire to relax in the seclusion of subtropical forests with nearby beaches abundant with shells and neighbors who have profiles as high as their own have led many to seek refuge on Keewaydin Island. A 7-mile stretch of isolated land just south of Port Royal, the island, historically known as Kee Island, today quietly hosts celebrities of all sorts in the 25 or so homes that exist there.

Although many houses there have breathtaking views and beach frontage still offered for less than $3 million, let there be no mistake: Those who own homes or visit Keewaydin do not do so because of the fabulousness of the dwellings—most are simple stilt homes with moderate accoutrements.

“It’s paparazzi-proof,” explains Realtor Sherry Irvin, who sold property to Jim Biden, Vice President Joe Biden’s brother, two days before Christmas last year. For the Biden family, that means a highly secured house with property stretching from the backwaters of Rookery Bay to the Gulf, a home and a few outbuildings in the midst of 60 acres of protected forests. For other homeowners, a neighboring house may be visible over the treeptops. Still, a sense of privacy surrounds all.

Irvin, who calls herself “island girl,” reared two daughters for 10 years on nearby Little Marco, learning the lay of the land and the creatures that inhabit it. Almost daily, she paddled a kayak across the shallow water between the two islands to walk Keewaydin’s beaches.

“It’s kind of like a mantra of island living,” she says.

“You respect everyone’s privacy, but if you need someone, they’re here.”

But who is there? No one now lives on Keewaydin (or Little Marco) year-round other than a few caretakers, perhaps. The homeowners generally have a few other houses in other parts of the country or world, so their presence may be infrequent. Irvin says there’s a mix of music, Hollywood, tech and sports celebrities who come and go. Some can’t even get in—she once was unable to find a home for Jimmy Buffet to use for a week.

The founders of the famed Irish dance troupe, Riverdance, built a compound but have since sold it. The house of artist Donna Wheatley and her investment banker husband is for sale for $2.9 million—it was prefabricated and has more modern amenities than some of the others.

In most island homes, utility systems are rustic, too. Electricity comes from generators and solar panels. Water is cleansed or carried in. Huge propane tanks are delivered on a barge. Yet, cell and Wi-Fi are available.

Despite high-powered homeowners and guests, the isolation of Keewaydin hasn’t changed much from the time that local Realtor Phil Collins was a child. Every spring break, Collins traveled from Chicago to explore the island’s pathways, where his grandparents, Lester and Dellora Norris, owned a northend rustic camp known as the Keewaydin Club, the only location on the island where electricity has been installed.(Delnor-Wiggins Pass State Park is named for Collins’ grandmother. Both of his grandparents were active in local and preservation issues.)

“It was all basically a shell path,” Collins explains, regarding his days on Keewaydin. “A couple of golf carts and we got to enjoy a lot of boating, fishing and shelling.”

After 50 years of family ownership and granting some nonadjacent Keewaydin property to the State of Florida, Collins’ aunt and Naples resident Lavern Gaynor—who worked for two years to list the club on the National Register of Historic Places—sold the Keewaydin Club in the early 1980s. “I got stuck with it,” she says, remembering the hassles of overseeing the rustic resort after her parents’ deaths. By then it was a substantial operation, involving at least 15 buildings, multiple factions of family and friends who visited, staffing and a small marina near Port Royal.

The property was sold to the Drackett family, including Lucille Drackett and her late husband, Bolton. The Dracketts eventually sold some of the northend land, which then became part of the Rookery Bay National Estuarine Research Reserve.

A few years later, Port Royal resident Jack Donahue bought the remaining Keewaydin Club property and still owns it today. (By the way, Donahue’s company, Federated Investors, is a major contributor to Republican causes and candidates, making Keewaydin a politically balanced island.) Several of the club’s original buildings have since been demolished, although a portion of the original lodge is preserved in a newer structure. There are still no cars on the island, just golf carts, and most owners have boats to access their properties. If residents want to build anything—those lucky enough to find a piece of land—it’ll cost exponentially more than on the mainland. Irvin guesses it’s at least $600 a square foot.

While picking up shells along the beach, Irvin recalls Sept. 11, 2001, and the days that followed when she was living on Little Marco. During a national halt to air traffic, a hovering Marine One helicopter puzzled her. Then she heard rumors that Laura Bush was on Keewaydin.

A day on the water with Irvin and Jim Griesser, whose Keewaydin Property Management oversees 18 of the island’s homes, reveals other tales. Griesser and his crew spend more time on the island than most of the homeowners.

There’s a story about one of the island’s wild boars drunken on fermented coconut milk, another about dolphins mating on the beach.

No matter which property Griesser and his crew are managing, the wild backwaters of Rookery Bay as well as the pristine beaches of the Gulf of Mexico are just steps away.




Collier County


Naples No. 2 in “Top 10 Destinations for Vacation Rentals in 2013” (USA Today)

Naples No. 2 on “2012 America’s Happiest Seaside Towns” (Coastal Living)

Naples No. 7 on “100 Best Places to Retire for 2013” (topretirements.com)

Naples No. 4 on “Best Florida Beaches” (U.S. News & World Report: Travel)

Naples No. 9 on “The 20 Best Small Towns in America of 2012” (Smithsonian magazine)

Four golf communities (Estates at Bay Colony, Grey Oaks, Mediterra and Talis Park) in Naples made “America’s Top 100 Golf Communities” (TRAVEL +LEISURE GOLF)

Naples-Marco Island area No. 5 on list of fittest cities, from Gallup-Healthways Well-Being Index (Gallup)

Naples-Marco Island area No. 2 on “Cities with the Most Millionaires in America” (aneki.com)

Marco Island No. 4 in “Top 10 Destinations for vacation Rentals in 2013” (USA Today)

Marco Island No. 3 on safest places in Florida list (2012, Movoto Blog)

Marco Island No. 4 on “Top 10 Islands—World” (TripAdvisor)

Collier County No. 4 on “Best Places for a Long Life”—list of 25 counties (CNNMoney)


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