Inside the Isleworth Sculpture Collection: Moore, Dali, and Jackson in Windermere
Henry Moore, Salvador Dali, and Philip Jackson works line the streets of one of Orlando's most exclusive private communities — here's what residents actually live with.
The Isleworth sculpture collection is a private display of monumental works by Henry Moore, Salvador Dali, Philip Jackson, and Arturo Di Modica, located inside Isleworth Golf & Country Club, a 600-acre gated community at 6100 Payne Stewart Drive in Windermere, FL. The pieces are part of The Lewis Collection, assembled by Isleworth owner and British financier Joe Lewis, who acquired the community in 1993. The sculptures line the streets and fairways of the community and are only viewable by members, residents, and their guests. A publicly accessible rotation of works from the same Lewis Collection is displayed at the Lake Nona Sculpture Garden in southeast Orlando, roughly 30 minutes from Isleworth.
Here's something most people moving to Orlando don't realize: one of the most significant private sculpture collections in the Southeast isn't in a museum. It's scattered along the streets and fairways of a gated community in Windermere, where Henry Moore bronzes sit a short walk from a cast of Wall Street's Charging Bull and masked Philip Jackson figures keep watch over manicured landscapes.
This is the Isleworth sculpture collection. Let's be real about what it is, what it isn't, and why it matters for anyone thinking about life in Orlando's most rarefied zip code.
A Private Gallery, Not a Public One
First, the honest bit. The Isleworth sculpture collection is not public art. Isleworth is a private, gated country club community on the Butler Chain of Lakes, and the sculptures live inside the gates — along the entry drives, between holes on the championship golf course, and anchoring landscape moments throughout the 600-acre property. If you are not a member, a resident, or a guest of one, you cannot walk up and see them.
That's an important distinction, because "sculpture by Henry Moore" usually conjures up the experience of wandering a park or sculpture garden. Isleworth's collection is different. It's a perk of ownership — arguably one of the more unusual lifestyle amenities in American residential real estate. Living here means your morning jog, your commute to the Dr. Phillips dinner reservation, or your drive to the clubhouse all happen past works that would be featured in any major museum's permanent collection.
The Lewis Collection: How the Art Got Here
The sculptures are part of The Lewis Collection, named for British financier Joe Lewis, who acquired Isleworth in 1993. Lewis — founder of the Tavistock Group and a serious art collector — used his ownership of Isleworth as the stage for an outdoor collection of monumental works. Pieces rotate between Isleworth, Albany in The Bahamas, and the Lake Nona Sculpture Garden, all Tavistock-connected properties. This is why the artist list reads like a greatest-hits of 20th and 21st century sculpture.
The Artists You'll See
Henry Moore (1898–1986)
The British sculptor whose abstract, semi-figurative bronzes defined mid-century modern sculpture. Moore's work is in the permanent collections of the Tate, MoMA, and the National Gallery of Art. Isleworth is one of a handful of private U.S. sites where multiple Moore bronzes sit together outdoors.
Arturo Di Modica's Charging Bull
Yes, that Charging Bull. Di Modica created the original bronze that now stands on Wall Street in 1989, and Isleworth holds one of the few authorized casts — positioned between the first and tenth tees of the golf course. Other casts live at Albany in The Bahamas and at the Lake Nona Sculpture Garden. Moore himself nicknamed Di Modica the "young Michelangelo."
Salvador Dali (1904–1989)
The Spanish surrealist's sculptural output is less famous than his paintings but unmistakably his — melting forms, elongated figures, the same dreamlike vocabulary that made The Persistence of Memory iconic. Central Florida has a strong Dali connection through the Salvador Dali Museum in St. Petersburg; Isleworth brings Dali closer to home.
Philip Jackson (b. 1944)
The Scottish sculptor is Royal Sculptor to Queen Elizabeth II and the artist behind the Bomber Command Memorial in London's Green Park, the Bobby Moore statue at Wembley, and the Queen Elizabeth equestrian statue in Windsor Great Park. Jackson's signature — hooded, masked figures with textured lower bodies and precisely modeled hands and faces — appears across Isleworth's landscape. Fun trivia: early in his career, Jackson worked for Henry Moore. The Isleworth collection is, in a small way, a family reunion.
The Lake Nona Connection
If Isleworth's collection is behind a gate you can't pass, the Lake Nona Sculpture Garden is publicly accessible and displays rotating works from the same Lewis Collection. Past exhibits have included Moore's Mother and Child and Upright Motive No. 9, Fernando Botero's Leda and the Swan, Eric Goulder's Post Modern Man, and another Di Modica Charging Bull. Both properties are Tavistock developments, so pieces move between them. From Isleworth to Lake Nona is roughly 30 minutes via the 528.
Why This Matters for Orlando Real Estate Buyers
For buyers, the collection is a small but telling detail about what Isleworth is trying to be. This is not a gated subdivision with an entry monument and call it a day. The Lewis Collection signals cultural ambition as part of the community fabric — alongside the golf, Butler Chain access, security, and neighbor profile (past and present residents have included Tiger Woods, Shaquille O'Neal, and a roster of PGA Tour pros).
The Pros
- Genuinely significant outdoor art as part of daily life, not a museum field trip
- A curated residential environment managed to a consistent high standard
- Proximity to the Dr. Phillips restaurant scene, the Butler Chain, and Disney (15 minutes) without being inside any of them
- High-end neighbors and strong long-term value performance in the Windermere submarket
The Cons
- Entry price is steep — Isleworth homes routinely transact at $3M to $20M+, with initiation fees and carrying costs to match
- The privacy that protects the collection also protects you from casual guests — this is not a drop-in community
- You'll never bring a group of friends to "tour the sculptures" — this isn't a cultural asset you can share publicly
Where Isleworth Sits in the Windermere Landscape
Isleworth occupies a prime stretch of the Butler Chain of Lakes, the 11-lake system that defines Windermere geography. The community is minutes from Dr. Phillips to the east, Gotha to the north, and Horizon West to the southwest. Downtown Orlando is about 15 miles northeast; Walt Disney World is about 15 minutes south via Winter Garden Vineland Road and the 429.
For buyers who want the Windermere lifestyle without Isleworth's price tag or privacy trade-offs, the surrounding communities offer Butler Chain access, top-rated schools, and the same general geography. But none of them have the collection.
What the Locals Know
The Isleworth sculpture collection is one of those Orlando details that insiders mention casually and visitors learn about by accident. It lives behind the gate, as part of the daily texture of life for a few hundred very fortunate households.
If you're shopping Isleworth, the art is a genuine differentiator — not the reason to buy, but a meaningful expression of what the community is. If you're not shopping Isleworth but you love the work, head to Lake Nona. Same collection, different door.
For more information about the community, membership, and homes, visit Isleworth Golf & Country Club.
Curious about Windermere-area luxury homes or the communities that border Isleworth? Explore Dr. Phillips, Gotha, and Horizon West, or contact us for personalized advice on Central Florida's most exclusive neighborhoods.
