From Hawai’i to Colorado to California, Oprah Winfrey has been steadily expanding her real estate empire for decades.
Since the 1980s, the media mogul has been building an impressive portfolio of properties, and as of 2025, she owns over 1,100 acres across three states, according to Realtor.com.
The 71-year-old recently faced intense backlash online after reports claimed she refused to open a private road connecting Wailea to Kula, Hawai’i during tsunami warnings on Tuesday, July 29. The controversy reignited public debate about just how much land Winfrey owns.
Social media was flooded with calls for Oprah to “open the road,” as frustrated users highlighted the issue across multiple posts.
Oprah Winfrey currently owns about 1,000 acres in Maui, where she began buying property back in 2003. Her first purchase included two properties in the Kula community for $5.3 million, and she’s been a part-time resident of the island ever since.
Over the years, she’s continued to expand her holdings, acquiring 163 acres for more than $40 million and another 870 acres of agriculturally-zoned land for $6.6 million.
While some locals have voiced concerns over celebrities buying up large swaths of land, Maui council member Yuki Lei Sugimura praised Winfrey for supporting the community. “We’re struggling, we’re putting tax dollars together to try to do fencing and culling,” Sugimura told KITV4. “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 her extensive land ownership in Hawai’i, Winfrey’s primary home base is in Montecito, California. She moved to the Central California enclave in 2001 after purchasing a 40-acre property for $50 million. She later expanded her estate by buying a neighboring equestrian property for $28.85 million in 2015 and Jeff Bridges’ nearby retreat for $6.85 million in 2019.
Winfrey also owns 66 acres in Telluride, Colorado, which she purchased in 2014 for $10.85 million. While she had plans to build a custom home on the property, she bought a high-tech $13.7 million house nearby in the meantime.
