We begin the 2025-26 season on a sad note. This past August, our beloved co-founder. The Hon. Hilary M. Weston passed away. For more than 35 years, Mrs. Weston has been involved in every aspect of Windsor’s evolution. For her, this community—which she and Mr. Weston affectionately called “their village by the sea”—truly was a passion project. Her presence at Windsor will be dearly missed.
Mrs. Weston was heavily involved in the design of the North Village and would be pleased with the progress being made on Windsor’s final neighborhood. We have excavated a lake and estuary, and begun construction on a boardwalk that spans the lake and sweeps around a new rookery island. Main entry roads are paved, the new ellipse-shaped park is taking shape, and we have broken ground on the neighborhood’s 13,800-square-foot Fitness & Wellness Centre.
In this issue, we introduce a new column sharing updates on the Vero Beach community. With planned expansions for both the Vero Beach Museum of Art and Riverside Theatre, national recognition of McKee Botanical Gardens, and new direct flights into the Vero Beach Regional Airport, it is an exciting time for the area. See page 6 for guest columnist Irina Woelfle’s update.
As always, we welcome new visitors to experience the vibrant lifestyle at Windsor and learn more about our real estate offerings. Please contact me or any of our Sales team members listed below to schedule a visit.
Enjoy our first newsletter of the season. Best wishes for the upcoming holidays.
Sincerely,
10085 St. Augustine Avenue
5 BEDROOMS | 6 FULL, 2 HALF BATHS | $12,500,000
Panoramic golf course views, a lakefront pool terrace, and a spacious central courtyard with a reflecting pool set a tone of elegance and ease in this five-bedroom home in the heart of Windsor’s South Village. Meticulously finished with several recent renovations, this impressive home exemplifies timeless luxury. Extensive custom details elevate the aesthetics while enhancing comfort inside and out. Highlights include a dedicated bar and lounge with wine storage, designer wall coverings, walnut flooring with inlaid honed travertine borders and handcrafted millwork with concealed storage. With expansive indoor and outdoor spaces for relaxing, dining and entertaining, this residence is an ideal retreat any time of year.
The Hon. Hilary M. Weston was known in many circles for her business acumen, keen sense of style, and remarkable generosity.
At Windsor, the Members express deep appreciation and gratitude not only for her pivotal role in co-founding and stewarding the community, but also for graciously offering her warm hand of friendship throughout the years.
Mrs. Weston died peacefully at her home in England surrounded by family on August 2.
Hilary Mary Frayne was born in Dublin, Ireland, on January 12, 1942. At just 16, she worked as a fashion model to help support her family. A few years later, she was to meet her future husband, Canadian Galen Weston. They were married in the U.K. in 1966 and the couple raised two children, Alannah and Galen.
The Westons moved to Toronto in 1972 to revive the family’s Loblaw supermarkets. Through the years, Mrs. Weston would be key to the success of their businesses in Canada and Europe, serving as deputy chair of Holt Renfrew, a director of Brown Thomas & Co. in Ireland, and a director of Selfridges Group based in the U.K.
In 1997, Mrs. Weston became the 26th lieutenant governor of Ontario, championing the achievements of volunteers, youth and women. She was the recipient of numerous honorary degrees and awarded the Order of Canada and the Order of Ontario for her public service and philanthropy. Her dedication to social issues and philanthropy continued throughout her life.
Mrs. Weston’s many talents and skills also were showcased when the couple bought land on a barrier island in Florida in the early 1990s.
Seeking a warm weather family escape, the couple began to transform the acreage into an exceptional New Urbanist community known as Windsor. Under Mrs. Weston’s watchful eye, the forward-thinking seaside village would exceed its aspirations by creating award-winning architecture, world-class sporting amenities, outstanding cultural arts programming, and, most of all, a sense of place.
Mrs. Weston will be remembered as both a woman of great distinction and a person deeply committed to the happiness and well-being of others. She will be dearly missed by all at Windsor and throughout the local Vero Beach community.
Portrait of The Hon. Hilary M. Weston by Chris Nicholls
10701 Charleston Drive
6 BEDROOMS | 6 FULL, 1 HALF BATHS | $5,950,000
Set on a premier corner property along the golf course in Windsor’s Village, this well-conceived residence, originally built in 1995, boasts more than 7,000 square feet. Its welcoming entry loggia leads to a central courtyard with a large swimming pool. Expansive living, dining, and entertainment areas, along with the bedrooms, capture sweeping western views of Windsor’s iconic links-style golf course. Designed for effortless indoor-outdoor living, all ground-floor spaces and most second-floor spaces open onto deep loggias or porches.
10420 Eton Way
One of the few remaining opportunities to build on Windsor’s oceanfront. From the Village of Windsor, a private tunnel leads to Windsor’s Beach Club and oceanfront neighborhood. Lush native landscaping along Eton Way creates additional privacy from the street and adds to the neighborhood’s “Old Florida” feel. Building placement standards for homes on the ocean are attentive to protecting Windsor’s native dune vegetation and marine life, while still allowing for the most spectacular ocean views and private beach access from each home.
This expansive five-bedroom residence located on the second floor of Windsor Park Residences features three exposures with sunset views sweeping across the lush conservation area. Custom cabinetry and Calacatta Gold marble countertops bring sophisticated touches to the kitchen and bathrooms. Elegantly crafted interiors are finished with refined details including decorative millwork, custom cabinetry, and 7″ -wide oak flooring throughout all living areas. Covered porches off the great room, primary bedroom, and two of the guest suites allow for seamless indoor-outdoor living.
Art, Stage, and Gardens
VERO BEACH’S CULTURAL TRIO
Vero Beach is undergoing a transformation that would be remarkable anywhere yet feels like a natural evolution of the already exceptional seaside community.
What has long served as the town’s cultural backbone—Vero’s distinguished museum, Broadway-caliber theater, and historically significant botanical garden—is being reimagined with bold new vision and, in the case of the museum and theatre, well over $100 million in capital investment.
These concurrent developments are reshaping Vero Beach’s identity with a sophistication that places it in conversation with the nation’s most cultivated seasonal enclaves. The institutional momentum has been matched, almost serendipitously, by expanded connectivity: JetBlue, American, and Breeze have recently introduced direct service from New York, Boston, and Charlotte.
Defined by Old Florida elegance and generational loyalty, Vero Beach is evolving with fresh clarity in its cultural identity—one that feels timeless and forward looking at once.
VERO BEACH MUSEUM OF ART
Anchoring this renaissance is the Vero Beach Museum of Art’s roughly $100 million “Museum in the Garden” expansion—one of the most ambitious cultural undertakings in Treasure Coast history. Ground was broken this past November on a project that will double exhibition
space, introduce purpose-built studios, expand the children’s Art Zone, and unveil a 350-seat auditorium, all situated along the Indian River Lagoon.
What distinguishes the initiative, designed by Allied Works in collaboration with Unknown Studio, is radical accessibility: the museum’s entire ground floor—galleries, interactive installations, café, and community rooms—will be free and open to the public.
The architecture is deeply site-responsive, incorporating indigenous sand and crushed shells into the building envelope while framing expansive lagoon vistas. With 1.5 acres of newly conceived courtyards and gardens, the museum is poised to become one of South Florida’s most important civic spaces.
RIVERSIDE THEATRE
Occupying the neighboring parcel within the city’s cultural corridor, Riverside Theatre holds a distinction that belies Vero Beach’s modest scale: it is the largest professional theater in small-town America, a designation earned over decades of producing critically regarded work for more than 100,000 patrons annually.
Under the leadership of new Executive Producer and CEO Jon Moses, Riverside continues to draw top-tier talent directly from New York’s theater district.
A comprehensive campus expansion is underway, introducing stateof-the-art backstage infrastructure, a new studio building to expand rehearsal and class space, and landscaped pedestrian zones to create welcoming outdoor spaces within the park setting for the entire community to enjoy. These enhancements will enable stage productions of greater technical complexity and scale while expanding its educational and community impact through partnerships with local organizations like Gifford Youth Achievement Center, Youth Guidance, Boys and Girls Club, Environmental Learning Center, and the Gifford Youth Orchestra.
MCKEE BOTANICAL GARDEN
McKee Botanical Garden has positioned itself at the vanguard of subtropical botanical science through its collaboration with Fairchild Tropical Botanic Garden’s Million Orchid Project—a landmark conservation initiative reintroducing endangered native orchids throughout South Florida. The partnership has elevated McKee’s international standing within the botanical community. This scientific rigor finds its aesthetic counterpart in the garden’s forthcoming Rizzoli monograph, slated for 2026, featuring the celebrated photography of Ngoc Minh Ngo.
Founded by Arthur McKee and Waldo Sexton and originally opened in 1932 as a roadside attraction, the garden—now listed on the National Register of Historic Places—has evolved into a nexus of botanical research and landscape preservation. First recognized by The Garden Conservancy in 1996 as a preservation project of national significance, McKee received the organization’s highest honor last year: the Jean and John Greene Prize for Excellence in American Gardening.
Written by guest columnist Irina Woelfle, founder of Let’s Talk Vero and Vero Minute.
Historic stone bridge at McKee Botanical Garden
“Singin’ In The Rain” on the Stark Stage at Riverside Theatre
Breaking Ground
NEW FITNESS & WELLNESS AMENITIES
Already known for its world-class sporting amenities, Windsor is increasing its efforts to create an unparalleled experience for its Members with a new suite of health, fitness and wellness offerings. The centerpiece will be a state-of-the-art 13,800-square-foot Fitness and Wellness Centre situated in the North Village, Windsor’s final neighborhood.
The North Village is being planned as a seamless extension of Windsor’s existing Village, with a heightened emphasis on nature and resident well-being. Only 34 homesites and six row houses will be built. Featuring 26.5 acres of preserved natural space, the neighborhood will offer an exceptional outdoor lifestyle with scenic trails, firepits, an observation tower, and a kayak launch with direct access to the Indian River Lagoon.
The Fitness and Wellness Centre, designed by Merrill, Pastor and Michael Architects, is prioritizing a strong connection to the outdoors by creating open, airy spaces with abundant natural light. Members will have access to dedicated studios for cardio, strength, and flexibility training, sauna and steam, as well as modern spa treatment rooms.
The new Centre’s robust menu of fitness classes, spa treatments, and elevated offerings including sound healing, will offer Members a complete, immersive wellness experience under one roof. Programming for the facility was led by Blue Spa Inc., a leading wellness design consulting firm known for its work on more than 400 prestigious projects, including hotels, resorts, clubs, and residential properties, in over 40 countries.
Among Windsor’s new recreational offerings will be dedicated pickleball and padel courts, two of the fastest-growing sports nationwide. Thoughtfully integrated into the serene natural surroundings of the existing Village, these courts will encourage an active lifestyle and healthy social interaction.
The pickleball and padel courts will open in spring of 2026. The Fitness and Wellness Centre, the first building to rise in the North Village, is expected to be completed in late 2027.
“These additions to our health and wellness offerings mark a meaningful new chapter in the Windsor legacy,” said Luke O’Boyle, General Manager of Windsor. “We’re excited to create spaces that support both physical and mental well-being, while honoring the natural environment, ensuring Windsor’s values endure.”
Bottom: Conceptual renderings of Pickleball and Padel Amenity with landscape buffer removed to show detail. Top: Amenity with landscape buffer
Windsor Welcomes
NEW GENERAL MANAGER LUKE O’BOYLE
As Luke O’Boyle steps into the role of General Manager at Windsor, he brings with him a forward-thinking perspective rooted in tradition, hospitality, and continuous improvement. He will lead all aspects of Windsor’s operations with an emphasis on preserving the Club’s distinctive character and high standards.
O’Boyle recognizes that Windsor already boasts a strong foundation.
His goal is to build on that by enhancing the Member experience through thoughtful innovation, strategic planning, and operational excellence. The Club’s reputation for personalized service is a cornerstone principle. Along with that, O’Boyle plans to explore opportunities to enhance management practices to reflect the evolving needs of existing and future Members. O’Boyle, who joined Windsor on July 1, reports directly to the Windsor Board.
A graduate of Widener University’s Hospitality Management program, O’Boyle has more than three decades of progressive leadership
experience in prestigious Clubs throughout the United States. He most recently served as the General Manager and CEO of the Chevy Chase Club in Chevy Chase, Md. Previously, he held positions with Shinnecock Hills Golf Club in Southampton, N.Y.; Greenville Country Club in Greenville, S.C.; Houston Country Club in Houston, Tex.; and Vicmead Hunt Club in Wilmington, Del. O’Boyle is a longtime member and past board member of the Club Management Association of America. In 2024, he served as chair on the National Club Association board.
As Windsor’s General Manager, O’Boyle will be in the unique position of helping to shape governance for the future as the community transitions away from private ownership to Member ownership within five years. Also energizing to O’Boyle is the opportunity to help Club employees reach their potential through his mentorship.
“I’m honored to join the Windsor community and look forward to fostering the Club’s deep commitment to excellence, culture, and its Members,” O’Boyle said. “Windsor has set a remarkable standard in private residential living, and I’m excited to work alongside its talented team to build upon that legacy.”
Fast Approaching
WINDSOR’S HIGH-GOAL CHARITY POLO CUP
As Windsor makes plans for its 2026 Charity Polo Cup, the enthusiastic response has been heart-warming.
Presented by PNC Bank, the much-anticipated event promises a fun day out for attendees while raising funds for three deserving local organizations: Childcare Resources, Crossover Mission, and the Environmental Learning Center.
Set for Saturday, February 14, the charity event features a world-class polo match, elegant fieldside luncheon, junior play match, themed tailgate, luxury automobile concourse, and an exciting silent auction and raffle.
Although many sponsorships and ticket options have already sold out, there are still opportunities to become involved in this worthy cause including a new Player Sponsorship level. Priced at $16,000, the Player Sponsorship includes a luncheon table for 10 and tickets to the Player Cocktail Reception on Friday night, a full-page advertisement in the Program, recognition by the match announcer and on signage, an exclusive meet-and-greet with the polo players, and more.
To promote a business or simply show support of the event beneficiaries, consider an advertisement in the event’s coveted official Program. Opportunities begin at $400. On the east side of the field, festive tailgaters will enjoy a front row seat to all the action, plus the chance to show off their creativity by participating in the optional Tailgate competition. Tickets are available at $600; each tailgate occupies up to six guests.
For the latest updates, check the website: windsorcharitypolocup.com
Luke O’Boyle
10500 Savannah Drive
6 BEDROOMS | 6 FULL, 1 HALF BATHS | $5,850,000
Beautifully situated along the western edge of the golf course in Windsor’s Central Village, this six-bedroom, six-bathroom residence embodies refined coastal living. A light-filled open floor plan unites the great room, kitchen, and family room, all framed by a white coffered V-groove ceiling and three sets of floor-to-ceiling French doors with transoms that open to an expansive loggia with panoramic lake and fairway views. The home centers on a landscaped entry courtyard with a fountain and dining loggia. A two-bedroom guest house with a private balcony offers sunset views and ideal accommodations for visitors.
Rana Begum: Reflection
OPENS IN JANUARY AT THE GALLERY AT WINDSOR
Celebrated British-Bangladeshi artist Rana Begum creates engaging sculpture, paintings and site-specific works that captivate with their luminosity, precision, and quiet power. Viewers often are entranced by her use of repetitive geometric patterns notable both in Islamic art and industrial cityscapes.
“Reflection,” an exciting exhibition by the London-based artist, will open at The Gallery at Windsor on January 24, 2026. Windsor’s show builds on Begum’s acclaimed U.S. Museum debut and marks her first presentation in South Florida.
Premiering at the SCAD Museum of Art in Savannah and traveling to Vero Beach, the exhibition will be displayed in two distinct cultural settings, each offering a unique perspective on Begum’s practice. Reimagined within The Gallery at Windsor’s distinctive architectural space and tropical outdoors, the show will span more than a decade of Begum’s practice, tracing her expansion of abstraction and Minimalism through a contemporary global lens. Known for her innovative use of industrial materials including automobile light reflectors, glass and metal panels, and chain link fencing, Begum transforms everyday objects into evocative compositions that exist in dialogue with their environment.
Windsor’s coastal setting and distinctive New Urbanist architecture— inspired by Savannah’s historic streetscapes along with the building traditions of the American South, Europe, and the Caribbean—provides a striking context for Begum’s vibrant works.
On view through May 8, 2026, “Reflection” invites visitors to experience Begum’s practice as a journey of discovery, where vibrant compositions evolve with each change in light or movement, expanding from aesthetic encounters into profound moments of contemplation. Begum’s work has been exhibited internationally in solo and group exhibitions, earning acclaim for its immersive, transformative qualities.
“Rana Begum uses light, space, and color to create profoundly transformative experiences for viewers,” said Daniel S. Palmer, Chief Curator of the SCAD Museum of Art and curator of Windsor’s exhibition. “Her work is so precisely calibrated that when we encounter it, fascinating perceptual effects unfold, inviting us to look more closely, to see subtle shifts and radiance, and ultimately to perceive the world around us in a completely new way.”
The Gallery at Windsor is open to the public by appointment. For more information, visit windsorflorida.com/gallery.
Portrait and installation photography Rana Begum: Reflection, 2025. Courtesy of the SCAD Museum of Art
