From Hawai’i to Colorado to California, Oprah Winfrey has been building out her empire since before the turn of the century.
Much like her success in entertainment, Winfrey has been expanding her real estate portfolio since the 1980s. As of 2025, she owns over 1,100 acres across three states, as reported by Realtor.com.
Winfrey, 71, faced heavy online criticism after reports surfaced that she refused to open her private road connecting Wailea to Kula, Hawai’i during the tsunami warnings on Tuesday, July 29 — a controversy that reignited public focus on just how much land the billionaire media mogul owns.
Calls for Oprah to “open the road” were made on several posts shared on social media.
Winfrey currently owns about 1,000 acres in Maui, where she first began putting down roots in 2003. She first purchased two properties in the Kula community for $5.3 million and has been a part-time resident ever since.
Over time, she has continued to accumulate land on the island, purchasing 163 acres for over $40 million. She also purchased 870 acres of agriculturally-zoned land for $6.6 million.
While some locals have pushed back against celebrities coming in and purchasing large amounts of land, KITV4 spoke with Maui council-member Yuki Lei Sugimura, who gave praise to Winfrey for hiring locals and keeping the land undeveloped.
“We're struggling, we're putting tax dollars together to try to do fencing and culling," Sugimura said. "We want to protect our food for food security as well as protect the watershed. Those are the big issues and [Winfrey's] stepping right into them.”
Despite owning so much land in Hawai’i, it seems that Winfrey’s primary place of residence is in Montecito, California. She moved to Central California in 2001, with a $50 million purchase of a 40-acre property. She also purchased a neighboring equestrian estate for $28.85 million in 2015, and actor Jeff Bridges’ retreat nearby for $6.85 million in 2019.
Winfrey also owns 66 acres of land in Telluride, Colorado, which she purchased in 2014 for $10.85 million. She had plans to build a custom home on the property, but in the meantime, purchased a high-tech $13.7 million house nearby.