Is Windsor the Most Un-Florida Place in Florida?

About 90 minutes north of Palm Beach there is a sight that is rare in the state of Florida: an idyllic oasis safe from anything remotely flashy or tacky. There are few cars or cryptocrats, if any. There is only Windsor, a secluded village in Vero Beach cradled by a barrier island along the Atlantic coast.

Some 30 years ago a Canadian couple named Hilary and W. Galen Weston touched down on this spot, where subtropical and tropical climates collide, and acquired 472 acres of land.

"It was still citrus groves and bungalows, dirt roads and wooden walkways, totally unspoiled. We thought we could make it into something very special," Hilary recalls. And they did, developing a residential community that was named after their residence in Windsor Great Park, near London, and informed by the values of the New Urbanism, a planning and development movement that advocates for compact, walkable cities with a coherent architectural style.

A bright Christopher Le Brun painting overlooks a salon in shades of stone, sky blue, and coral, featuring 1970s Spanish rattan chairs, vintage lamps, a Casa Branca Brighton sofa, and a pair of 1950s Maison Jansen white lacquered fauteuils.

Simon Upton

Over the decades Hilary (who was born in Ireland and was once lieutenant governor of Ontario) and Galen (who spent decades steering the family food business, George Weston Limited, one of Canada’s largest conglomerates) commissioned a dream team of architects and designers to build a seaside Xanadu from the ground up. Drawing on design vernaculars from the South Carolina Lowcountry and the British West Indies, where houses feature large porches and courtyards, they fashioned an aesthetic they called Anglo-Caribbean. (Galen died in 2021.)

The tone was set by the casual yet elegant style of Windsor’s Beach Club, which was created by Jaquelin T. Robertson, a patrician Virginian who served as dean of the University of Virginia School of Architecture, and Naomi Leff, who is responsible for the influential interiors of Ralph Lauren’s flagship store on Madison Avenue. As with all good things, however, there comes a time to refresh.

Windsor’s clubhouse, redesigned by Alessandra Branca, features wicker seating by Wicker Works, and Billy Haines side chairs in Casa Branca fabrics.

Simon Upton

Shortly before the pandemic, Hilary invited the Italian designer Alessandra Branca to reimagine the space, which, like most things at Windsor, had been oriented toward the community’s world class polo field, where Galen and his son played with the likes of Prince Charles, and its 18-hole, links-style championship golf course, designed by Robert Trent Jones Jr.

"Windsor had never really been engaged with the beach," Branca says. "Everything was focused on the horses and the golf. That’s where the life was."

The clubhouse’s logia features hand-painted Baroque-style overdoors.

Simon Upton

The designer had the audacious idea to turn things around. Now, after a recently unveiled redesign, the beach plays center stage, boasting a new restaurant and a second dining venue with a veranda overlooking the water.

"For Windsor it was an opportunity to reinvent itself. For me it was a wonderful opportunity to see where Hilary is now," she says. "Hilary has incredibly great taste, which is based in classical architecture, but she loves the flair of new things. She’s game." It was game on.

Branca, who was born in Rome and is based in Chicago, first entered the Windsor scene six ago, when Hilary hired her to redesign the Suites, a collection of accommodations for members’ guests. Branca gave each of the seven units a buoyant, distinctive character, as well as a pergola-like outdoor seating area. Members and guests embraced Branca’s vision, as did the Westons, who asked the designer to update parts of the oceanfront house they had purchased for their guests. Their own home, decorated originally by Hilary in collaboration with the Egyptian-born, London-based designer John Stefanidis, is a study in elegant simplicity.

When Branca returned to revamp the beach club, she took note of Windsor's changing population. During the pandemic an increasing number of the village’s 300 or so residents began spending longer periods there, and she noticed that they were more multigenerational than elsewhere in Florida.

"It’s not Hobe Sound, it’s not Palm Beach," she says. "We looked for ways to accommodate all the different sorts of people there: the young, the old, the kids, the people entertaining, the people having weddings."

Hilary Weston, who founded Windsor, and Alessandra Branca in the clubhouse’s bar in front of a work by Beatriz Milhazes.

Simon Upton

Sizable as the club is (10,000 square feet, with multiple rooms and spaces, indoors and out), Branca felt that it had been underutilized. The earlier layout put a premium on formality at the expense of fellowship, limiting common areas to one group at a time. "I’m Italian,"

Branca says. "From my life in Rome, I know that people like to be where other people are. No one wants to go into an empty room." So she made space for more seating."It’s packed now," she says. "As it existed before, the club wasn’t really embraced by the residents. Now people are embracing it. They hang out there. They have drinks before dinner, drinks after dinner."

The new decor matched the vibe shift, encouraging an environment in which guests feel comfortable in bathing suits or evening wear, in Polo or Ralph Lauren Collection."I mixed in French pieces with some midcentury Italian, midcentury Danish, along with, for example, a Regency game table," Branca says. "There is wicker, brass, and bronze." She also made the bar a little more loungy, installing a plush leather banquette and an ebonized floor and darkening the walls. "I thought we’d make it a little groovier."

Casa Branca Foglia - Leaf

$150 at casabranca.com

In consultation with Hilary, a serious arts patron who has raised millions for the Royal Ontario Museum, Branca also brightened up the club with a collection of contemporary works by artists including Damien Hirst, Beatriz Milhazes, and Christopher Le Brun; there’seven a 2021 video installation in the lounge by the American multimediaartist Allison Janae Hamilton, whose work often examines the natural environment. "It was a real collaboration," Branca says of working with Hilary.

One other piece nods to the history and whimsy of South Florida: an annotated color sketch for Christo and Jeanne-Claude’s Surrounded Islands, a 1980–3 environmental work that saw them outline islets in Miami’s Biscayne Bay with pink fabric. Needless to say, Branca herself is not afraid of color. She worked primarily with stone, sky blue, coral, and white, but she threw a curveball every now and then. "It’s all muted, with a little pop," she says. "Because if you don’t want a pop, you can't call me."

Lead image features Casa Branca–upholstered beach chairs before an Atlantic sunrise.

This story appears in the February 2023 issue of Town & Country. SUBSCRIBE NOW

James Reginato

A journalist and writer-at-large for Vanity Fair, Reginato is the author of Growing Up Getty