Isleworth

Isleworth is one of America's most exclusive private gated communities — a 600-acre island enclave on the Butler Chain of Lakes in Windermere, Florida, founded by Arnold Palmer in 1984 and built around the championship golf course Palmer designed (opened 1986). With only 360–380 estate homesites, an invitation-only Country Club, and a long history of high-profile residents — Tiger Woods, Shaquille O'Neal, Wayne Gretzky, and others have called it home — Isleworth operates more like a private members' club than a typical neighborhood. Homes occupy lots ranging from half-acre patio estates to 14-acre lakefront compounds, with floor plans from roughly 2,800 to over 16,000 square feet. There are no townhomes, villas, or condos — just custom single-family estates, designed and built by Florida's top luxury custom builders (Goehring & Morgan, McNally, Akers, Waters, and others). New construction is rare; the community is essentially built out, so activity is mostly resales and the occasional teardown-rebuild on a premium lot. Recent twelve-month average selling prices have run around $5.35 million, with verified 2024–2026 sales spanning $3.55M to over $9M, and current listings pushing into double-digit millions. The Country Club centers on an 89,000-square-foot Mediterranean clubhouse staffed by 200+. Members access a 7,544-yard Arnold Palmer course, a Golf Performance Center with two hitting bays and pro instruction, six Har-Tru clay courts plus a Plexicushion hard court and a padel court, a state-of-the-art fitness center, an infinity-edge resort pool with a children's splash pad, the Spa at Isleworth, and four dining venues from formal rooms to a poolside grill. Private member docks open onto the 13-lake, 5,000-acre Butler Chain — making waterskiing, paddleboarding, fishing, and Disney-fireworks-from-your-boat part of daily life. Year-round programming runs from Summer Camp Isleworth for kids and grandkids through holiday galas, charity events, and resident-led clubs. Membership at the Country Club is by invitation, with full-golf initiation reported above $100,000 and annual dues around $30,000. Membership is not required for home ownership — many residents hold social-only memberships or none at all — and there's a current waiting list. The HOA fee is approximately $2,589 per quarter (~$863/month), covering 24-hour gated security, gates, common-area landscape, and the community's lakeside trails and parks. There is no CDD, which saves Isleworth buyers thousands per year compared with newer FL master-planned communities. The vibe is unmistakably ultra-high-net-worth and intentionally quiet. The gates and the membership process create a double-screen of privacy, and residents value the absence of paparazzi-style attention even as the community has hosted some of the most-photographed athletes and entertainers in the world. The atmosphere is family-friendly inside the gates — kids' camps, holiday events, summer programming — but the broader culture is reserved, golf-centric, and lake-focused. Geographically, Isleworth is hard to beat: 6 miles to Disney World (10–15 minutes), 22 miles / 25–30 minutes to MCO, 15–20 minutes to downtown Orlando, 10–15 minutes to Universal, and a short drive to Restaurant Row. Orlando Health and AdventHealth campuses are within 20 minutes. Despite the exclusivity, daily errands are easy — Publix and shopping in Windermere are just outside the gate.