According to Deadline, Oprah owns a $100-million property with a private road that runs inland, connecting the beachfront area of Wailea to the elevated location of Kula. Oprah, who has a reported net worth of $3.2 billion, has reportedly lived part-time in Hawaii since the early 2000s and owns over 2,000 acres of land in Maui, specifically.

Oprah Winfrey's representative and the president of Haleakala Ranch confirmed that a private road on Maui is owned by the ranch and not Winfrey.