The celebrities and the superrich who live in Isleworth, including Tiger Woods, would like to project a common touch. Every Halloween, residents of the gated golf community near Orlando, Fla., decorate their golf carts and drive trick-or-treaters door-to-door. They share lunches and dinners at the country club, play pickup basketball games and hold community events. “It’s pretty normal,” says Rav Mehta, CEO of a software-development firm who lives just outside Isleworth’s vine-covered walls but has many friends inside.
Normal is a relative term. Houses inside Isleworth’s 600 acres , 45 miles southwest of Orlando, Fla., cost between $2 million and $8 million. Aside from Woods, perhaps the wealthiest and most famous golfer in history, homeowners have included sports legends like NBA superstar Shaquille O’Neill, movie stars like Wesley Snipes and tycoons like Planet Hollywood creator Robert Earl. The development is ranked the world’s No. 1 luxury golf community, and the Mediterranean-style country club is a massive 89,000 square feet . Isleworth has its own private security force with marked patrol cars and fully staffed guard houses that carefully screen any visitors. Even police officers from the nearest incorporated town, Windermere, must ask permission to enter.