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The following year, she snapped up another three properties for approximately 49 acres with a price tag of more than $8 million combined. At the time, some of her properties had buildings on them while others didn’t. One such building is a ranch that Winfrey transformed into an inviting, island farmhouse with the help of decorator Ellie Cullman. While the project started as a small renovation, it quickly turned into a major project. Architect Jeff Wooley helped alter the floor plan, raise the primary bedroom ceiling, install French doors, and add a wraparound porch. The interiors were refreshed with a bright, breezy color palette and countryside-inspired fabrics and motifs.
Who are Oprah’s notable neighbors in Montecito?
And Oprah, ever the philanthropist, didn't take the money and run. Instead, she donated all proceeds to The Oprah Winfrey Leadership Academy Foundation, which funds girls' education in South Africa. On Sundays, she would travel with her father to “rich white people’s neighborhoods” to admire the grand houses there, and she began to build fantasies about how she wanted to live someday.
For Oprah, Home Is Where the Trees Are
It offers a serene environment away from the hustle and bustle of city life. The region is also a preferred location for many celebrities due to its exclusivity and the luxurious lifestyle it offers. Montecito, often referred to as the American Riviera, is a serene and picturesque enclave nestled between the Santa Ynez Mountains and the Pacific Ocean. Its Mediterranean climate, combined with its lush landscapes and pristine beaches, makes it a sought-after destination. For Oprah, Montecito offers a tranquil escape from the bustling media world.
Oprah's country estate in The Aloha State, which she completely gutted
So we're guessing she knew she wouldn't be spending a ton of time here. In typical Florida style, it included furnishings in neutral colors, palm-themed fans, and appliances that the typical American has in their apartment — no top-of-the-line fixtures here. It even had some odd touches — for example, one entire kitchen wall was coated in mirrors.
The Italian Opera House and Palmo’s Opera House (below) were the two first purpose-built opera houses, meaning, designed and used specifically for opera. Prior to that, there were other venues used for opera, which included Castle Clinton and Niblo’s Garden. These early opera houses, though interesting historically, were not successful, mainly because they failed to cater to the right crowds. Winfrey still owns a number of other properties, including her primary residence at a massive 20,000-square-foot mansion set on a 66-acre estate dubbed “Promised Land,” also located in Montecito. Self-made media mogul and all-around icon Oprah Winfrey sold a sprawling $14.8 million Mediterranean-style Montecito mansion to fellow A-lister Jennifer Aniston, Dirt reports. The sale marks the latest big-name real estate transaction in the rather star-studded coastal town, where celebs like Ellen Degeneres and Ariana Grande have made high-profile dealings.
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Per The Wall Street Journal, she dropped another $11 million on 60 acres of vacant space in Telluride in 2014. Oprah simply saw the space — and its crazy views of the mountains beyond — so she made the owner an offer they couldn't refuse, reported Haute Residence. As the biggest property in the area (which is also zoned for both a house and home for visitors,) we're guessing that Oprah planned to build another dream ski home here.

Camp Cope - Live at Sydney Opera House (
A custom-built staircase leads to the upper level, where you’ll find a huge bonus room/additional living room, as well as a decked out game room. And of course, a bathroom for easy access during Oprah’s all-nighters playing pool. Maybe we’re biased, but after our last visit in May, there is no doubt Orcas Island is where it’s at, y’all. Oprah Winfrey is one of the most successful and wealthiest people in the world, so how did she manage to achieve such fame and success?
The Impact of Oprah’s Home on Montecito’s Real Estate
She began working in media at a mere 17 years old and slowly worked her way up, until she finally became the host of the iconic "Oprah Winfrey Show" in 1986. Her most recent purchase was in 2023 when she bought a whopping 870 acres for nearly $6.6 million in Kula, which is located in the Upcountry region of Maui. Around the same time she was purchasing the last of the four adjacent condos in Water Tower Place, Winfrey also dropped $100,000 on a three-bedroom apartment at the Four Seasons Chicago.
The Outdoor Smoker
In his new book, The Space That Keeps You, interior designer Jeremiah Brent asks Oprah what her Montecito sanctuary means to her. Oprah’s home is a reflection of her journey, preferences, and values. This personal touch makes the mansion feel like a home rather than just a property. It’s a testament to how personal history and preferences can be infused into home design, giving it character and warmth. The new and improved abode features multiple french doors that open onto the porch and balcony, providing numerous opportunities to step outside and enjoy a gorgeous view of the ocean and surrounding property. Oprah’s Emmy Award Winning show Super Soul Sunday on the Oprah Winfrey Network was filmed under the massive oak trees located on this very property.
Oprah Winfrey to exit WeightWatchers board, a blow as weight-loss drugs surge - The Washington Post
Oprah Winfrey to exit WeightWatchers board, a blow as weight-loss drugs surge.
Posted: Thu, 29 Feb 2024 08:00:00 GMT [source]
Watch livestreams of new performances, highlights from the multi-genre archive, presentations by local and international performing arts companies, and original content created exclusively for the platform. After eight years crafting fearless, empowering anthems that shook up Australian music, beloved Melbourne trio Camp Cope signed off with a final farewell show at the Sydney Opera House Concert Hall in October 2023. Enjoy a selection of songs from the part rock opera, part reimagined pride parade which presented a 4 hour, 55 original song performance live from the Concert Hall stage. Watch the renowned Jamie Oliver's Australian exclusive conversation with Melissa Leong. The historic Jones Bay Wharf is another familiar filming location in Anyone But You.
Over the next decade, Maude Adams performed the role more than 1,500 times. One of those performances was at the San Bernardino Opera House on April 19, 1913. After Waters’ death in 1889, his daughter, Martha L. Kiplinger, continued on as the manager. She immediately began booking traveling shows to appear, and by the turn of the century the big-time entertainers came. If you lived in this area during the early 20th century, you didn’t need to travel far to see the great stars of the theatrical world. The material on this site may not be reproduced, distributed, transmitted, cached or otherwise used, except with the prior written permission of Advance Local.
The town’s charm lies in its tree-lined streets, historic estates, and the sense of community it fosters. It’s a place where Oprah can find solace, rejuvenate, and be close to nature. Emma Farrow is an experienced copywriter, social media fanatic, and beauty-loving gal.
Given the appreciation of real estate, especially in sought-after areas like Montecito, and the “Oprah effect” on property values, the estate is likely worth significantly more today. While many celebrity homes come with standard luxury amenities like pools, home theaters, and gyms, Oprah’s Montecito house has some unique features. The tea house overlooking the serene pond, the outdoor fireplace pavilion, and the hand-carved tubs are just a few elements that set her home apart. These features, combined with the property’s historical significance and architectural marvel, make it truly one-of-a-kind. The master bedroom, a spacious haven, offers breathtaking views of the Montecito landscapes. Every detail, from the luxurious bed linens to the personalized decor, reflects Oprah’s personal style and preferences.
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