Oprah Winfrey has purchased nearly $ 90 million in real estate on 67 acres in Montecito, California in the past few years, so it’s safe to say that her vast holdings exceed $ 200 million. And why not? She is the queen of all media and one of the most famous and recognizable people in the whole world. If I even had $ 1 billion, not to mention the $ 3.5 billion in Oprah, I would also build a complex-style fortress! Last fall, she expanded her estate (called The Promised Land, natch) by picking up Jeff Bridges’ Spanish renaissance house adjacent to the 67 acres it already owned. The former Bridges property sits next to Seamair Farm, a 23-acre lot that borders its 43-acre promised land estate. She bought Bridges’ house for $ 6.85 million.
Bridges listed the property for $ 8 million in March 2019. Oprah looked and waited for the price before buying it for exactly what Bridges paid for the house in 2014. It seems that Oprah doesn’t want neighbors (and can you blame her?). Overall, this piece of land and the buildings therein are worth north of $ 100 million, with Winfrey owning seven homes from California to Maui to Washington State.
First, let’s look at the houses that Oprah no longer owns. From 1985 to 2015 Oprah’s the primary residence was a 9,625 square foot house in Chicago which it sold in 2015 for $ 4,625 million. That same year, she also sold a colonial-style home on the outskirts of Elmwood Park for $ 375,000 and a 10,000 square foot duplex just north of downtown Chicago for $ 4.6 million. In 2012, she sold her cooperative in the Gold Coast district for $ 2.8 million. She also previously owned a penthouse in Atlanta which she sold in 2008 for $ 1.8 million.
Oprah has now solidified its base in Montecito. In 2001, Winfrey paid $ 50 million for a 23,000 square foot mansion on 42 acres in Montecito. The Neo-Georgian mansion is his main residence and alone is worth at least $ 90 million. The house has six bedrooms and 10 fireplaces. Add the neighboring 23-acre farm that Winfrey bought in 2016 for $ 29 million, and the former Bridges and Oprah estate has 67 adjoining acres with 13 separate buildings, two pools, ocean views, and a tennis court.
Oprah also owns a 43-acre estate on Orcas Island in Washington State that she bought for $ 8.275 million in 2018. In 2014, she spent $ 14 million on a ski chalet in Telluride, Colorado.
Oprah bought her first property in Maui in 2002. Over the years, she has spent up to $ 60 million to restore more than 160 acres in Maui. She spent $ 32 million in a single transaction to buy the neighboring property.
In total, Oprah owns hundreds (potentially over 1,000 acres) of real estate in the United States with a minimum value of $ 200 million.