Thursday, January 6 2022

Oprah Winfrey speaks at “Live Your Best Life” in Maui. PC: Wendy Osher / Maui Now (2017 file)

By Duane Shimogawa
Special in Maui now

Oprah Winfrey is back to buying Maui real estate as the billionaire media mogul recently purchased a three acre property in Kula on Maui which is adjacent to other properties she owns on Valley Island. , according to public records.

The TV star, who has his own TV network, already owns over 100 acres in Kula which are occupied by his modern-style farmhouse.

Winfrey paid $ 7 million for his latest purchase on Thompson Road, which includes a 1,139 square foot building on the property. The three-acre farm property has a total estimated value of around $ 416,800, according to tax records.

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


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


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

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

This recent purchase makes sense since it allows him to link several of his properties in the region. There are still other adjacent properties in the area which are owned by others.


Winfrey, who has lived in Maui part-time for over 15 years, recently made headlines in Hawai’i for her foundation’s support – in the form of a $ 100,000 grant – to the Women’s Fund of Hawai. ‘i, a non-profit organization aimed at fostering the growth of women and girls.

Meanwhile, Amazon founder and chief executive officer Jeff Bezos reportedly recently purchased a remote 14-acre beachfront estate in La Perouse, Maui.

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