The Plutocrats’ Playground: inside Hilary and Galen Weston’s exclusive enclave of palatial vacation homes

The Plutocrats’ Playground: inside Hilary and Galen Weston’s exclusive enclave of palatial vacation homes

Hilary and Galen Weston built an unimaginably luxe development of multimillion-dollar vacation homes in Florida. With royals, CEOs and socialites, they play polo, hit the links, plan corporate takeovers and party. An inside tour of Toronto-by-the-sea

The Plutocrats’ Playground: inside Hilary and Halen Weston’s exclusive enclave of multimillion-dollar vacation homes
Windsor was designed as a trendy New Urbanist community (Image: Durston Saylor)

Vero Beach, a sprawling city on Florida’s Atlantic coast, has long been a popular winter destination for Toronto snowbirds. It’s a town of cookie-cutter shopping plazas (Starbucks, Target, Bed Bath and Beyond; Starbucks, Target, Bed Bath and Beyond), mid-market chain hotels and endless gated communities built to serve the thousands of seasonal residents who converge in their comfortable senescence to play golf and bridge with like-minded retirees. For years, Vero Beach was stuck with the pejorative nickname Zero Beach, affirming its reputation as a sleepy haven for the Probus set.

However, at the northern end of a barrier island off the coast of Vero sits one of the most exclusive and unusual residential developments in Florida: Windsor. There’s no roadside gatehouse, only the uninterrupted view down a beautiful driveway—two rows of dark-grey oaks line the long avenue, forming a natural archway overhead. To the left is the polo field; to the right, the equestrian centre, its perfectly geometric stable and paddocks floating above the perfectly manicured, perfectly green lawn.

This is how one arrives at Windsor—and finds oneself adopting the formal pronoun “one.” It’s hard not to get swept up in the beauty of the place. This is Vero Beach as conceived by Galen and Hilary Weston, Canada’s first family of taste. They’ve transformed 168 hectares of former citrus groves into an enclave of 226 houses. The remaining lots range from $300,000 to $3.1  million; built homes sell for as much $15 million. Even the streets have Westonian names: Wittington (one of the family holding companies), Frayne (Hilary’s maiden name), Renfrew (their department store) and Belvedere (the former Windsor Great Park residence of Edward VIII, now a Weston country home). And in keeping with the Westons’ devotion to perfection, not a leaf or blade of grass is ever out of place.

In the echelons of wealthy Torontonians, Galen and Hilary Weston are on a ladder all their own. In addition to the Loblaws supermarket chain (and now Shoppers Drug Mart), the Westons own the luxury department stores Holt Renfrew, Selfridges, Brown Thomas (in Ireland) and de Bijenkorf (in the Netherlands). Forbes magazine pegs their net worth at $8 billion. They divide their time between homes in Forest Hill, England, Florida and, in the summers, a remote island in Georgian Bay. They’re friends with the Queen and Prince Philip, Prince Charles and Camilla, and dozens of other aristocrats and titans worldwide. They’re sometimes referred to as Canada’s royal family.

Windsor, thanks to the Weston’s connections, has become a gathering place for an international community of jet-setting plutocrats who aren’t defined so much by nationality or political persuasion as corporate allegiances. They are a nation unto themselves: a collection of highly successful individuals brought together by their love of business, travel, philanthropy, culture and, increasingly, the exchange of high-minded ideas.

It is a testament to the Westons’ foresight that, 24 years ago, well before today’s plutocrats were an identifiable group, they envisioned a not-quite-retirement community built in their image, where their peers from the U.K., Europe, Canada, the U.S. and beyond could convene for several weeks a year to both work and play (to the modern plutocrat, work has come to resemble play, and vice versa).

A who’s who of the Toronto business elite has followed the Westons to Windsor. One of them jokingly refers to it as “the Bubble”—by which she means a welcome escape from her daily concerns back home. But the name also captures the shiny exclusivity of this immaculate place—a playground of happy rich people cocooned from the rest of the world.

Last March, I flew down for a personal tour of Windsor. Hilary Weston, impeccably dressed in a white tailored jacket and pants, greeted me inside her Windsor compound, a collection of rectangular, balconied buildings overlooking a vast neoclassical courtyard with a fountain and swimming pool. She invited me up the split staircase at the east end of the courtyard, which leads to the Westons’ private living quarters overlooking the Atlantic. Well-preserved at 71, she speaks in the neutral tones common to British aristocrats. Over a cup of tea, she explained the history of Windsor with the subdued monarchic pride of a queen content with her domain. (This is particularly acute when she speaks of visiting “the village houses,” the vaguely feudalistic term for the homes at the centre of the Windsor development.)

The Plutocrats’ Playground: inside Hilary and Halen Weston’s exclusive enclave of multimillion-dollar vacation homes
The clubhouse at Windsor’s golf course (Image: Durston Saylor)

The Westons didn’t initially plan to get into the real estate game. After years of vacationing in the Bahamas—at Lyford Quay when their children, Alannah and Galen Jr., were young, and later at Windermere Island in Eleuthera—they decided they wanted a place that offered more than beaches and bicycles for their teenage kids. They chose Florida, because of its easy access, proximity to top-notch medical facilities and varied recreational options. They set out in search of a relatively unspoiled tract where they could build ranches and ride horses on the sand. When they visited Vero Beach, they were struck by the surrounding rural land. Outside the city lie acres and acres of cattle farms and citrus groves.

The plan was to buy up some property on which they and about six other families—members of Galen’s extended clan and some close English friends—could keep horses. The year they visited, Florida was hit by a freak ice storm, and the citrus growers around Vero Beach lost their crops. The following year, dozens of farms came on the market, and the Westons bought 180 hectares’ worth of grapefruit groves. Galen didn’t see the point of developing so much land for personal use. If they were going to all that trouble, better to make a business out of it. They settled on the concept of a village by the sea.

The Westons, no fans of the Spanish colonial style that dominates Florida architecture, opted to hire Andrés Duany and Elizabeth Plater-Zyberk, the Miami husband and wife team behind Seaside, the famous New Urbanist community in the Florida Panhandle (and the less famous Cornell in Markham). At the time, the radically old-fashioned New Urbanist principles of an integrated, walkable community were trendy in urban planning; Prince Charles had adopted them in commissioning the Léon Krier–designed town of Poundbury in Dorset.

Together the Westons and their architects designed a plan of 150 houses clumped together instead of dotted around a golf course, as they are in most Florida developments. The architectural style was inspired by the plantation homes in Savannah and Charleston. At Windsor, each home would have a guest wing, modelled after the old carriage houses of the South.

The Westons gambled that people didn’t necessarily want to live high on the hill, as Hilary put it, but close together in a town with a general store, post office, real estate office, inn, town hall and gym. They imposed a strict architectural code, dictating setbacks, roof lines, even a colour palette for house exteriors. Hilary says this was to create a cohesive look while also protecting the owners—lest some yahoo buy the lot next door and build a faux Taj Mahal. According to the rules, you can build something nearly as big as the Taj Mahal, but it can’t look like a mansion; instead, families build compounds comprised of separate buildings in different hues, with distinct roofs of varying materials—tin, shake, slate—and heights. Houses are set close to the road to allow room for private interior courtyards—the main living area for many families.

The result is a village centre that is serene but oddly impersonal. Windsor can seem eerily deserted, like an abandoned architectural theme park. The effect is magnified when the development is underpopulated, as it was during my visit the week before March break. I felt a little silly stopping my golf cart—Windsorites’ preferred mode of transportation—at village intersections when there wasn’t another soul or vehicle in sight.

Halfway through the first phase of the development, Hilary was named lieutenant-governor of Ontario and temporarily stepped away from her passion project. Her daughter, Alannah, took over as creative director—a position she now holds at Selfridges in London—and launched what would become a world-class art gallery on the property. The Westons then built a links-style golf course designed by Robert Trent Jones Jr., one of the most celebrated golf course architects in America; a main clubhouse with a Yabu Pushelberg interior; and eight tennis courts, each separated by hedgerows of scented jasmine. The courts were designed by the American tennis legend Stan Smith, perhaps better known for his eponymous line of Adidas tennis shoes. Windsor also has a beachside clubhouse with a 25-metre infinity pool and private cabanas.

The first visitors to Windsor were wealthy European friends of the Westons—James and Julia Ogilvy, the son and daughter-in-law of the Queen’s cousin Princess Alexandra; the Polish prince Count Vincent and Lady Victoria Poklewski-Koziell; and Hubert and Isabelle d’Ornano, the Parisian owners of the luxury skincare line Sisley—and Americans from the northeast, people who summered in Martha’s Vineyard or Nantucket and immediately understood the village concept. Other long-time members include the Swarovski family, Amway heir Dick DeVos and Ivan Lendl, the former tennis star and current coach of Wimbledon champion Andy Murray.

The Plutocrats’ Playground: inside Hilary and Halen Weston’s exclusive enclave of multimillion-dollar vacation homes
The Westons’ Windsor house has a view of the Atlantic (Image: Durston Saylor)

In the early ’90s, the market turned, and the Westons found themselves floating an ambitious project through a decade-long dry spell. In 1991, the neighbouring Orchid Island development—a more traditional Floridian resort community with an Arnold Palmer–designed golf course and an $8-million beach club—went into receivership, becoming one of those surreal luxury ghost towns particular to the Florida landscape. Galen purchased the 240-hectare property in 1994 for $20 million and, over the next 10 years, successfully built out the 376-home community. The proceeds helped support the struggling Windsor.

One of the first Canadian couples to buy in Windsor was Phil and Jane Giffin, wealthy Montrealers (he’s originally from Toronto; she’s a granddaughter of the Montreal financier J. W. McConnell). They built a château-style home in 1993, in what is now the heart of the Windsor village, and waited out the long sales drought surrounded by virtually no one.

Many in the Westons’ Canadian circle shared preconceived notions about Florida—of grey-haired retirees holed up in gated communities, or beaches crammed with oiled-up sun-worshippers in scanty bathing suits. “I think Canadians thought we were mad,” Hilary says. Valerie Pringle, the cheery former journalist and TV host, was one of the skeptics. She and her husband, Andy, a former managing director of RBC Capital Markets and now chair of the Shaw Festival and the capital campaign for Fort York, had never even been on a beach holiday. In 1995, they were invited down to Windsor by their friend Jennifer Bell, the daughter of a former CEO of Abitibi, and her husband, Bay Streeter Michael Wills. The Pringles’ visit coincided with the official opening of the Windsor beach club, and there were lots of festivities attended by fancy people. “We kept thinking, ‘We don’t really belong here, it’s such an elegant place—but man, is it ever nice,’ ” Valerie says.

On the second day of their visit, Valerie was called back to CTV early to interview Lucien Bouchard, who’d just returned to the House of Commons after having his leg amputated. When Andy flew back to Toronto the following day, he announced he’d bought a four-bedroom house next door to the Willses’.

Today, roughly one out of five Windsor members is Canadian, and you can trace their march into Windsor like a society family tree: the Giffins brought the Willses, the Willses brought the Pringles, who in turn introduced their Toronto neighbours, the pixie-like dynamo Margot Franssen and her husband, Hall  Tingley (Quig to his friends). The couple had built the Body Shop brand in Canada before selling it back to its parent company in 2004 for $26 million. Franssen spends six months of the year in Windsor, flying back and forth to New York and Toronto for various board meetings, and drives around in a golf cart with the words “So Happy” painted on the side.

Franssen tells a story about having her sister and brother-in-law down to visit, and her brother-in-law standing on her balcony, which overlooks the first tee of the golf course. He couldn’t believe how meticulously maintained the property was. As he spoke, a palm leaf fell from an overhanging tree and landed on the manicured lawn below. Just then, a maintenance worker pulled up, picked up the leaf and threw it in the back of his truck. It was the type of chance occurrence that can only happen in a place that, during peak season, has a staff-to-member ratio of one to three.

There are further small-world connections: Andy Pringle gave fellow Windsorite and Canadian banking titan Gord Nixon his first job in the bond department at RBC; Nixon grew up summering in the Eastern Townships with Michael and David Shaw, the sons of Sir Neil Shaw (ex-chairman of the sugar behemoth Tate and Lyle in England). All three Shaws own places in Windsor; Valerie Pringle went to kindergarten with David’s wife, Martha.

During my Windsor visit, I met up with Rob Prichard, the voluble chair of everything-in-Toronto and his quiet, even-tempered wife, Ann, a former government lawyer turned painter. Their house is located right across from the general store on the corner of Wittington Avenue and Belvedere—an appropriate intersection given Prichard’s close ties to the Weston family. He is a long-time board member of George Weston Limited and a golfing buddy of Galen’s. The two were among the six Canadians who attended this year’s exclusive Bilderberg Conference in Hertfordshire, England.

The Plutocrats’ Playground: inside Hilary and Halen Weston’s exclusive enclave of multimillion-dollar vacation homes
The development’s beach clubhouse has a 25-metre infinity pool (Image: Durston Saylor)

Prichard invited me for a round. As we headed to the club in his golf cart, he announced he wanted to stop by the Pringles’ to see someone who was staying there for the week. He popped inside the house and yelled hello, emerging moments later with Peter Oliver, co-owner of the Oliver and Bonacini restaurant empire. Oliver and his son-in-law joined us for nine holes.

In an effort to boost interest in the development, the Westons began offering free weekend visits to prospective Canadian buyers. Jan Gould and her husband, Jay, president of New York Fries and South St. Burger, went down for a long weekend in 1999, along with their two young sons. On the second day, they sent their kids off for riding lessons at the equestrian centre so they could play a round of golf. As they stood outside the clubhouse, about to tee off—there are no tee times at Windsor, which has a walk-on policy for members—they heard their sons calling their names. There they were, waving from atop their horses, faces beaming. “It was right out of a commercial,” Jay says. “Like someone yelled, ‘Cue the horses!’ and along they came.” By the end of the weekend, the Goulds had bought a lot in the village.

Over the years, Windsor’s exclusivity has drawn a number of high-powered political types looking for holiday time away from the media hordes. Jean Chrétien’s daughter, France, and her husband, André Desmarais, co-CEO of the Montreal-based, multibillion-dollar Power Corp., owned a vacation home in Windsor. For a week every year throughout the ’90s, the place became 24 Sussex Drive South, as Chrétien and his wife, Aline, flew down for a mid-winter getaway. American congresswoman Nancy Pelosi has a friend with a house in Windsor village, which she visits from time to time. On such occasions, Windsor is overrun with secret service agents.

In 1991, the Westons built a new oceanfront home for themselves next to the beach club, where they lived for about seven years. One evening, Pete Peterson, the billionaire private equity financier who was once secretary of commerce under Richard Nixon, stopped in while Galen was entertaining some new residents. Peterson said he’d looked around the property, and the only house he was interested in was theirs. Seeing that Galen was taken aback, Peterson said, “Well, your business card says ‘real estate’ on it, doesn’t it?” He made Galen a generous offer and gave him 24 hours to decide. Galen and Hilary sold the house, furniture included, and built a bigger and better one next door.

Windsor is part country club, part corporate retreat—like one big networking campus for the global elite. Hilary tells me about a group of gun enthusiasts who met at the Windsor Gun Club (run by the former Olympian Nikolaus Szápáry) and now go on annual shooting trips together; last year they went to Highclere Castle, otherwise known as Downton Abbey. Others go on wine tasting excursions abroad. Torontonians have befriended Windsorites from Ohio and Massachusetts, but they’ve also cross-pollinated in ways Hilary never imagined.

One Christmas at Windsor, her son, Galen Jr., was introduced to Alexandra Schmidt, the daughter of Windsorites Peter and Christine Schmidt and an heiress to the Bata shoe empire. The Schmidts lived a few doors down from the Westons in Toronto, but their kids had never met. Five years later, the two were married in the Schmidt family’s Provence château. Meanwhile, the Westons’ nephew Geordie Dalglish (his mother, Camilla, is one of Galen’s sisters) met his wife, Swith Bell, at Windsor. And Swith’s sister, Cecily Wills, got engaged to James Eaton, of the department store clan, at Windsor in 2008. They were married before 130 guests in a lavish Windsor wedding (ceremony in the town hall; reception at the beach club) soon after.

My first night visiting Windsor, the Westons hosted the opening reception for an Aspen Institute symposium on ocean conservation. It was a semi-formal affair, with cocktails on the main floor of the beach club overlooking the pool and a sit-down dinner upstairs. I met some couples from Chicago, who coincidentally all lived on the same street in the upscale suburb of Winnetka but didn’t know each other until they came to Windsor. When I told them I was writing a story about the place, one of them nodded in Hilary’s direction and asked playfully, “Have you met the queen yet?”

If high-end real estate is a rising global currency for the super-rich, then exclusive cultural events are a way for luxury developments to distinguish themselves. From Miami to Argentina to Abu Dhabi to Hong Kong, developers are building residential properties that include concert halls, art galleries and even on-site studios where visiting international artists can live and work. The types of social events that once filled the calendars of the wealthy elite—debutante balls, society fundraisers, regattas—have been usurped by more high-minded get-togethers like the World Economic Forum in Davos, the Bilderberg Group conferences, TED and the Aspen Ideas Festival. Not all Windsorites are plutocrats, of course, but they are a socially engaged bunch who spend their leisure time trying to improve themselves and the world. Like the environmentally conscious Westons, they’re especially interested in conservation projects.

The Plutocrats’ Playground: inside Hilary and Halen Weston’s exclusive enclave of multimillion-dollar vacation homes
The celebrated golf course architect Robert Trent Jones Jr. designed Windsor’s links (Image: courtesy Matt Lowden)

The Aspen symposium is one of many events held at Windsor over the last several years. There’s a Windsor Salon Series (past guests include Peggy Noonan, Niall Ferguson, Christopher  Hitchens and Jeff Speck, co-author of Suburban Nation, who called Windsor “the most beautiful modern place in the world.”) There are impromptu talks organized by Windsor members through their personal connections—a couple of weeks before my visit, the governor of Florida, Rick Scott, attended a dinner; another week, a recently retired Navy Seal told stories of fighting terrorists in Iraq and Afghanistan.

Hilary is passionate about Windsor’s art gallery, which recently joined forces with the illustrious Whitechapel Gallery in London. She and Whitechapel’s director, Iwona Blazwick, put on shows at Windsor to coincide with Art Basel Miami Beach. The most recent one was an exhibition of work by the Transylvanian twins Gert and Uwe Tobias. This year, the gallery will display lithographs and etchings by Jasper Johns. The point isn’t to sell art, but to draw visitors (the gallery is open to the public by appointment) and to build the profile of the Windsor brand.

The Aspen symposium at Windsor was the brainchild of Leonard Lauder, the octogenarian chairman emeritus of Estée Lauder and a trustee of the Aspen Institute. He called up his good friends the Westons in 2012 and asked if they’d be interested in collaborating. A year later, they’d sold 111 tickets to Windsor club members and a collection of local and international conservationists.

Before dinner, Galen stood up to greet the assembled guests and, after surveying the packed dining room, joked to his wife, “Well, Hils, looks like we may need to build a bigger beach club.” He then introduced some of the symposium participants, including Queen Noor of Jordan, who was staying with the Westons; Caroline Hermans, head of environmental stewardship at the Clinton Global Initiative; and David de Rothschild, a self-described adventurer and member of the European banking family. The keynote speaker for the evening was M. Sanjayan, the lead scientist at the Nature Conservancy and a science and environment contributor at CBS. We then ate a four-course meal, while Sanjayan delivered a rather grim speech about the state of the oceans (“the death of the oceans has been foretold”) in a ­surprisingly upbeat manner. (His closer: “The question for us is not are we going to sink or swim, but how are we going to swim together.”)

The following morning, guests gathered at the golf clubhouse for breakfast (dress: resort casual, collared shirts required for men) before heading over to Windsor’s town hall for panel discussions. Once everyone was seated inside, Galen and Hilary made their colour-coordinated entrance—she in a pink Chanel suit; he in a blue-and-white-striped collared shirt, a pink cashmere sweater slung over his shoulders. Then we all settled in for three hours of discourse on ocean conservation, including the success of a man-made reef in the Gulf of Mexico that resuscitated a marine eco­system devastated by the BP oil disaster. It was the sort of loftily ambitious discussion that can only be broached by people with the lofty ambitions afforded by money and connections. It’s a seductive formula. A couple of times I caught myself nodding along approvingly—Yes! We can do this!—before coming back down to earth.

At noon, guests hopped into chauffeur-driven golf carts and returned to the beach club for a sustainable seafood lunch of royal red shrimp with locally farmed greens and pan-seared mangrove snapper, while a peppy young entrepreneur named Kristofor Lofgren, owner of the Oregon restaurant Bamboo Sushi, delivered a closing speech. The highly palatable message? Conservation and commerce aren’t mutually exclusive.

After lunch, I bumped into Galen Weston in the parking lot of the beach club. He was pleased with how the symposium had gone and how much he’d learned. He had been expecting the discussions to be much more scientific and complex, and was relieved to find them both accessible and inspiring. “It wasn’t all doom and gloom,” he said. “It’s amazing how much is being done.”

As the guests dispersed, I borrowed a Windsor golf cart for a final solo tour around the property. All was quiet and sedate, the residents having retreated behind their gates to enjoy their private oases. I tried to imagine what it would be like to be a Windsorite—to walk the white crushed-shell pathways, comfortably oblivious to their glow. Finally, I followed a handsome boardwalk down to the deserted beach and watched the massive waves gobble up the shoreline—a minor bit of turbulence on an otherwise flawless blue horizon.