Oprah Winfrey Buys 870 Acres in Maui

Oprah Winfrey has significantly expanded her real estate holdings in Hawaii.

The billionaire media mogul purchased a whopping 870 acres of land in several sales for a total of $6.6 million in the Kula area of the island of Maui, KITV4 reported.

Winfrey bought about 520 acres for $3.9 million and 330 acres for $2.5 million, from the seller, Hawaii-based Ulupalakua Ranch, Maui Now reported. She paid about $100,000 for the other 20 acres in separate transactions, the outlet said.

Winfrey, according to the outlet, already owned more than 1,000 acres of property in Kula and is one of the largest landowners on Maui, KITV4 and Maui Now said. She also bought 200 acres of land in Hana in the early and mid-2000s, Maui Now reported.

The land Winfrey recently purchased is zoned for agricultural use, KITV4 reported.

Winfrey, who has been a part-time resident of Maui for some 15 years, has filmed taking hikes with her friend, Gayle King, on the island, Maui Now said.

“Y’all should come here,” Winfrey wrote in a social media post, according to Maui Now. “Hashtag Hawaii, state of health. That’s the aloha spirit.”

Winfrey has been active with other real estate holdings, most recently selling a 4,300-square-foot Montecito home to Jennifer Aniston for $14.8 million in September.

Winfrey bought the “Tuscan farmhouse” in early 2021 for $10.5 million. The sellers were New York hedge fund manager Fred Shuman and his wife Stephanie, who had assembled the 2.1-acre spread.

Their complex included the Mediterranean-style villa, two small cottages and grounds.

Forbes has pegged Winfrey’s wealth at $2.5 billion. She owns numerous homes, including a $30+ million compound she bought in 2012 from Diandra Luker, the ex-wife of actor Michael Douglas, next door to Aniston’s new home.

But the main residence for the founder of the OWN network is the 66-acre “Promised Land” property in Montecito, anchored by a 23,000-square-foot neo-Georgian mansion.

Aniston’s main residence may be her mid-century modern home in Bel-Air, built in 1965 by architect A. Quincy Jones which she bought in 2012 for $21 million. It was featured in 2018 by Architectural Digest.

— Ted Glanzer