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.)