John Malone – Sampson Cay, Price Undisclosed
John Malone made billions as a CEO and landowner. Currently, the chairman of Liberty Media and Liberty Global, as well as CEO of Discovery Holding Company, he is also regarded as the largest landowner in the United States.
He stayed true to his reputation and bought one of the biggest private islands ever put up on the market. It was an open to the public resort with five villas, a restaurant, and a marina, but Malone closed the resort in 2013, opting to use it for private family vacations instead.
