Oprah Buys More Property on Maui

By Duane Shimogawa
Special to Maui Now

Oprah Winfrey is back again at shopping for Maui real estate, as the billionaire media mogul has recently purchased a three-acre property in Kula on Maui that’s adjacent to the other properties she owns on the Valley Isle, according to public records.

The television star, who has her own TV network, already owns more than 100 acres in Kula that is occupied by her modern-style farmhouse.

Winfrey paid $7 million for her latest purchase on Thompson Road, which includes a 1,139-square-foot building on the property. The three-acre agricultural-zoned property has a total assessed value of about $416,800, tax records show.

The sellers purchased the property in 1974 for $50,000, making it a 14,000% profit for the sellers.

The deal, which closed on Oct. 18, shows the buyer as Madrona Tree LLC that lists Cindy Iwaki, an executive of Winfrey’s companies, as its manager, according to the sales deed obtained by “Shimogawa Scoops.”

Winfrey owns the other adjacent parcels of land in “Upcountry” Maui through her other entities such as OW Ranch LLC, Oprah’s Farm LLC and Yellow Brick Road LLC. 

Her former personal trainer Bob Greene also owns property in the area. He originally was the inspiration behind Winfrey’s initial Maui purchases.

This recent purchase makes sense since it allows her to connect many of her properties in the area.  There are still other adjacent properties in the area that is owned by others.

Winfrey, who has been a part-time Maui resident for more than 15 years, recently made headlines in Hawaiʻi for her foundation’s support – in the form of a $100,000 grant – of the Women’s Fund of Hawaiʻi, a nonprofit aimed at furthering the growth of women and girls.

Meantime, Amazon founder and executive chairman, Jeff Bezos reportedly purchased a remote 14-acre oceanfront estate recently, at La Perouse, Maui.