The drive out to the luxury community of Windsor, Florida, feels like passing through worlds. Asphalt unfurls relentlessly across the state’s swampy underbelly, past RV towns, cattle ranches, deactivated power plants, and unending rows of orange trees with workers harvesting fruit in the midday sun. Birds of prey circle down on blistered fields and the smell of wood smoke hangs in the humid air, even as Smokey the Bear insists, sign after sign, that fire levels are at a minimum.
Luxury rodeos and casino joints start cropping just east of Osceola County, where I’m greeted by the spectacular sight of Yeehaw Junction—a chaotic trucker spot just off the Florida Turnpike that looks exactly like it sounds. 18-wheelers piled high with citrus barrels cross the intersection, horns blaring, loose oranges falling akimbo. As the miles keep coming, Florida continues to oscillate between unfathomable affluence and destitute poverty.
On the bridge to Orchid Island, the McMansions emerge all at once. Orchid, the town next to Windsor, boasts the ninth highest income in America; it’s also the only town I’ve ever knowingly been to that is 100 percent white. All 450 of its residents must have been somewhere else that day (perhaps their real homes), because it seems completely empty.
Finally, the serif script sign announcing Windsor Club appears and I veer left into a grove of oak trees. I learn later that oak is a favorite motif of Hilary Weston, one half of the couple behind Windsor. The Westons’ Canadian empire dates back to the late 19th century, beginning with a bread factory that ballooned into an international food processing and distribution conglomerate; the couple now has a combined net worth in the billions. Just like Windsor’s host state, the Westons’ companies cover the whole socio-economic spectrum, ranging from luxury department store Selfridges to Primark, the U.K. equivalent of Walmart.
Founded in 1989, Windsor intends to “combine yesterday’s charm with modern comforts and the vision of tomorrow.” Having encountered the land in its elemental state—mangrove bushes straddling the ocean and dirt paths through overgrown forests—the Westons wanted to develop the future community of Windsor in a way that honored the intrinsic purity of the landscape.
They called upon Andrés Duany and Elizabeth Plater-Zyberk, co-founders of the New Urbanist movement, an urban planning ideology that stresses walkable, compact cities with a consistent architectural style. Later made (in)famous by the New Urbanist Floridian towns of Seaside and Celebration—the former starring in the The Truman Show (1999) and the latter, originally developed by Walt Disney in the 1990s, sustaining a series of grisly murders—New Urbanism developed a particular association in the Sunshine State with repressed resort towns where the darker truths of American culture fester underneath a cheery veneer.
For all of Duany’s and Plater-Zyberk’s efforts at Windsor, the result is much the same. A meticulously maintained community that offers endless amenities to its guests—a shooting range, art gallery, tennis courts, equestrian trails, croquet, and beach club among them—it appears largely empty during my visit. As a result, Windsor seems to remain suspended somewhere between a false utopia and a luxury ghost town.
A large white picket fence by British artist Michael Craig-Martin stands proud in the lawn between the oaks and the reception, seemingly winking to its context. Candy-colored umbrellas, stilettos, a shovel, and a wheelbarrow make their appearances around the club’s 500-acre expanse as part of Craig-Martin’s solo exhibition at The Gallery, Windsor’s in-house art space. The second installment of a three-year, three-show collaboration with the Royal Academy, it seems the initiative may have helped pique interest in Windsor—membership numbers are reaching an all-time high.
Admission to the Cult of Windsor doesn’t come cheap: golf equity memberships are a cool $200,000, while social membership dues rack up at $14,858 annually—all of which is practically pocket change if you can afford the costs of building your own mansion. Homesites begin at $625,000 and go up to $4,200,000 for waterfront lots.
Although residents are free to choose their own architects they must use Windsor’s builders to ensure total compliance with the Windsor Code: a strict handbook conceived by Duany and Plater-Zyberk that delineates the permitted architectural styles, from building thickness and height to approved pastels and the types of perennials you’re allowed to plant.
New Urbanism spits venom at cars, which its acolytes blame for almost single-handedly ruining cities; Windsor follows suit with modified regulations, permitting the gratuitous use of golf carts (though during my visit, I see more range rovers than residents).
First up on our golf cart tour is the Town Hall. Built in 1999 and designed by the Luxembourgish architect, New Urbanist convert, and devout defender of Nazi architecture, Léon Krier, it’s easily the wackiest building here. A classic PoMo case of proportion mash-up, its large triangular pediment embellished with small geometric cutouts. They run down its long side, where chunky columns are intermixed with fortress-like doors painted eggshell blue. With a dramatic pitched roof that soars high above its vanilla surrounds, the building exudes a mystical aura only brought back to its context by the Mercedes-Benz parked outside.
The doors of the hall are flung open to reveal rows of empty seats; a row of more homely fold-out wooden chairs flanks the entrance, while a giant glitzy obelisk stands proudly at the altar. It’s unclear whether there will be any takers for today’s sermon.
Next up is the Equestrian Centre, where I’m greeted by the forlorn faces of a dozen horses in Windsor’s 26-stable barn. In addition to storage and care for the horses while their seasonal owners are elsewhere, the Centre also offers a 170-yard-long multi-purpose stick and ball field and full-sized polo field for exhibition matches.
Carrying on to the clubhouse, the scent of jasmine wafts up from the eight Stan Smith–designed Har-Tru™ tennis courts. I arrive to see two seniors shake hands at the net and migrate to the patio, Diet Cokes in hand; it’s startling to see real humans actually use the facilities at Windsor, and for a moment this scene breaks the overwhelming impression that Windsor is little more than an elaborate stage set, a pretty piggy bank in which international business moguls can store their cash.
At the Clubhouse’s bar, a bowl of mixed nuts remains out for the ghost nibbler, while the TV blares for no one in particular. The Gallery is upstairs, where Michael Craig-Martin’s graphic 2D works hold their own in a relatively unremarkable space that feels shockingly squished, given the amount of real estate on offer. I head out to the second-floor balcony overlooking the 18-hole golf course—a sumptuous landscape known rather incredibly to members as “Windsor’s Serengeti.” I turn back to face the tinted glass doors of the gallery—Craig-Martin’s sunglass paintings coolly deflecting their context, but still sitting complicit in this parallel universe—and the true insanity of this place comes full circle.
Our final stop is the Beach Club—another Anglo-Caribbean style structure built in 1994, it’s recently undergone a vibrant facelift courtesy of the local designer Rod Mickley. In the new Lodge, a dozen handymen are busy setting up for the night’s fundraising gala.
Returning to the newly remodeled reception, it’s intensely-perfumed interiors prove overwhelming. Stumbling out into the Village Centre designed by Scott Merrill, I fall into its proverbial small town embrace: a Village Store, a real estate office, concierge, post office, gym, and a cafe where residents can catch up over a coffee or pick up fresh produce. Even though it’s totally deserted during my visit (save for one member on a treadmill), this is the closest Windsor gets to feeling like a community.
Outside, the synthetic lawn, shell-infused concrete, and the Exedra—a semicircular amphitheater used for concerts that bears traces of Arcosanti’s bell workshop—bear traces of Windsor’s aspirational New Urbanist roots. Surrounded by a semicircle of spindly palms that rival L.A., it’s here I realize once and for all the movement is best relinquished to this elitist country club.
“New Urbanism has not evolved so much since Windsor, but it has evolved towards Windsor,” Duany has since reflected on the project, as if confirming that the teachings of the movement are more aptly suited for a luxury resort rather than any real city. Crossing its virtually uninhabited expanse, one gets the sense Windsor’s days are numbered, threatened more by rising sea levels than credit defaults. Until then, it remains a peculiar relic of aspirational urban planning, bloated and malformed into a gross excess by all the investment capital stowed away in Florida—because where else would take it?