The Westons, Windsor and the Plutocrats.

W. Galen Weston O.C., C.V.O., OOnt., B.A., LL.D, DDIV passed away peacefully at home on April 12, 2021, at the age of 80, after a long illness faced with courage and dignity.

“We had been looking for a place to establish a winter home to escape the brutal Canadian winters and play polo,” says Hilary Weston, who founded Windsor in 1989, in Vero Beach, Florida with her husband Galen.

The land that so captivated them was a former citrus plantation in an idyllic location between the Indian River and the Atlantic Ocean.

Initially, the Weston’s built a few homes for friends and family and a polo field where Mr. Weston – an accomplished polo player – enjoyed hosting spirited matches. The polo field was soon followed by a championship golf course, and before long, inspired by the joy they found in this beautiful setting, they began to pursue a truly expansive vision – a community with small-town charm, world-class sporting amenities and sophisticated cultural events.

When it opened in 1989 primarily as a polo club, Windsor indulged in some excess: Prince Charles visited annually to play his favorite sport. Those royal ties caused the Weston’s to name the community after the location of their beloved English home in Windsor Great Park.

At first, the billionaire couple, whose business holdings include Selfridges and Brown Thomas department stores in the U.K. and Ireland, only wanted to build a compound for family and friends

But over time, the Weston’s transformed 168 hectares of former citrus groves into an enclave of 226 houses.

Yet in the 32 years since their resort began, many of its then-radical features have become the new normal. The vision soon led to a larger multigenerational resort that combined their passions: sports—particularly polo, tennis and golf—beach living, arts and environmental awareness. 

But it was not developed without sophisticated regional planning.  Windsor pioneered modern urban planning. For them, the key to creating a community that represented their passions even while maintaining a relaxed lifestyle was the nascent New Urbanism movement.

A response to 20th century urban sprawl and car dependency, New Urbanism first arose in the 1980s with the town of Seaside, Fla., recognizable for its Rockwellesque aesthetic and pedestrian-focused grid.

Because renowned urban designers Andrés Duany and his wife Elizabeth Plater-Zyberk, principals of Miami-based firm DPZ, planned Seaside, the Weston’s tapped them to work on Windsor. Rather than concentrating the community around a golf course, as was the trend of other resorts at the time, the Weston’s wanted a strict planning code that would allow them to create a village center and provide an architectural character inspired by America’s earliest cities such as Charleston and Savannah, as well as the British West Indies. Today Windsor calls this design “Anglo-Caribbean.”

“The Weston’s actually took a tremendous risk,” says Duany, who cofounded the Congress for the New Urbanism in 1993. “There are so many of these communities now—this is a normative way of designing new resorts. But at the time it was pioneering.”

At first glance, the picture-perfect village, featuring 350 unembellished homes on densely organized lots, eco-friendly design and landscaping, walking trails through native hammocks, and a placid town center with an amphitheater and a general store, seems freshly built. Yet in the 32 years since this resort began, many of its then-radical features have become the new normal.

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. 

Prior to Mr. Weston’s death, he and his wife divided 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, now deceased, 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.

Windsor Clubhouse, Vero Beach, Florida

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