Communities
The barrier island, club by club
Barrier island communities, from John's Island to Central Beach, each with a guide and live inventory.
All communitiesBarrier island communities, from John's Island to Central Beach, each with a guide and live inventory.
All communities
A village by the sea, built on 472 acres of former citrus groves by the Weston family and planned by the architects who coined the term New Urbanism. Fewer than 400 homes, a polo field at the center of it, and the Atlantic at the end of the street.
Windsor does not look or function like the rest of Florida's club communities, and that is deliberate. W. Galen and Hilary M. Weston founded it in 1989 on an old citrus plantation and hired Andrés Duany and Elizabeth Plater-Zyberk — the planners who gave New Urbanism its name — to lay it out as an actual village rather than a subdivision with a gate.
The result is a walkable town plan with a real center. Houses sit close to the street behind walls and courtyards, built to an Anglo-Caribbean design code that keeps the whole community visually coherent without making it repetitive. The Village Centre, designed by architect Scott Merrill, is reached through an allée of live oaks at the convergence of five roads, and it holds the Village Store, the Exedra amphitheater, the greens, the concierge office and the post office. Residents walk or bike to breakfast. Dogs are part of the culture.
For buyers, the practical consequence is that Windsor trades on architecture and town planning as much as on square footage. Homes here are frequently published, and the design review process is real — something worth understanding before you plan a renovation.
Windsor began as a place for the sporting life among family and friends, and the amenity list still reflects that more than it reflects a conventional country club.
Robert Trent Jones Jr.
An 18-hole links-style course routed through the community, with a clubhouse and patio dining overlooking the fairways.
Full-size field, 26 stables
A full-size polo field for exhibition matches, a 170-yard multipurpose field for training, stables and a training ring. The biennial Windsor Charity Polo Cup is the community's signature event.
Stan Smith
A tennis centre laid out by the Wimbledon champion, with its own competitive and social calendar.
Championship greensward
A croquet lawn built to championship standards overlooking the polo field, all-white attire observed, with Wine & Wickets gatherings a member favorite. The offsite Gun Club runs European clay shooting games.
10+ miles
More than ten miles of hammock-shaded trails for riding, biking and running, with a new Fitness & Wellness Centre planned.
Jaquelin Robertson, architect
An Anglo-Caribbean oceanfront clubhouse with a 25-meter pool, poolside grille, open-air bar and a second-floor dining room under soaring rafters with sea views. The Salon & Bar was reimagined in 2022 by designer Alessandra Branca with Hilary Weston.
Dining runs from the oceanfront Beach Club dining room and its coastal Italian menu, to the Clubhouse patio over the fairways, to the Village Store — the community's morning hub for coffee, breakfast and light lunches, plus groceries, newspapers and wine.
The Windsor Wine Cellar, developed with consulting firm WineTrend, holds more than 40,000 bottles in climate-controlled storage alongside an elegant tasting room. The Windsor Wine Association has over 100 members who gather through the season.
Culture is not an afterthought here. The Gallery at Windsor, opened in 2020, has exhibited work from the Weston Collection including Christo and Jeanne-Claude, and it now anchors a season of museum-caliber exhibitions, performances and lectures. Town Hall doubles as the community chapel.
The Windsor Suites, overlooking the polo field in the Village Centre, house members' guests — a genuinely useful amenity for owners who entertain visiting family.
Windsor's low density — more than 350 homes spread over 472 acres — means very few properties are available at any one time, and the segments behave differently from one another. What you are choosing between:
I listed and marketed a $16 million Windsor oceanfront estate — 13 bedrooms, four guest cottages, 1.7 acres — and took it to a national audience, generating coverage in Robb Report, Mansion Global and Realtor.com among others. That is the level of exposure a Windsor property deserves and rarely gets.
Michael Merrill, Partner, The Exclusive Group at Douglas Elliman
Windsor is a private sporting club as well as a residential community, and membership questions — categories, dues, current terms — are handled directly by the Club at (772) 388-8400 or through windsorflorida.com. Terms change, so treat anything you read secondhand as a starting point only.
One thing worth knowing going in: Windsor's developer operates its own in-house brokerage, and much of what you will see marketed comes through that channel. Having independent representation on your side of the table matters here more than in most communities — for pricing perspective, for comparables from outside the community, and for a candid read on how a Windsor home will resell.
If you are weighing Windsor against its neighbors, I cover those too: John's Island, Orchid Island, Indian River Shores, The Moorings, Riomar and Central Beach.
Windsor sits on the barrier island between the Atlantic and the Indian River Lagoon, about 15 minutes north of Vero Beach's Ocean Drive shopping and dining district along A1A. Melbourne Orlando International is roughly 45 minutes north; Orlando International about 90 minutes northwest; Palm Beach International about 90 minutes south. Vero Beach Regional Airport handles private aviation about 20 minutes away.
Windsor
3125 Windsor Boulevard, Vero Beach, FL 32963
(772) 388-8400
Private community — access for members, residents, and guests with appointments.
Windsor is the thinnest market on the barrier island. Fewer than 400 homes exist, most owners hold for decades, and a large share of what does trade is marketed through the developer's in-house brokerage rather than the MLS. The public MLS record for 2025 through mid-September 2026 shows a single closed sale, which tells you more about how Windsor sells than about demand.
That is exactly why independent representation and early notice matter here. I track Windsor ownership and off-market activity directly, and I have listed and marketed the community's $16 million oceanfront estate to a national audience. If you want a real read on values, ask me for current comparables rather than relying on a published average built on one or two sales.
3125 Windsor Boulevard, Vero Beach, Florida 32963 — on the barrier island between the Atlantic Ocean and the Indian River Lagoon, roughly 15 minutes north of Ocean Drive. The community covers 472 acres.
W. Galen and Hilary M. Weston of Toronto established Windsor in 1989 on former citrus land. Andrés Duany and Elizabeth Plater-Zyberk created the New Urbanism master plan and the Anglo-Caribbean design code; architect Scott Merrill designed the Village Centre.
Golf by Robert Trent Jones Jr., tennis by Stan Smith, an Equestrian Centre with a full-size polo field, a championship croquet greensward, a gun club, more than ten miles of shaded trails, an oceanfront Beach Club with a 25-meter pool, a 40,000-bottle wine cellar, and The Gallery at Windsor.
More than 350 across 472 acres — unusually low density for a Florida club community. Product ranges from Windsor Park condominium residences through village courtyard homes, fairway-front houses and oceanfront estates, with the North Village still building out.
Windsor's final development phase, on the last undeveloped land near the Indian River Lagoon. It follows the same New Urbanism principles with a stronger sustainability focus and adds residences, civic green space and new amenities. New construction there is sold through the developer.
No. The community is gated and the club is private. Golf, the Beach Club, the Equestrian Centre and the dining venues are for members and their guests.
