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As of 2023, it’s estimated the entertainment mogul now makes an annual income of $190 million. Oprah is the proud owner of a Volkswagen Beetle worth just over $25,000. Aside from her fleet of Cadillac Escalades fit with drivers who are at her every whim, Oprah recently bought a new Tesla.
Oprah's 60-acre property in Telluride where she planned to build (another) dream ski home
The opera house was built by mountain man-turned civic leader James W. Waters and his partner, Herman Brinkmeyer, as an investment in 1882. The beautiful red brick edifice with white facade topped by a golden eagle was known throughout the country for presenting top quality shows and concerts. Anyone But You was filmed in parts of Australia around New South Wales and Sydney. Director Will Gluck told The Hollywood Reporter that he wanted the film set in Sydney because he had “really fallen in love with the city” and liked it so much he moved his family there. Palmo’s Opera House was located on Chambers Street, between Broadway and Centre Street.
Oprah's Hawaii Home
Oprah spent all her years filming The Oprah Winfrey Show residing in Chicago. Having sold her Chicago Water Tower Place Complex in 2015 for $4.625 million, she then went on to purchase a $14 million ski chalet just a few months later. Also situated on the new addition, Oprah’s barns and stalls are likely an equestrian’s dream. The barn appears to hold at least a dozen horses in spacious, covered stalls. This is not the type of room you expect to see in a property estimated to be worth $90 million. Oprah feels the same way and added it to her list of rooms to redo.
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Set in the midst of Oprah’s Montecito garden, this building was originally meant to serve as a place to cut flowers. However, while watching the structure being built, Oprah changed her mind and decided to use it as a space for herself. Today, the building’s arched doorway is framed by wisteria, while an elegant copper fountain sits right out in front. As this new form of entertainment was really coming into vogue during the 1920s, San Bernardino was keeping up with the times. The creative genius of William Fox, the guru of the lavish Fox West Coast Theaters, was making his way throughout Southern California. If you purchase a product or register for an account through a link on our site, we may receive compensation.
She also made it clear that while she could conduct business meetings here, she will never do so. The path, which pays homage to her grandmother, is lined with thousands of white hydrangea bushes, much like the one that sat in front of her grandmother’s house while she was growing up. In addition to the hydrangeas, you’ll see pinkish-white Sombreuil roses climbing along the wrought-iron arches and white iceberg roses surrounding the statue. Depending on where she stands in the huge garden, she can take in picturesque views of the Pacific Ocean or the Santa Ynez Mountains. This picture gives you a better idea of what Oprah spent an additional $28.85 million to buy. Unfortunately, you can’t really see anything from the fruit orchard, except for the tops of the trees, but if you look at the top of the photo, you do get a glance at the equestrian ring.
However, it was more of a hidden gem, known to a select few who cherished its tranquility. Beyond the celebrity allure, Montecito offers a tight-knit community vibe. Local farmers’ markets, boutique shops, art galleries, and community events foster a sense of belonging. Oprah, with her philanthropic endeavors and community involvement, finds Montecito aligning perfectly with her values. The town’s emphasis on wellness, nature, and community engagement complements Oprah’s lifestyle, making it more than just a residence – it’s a home. No celebrity home is complete without dedicated entertainment spaces, and Oprah’s mansion is no exception.
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Who are Oprah’s notable neighbors in Montecito?

While there's no doubt that Oprah Winfrey's massive Montecito mansion is impressive, her other homes are just as enviable. Even though Oprah's Promised Land estate is astounding, it's not the only home in Montecito that she wanted to call her own. The price was exactly the same as when he bought it half a decade earlier. Winfrey set out to build a mountain hideaway when she purchased nearly 60 acres of land in the town of Mountain Village that borders the Telluride Ski Ranches area for $10.85 million. Unfortunately, she ran into a legal issue when a retired nuclear physicist sued her for trail access rights. “I don’t care if Oprah is a neighbor, but if she is going to cut off access to trails, I don’t find that acceptable,” the physicist told The Denver Post.
We were surprised but it was believable given that every time we visit the island there’s news of another big celebrity sighting and/or real estate deal. US Secretary of Defense Robert Gates, Condoleeza Rice, Josh Groban, Kat Dennings, the list goes on. It's also much more than a home — and a century-old home at that. The property that now belongs to Oprah includes lots of lush land, including gardens, several types of trees, and orchards. Plus, it's a paradise for an equestrian, since there are horse stables and a carriage house.
Oprah’s Dining Room
And so that’s why I called it that… because I think it’s a fulfillment of the promise that Dr. King spoke of.” Wise words from the media mogul herself. The property is also home to lots of gardens as well as avocado and fruit orchards. During our last visit, the rumor mill was working overtime thanks to news that Oprah and her “Live Your Best Life” partner in crime Bob Greene had purchased property on the island.
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"I love, love, love my house," Winfrey said of the Maui getaway in 2006. "It's a gem, so sweet and exquisite. Such a real, normal house. It feels like a nice blanket. A lovely and soft cashmere one." As of 2021, the mogul has amassed a net worth of $2.5 billion, according to Forbes, and has built an empire of philanthropy and media production and distribution. Given her many commitments, it makes sense that Winfrey has made homes for herself in numerous cities throughout the United States. Though Montecito, California, has been her main base for more than 20 years, Winfrey has also owned homes in Illinois, Florida, Hawaii, Colorado, and Washington state. She’s also owned, or currently owns, properties in Tennessee and Indiana, though she primarily purchased those residences for family and friends.
The renowned luxury hotel is situated just a few blocks from Lake Michigan and not too far from the Near West Side, where Harpo Studios, Winfrey’s multimedia production company, was located at the time. Winfrey ultimately sold this property for $1.275 million in 2015, the same year she closed the studios for good and relocated to the West Coast. One of the standout features of Oprah’s mansion is its harmonious integration with nature. The design emphasizes open spaces, large windows, and terraces that offer panoramic views of the surrounding landscapes.
The Academy of Music was located on 14th Street and Irving Place and catered to wealthy New Yorkers, who were migrating uptown. The construction cost of the building at the time was upwards of about $400,000. The Italian Opera House was located on the northwest corner of Leonard and Church streets in what we would know today as Tribeca. Architecturally, the Italian Opera House looked akin to a small White House. It was built by Venetian-American Lorenzo de Ponte, who was a Roman Catholic priest and librettist for Mozart. He emigrated to America in the late 1820s, became the first professor of Italian literature at Columbia University, and founded the Italian opera house in 1833, at the age of 84.
Just a year before Oprah's show first hit the air, she bought what would become the basis of her fabulous, customized duplex. She spent another $3.5 million on three other units throughout the years to create the enormous space. But the condo itself wasn't the only part of this property to hit the market. A few months later, in a sort of celebrity-esque estate sale, Oprah auctioned off tons of items in the apartment, including artwork and furniture, much of it antique, according to Page Six.
This seamless blend of indoor and outdoor spaces is a lesson in how modern homes can embrace nature, enhancing the living experience. The home was built in the late 1990s and boasts 4 beds as well as 4,320 square feet of interior luxury living space. It has a long narrow drive with red brick on either side leading up to the main entrance and is completely surrounded by beautiful trees and other lush green landscape. Oprah originally purchased the 42-acre estate for $50 million in 2001. (Today, it’s estimated to be worth $88 to $90 million, according to a 2012 tax assessment.) In 2016, she had the opportunity to purchase an adjacent 23.26-acre parcel of land, known as Seamair Farm.
Originally built in 1912, it has undergone numerous exterior and interior renovations over the years to get to the size it is today. Oprah hasn’t shown any interest in buying it, but you never know. Just a few days ago she sold the majority stake in OWN to the Discovery Network for $70 million, meaning she has more than enough cash laying around to purchase it (as if she didn’t already). If you weren’t already jealous enough, it is time to take an up-close look at Oprah shares with her beloved dogs. However, it’s her large estate in Montecito, often referred to as the Promised Land, where she can most often be found. WASHTENAW COUNTY, MI -- Lauren Wagner once sang before thousands in full auditoriums around the world, but the 70-year-old now shares her love of music within the walls of her senior living home near Saline.
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