Exploring Oprah Winfrey's Luxurious Montecito Estate

Table Of Content

• Winfrey Sets Her Sights on California and Snaps Up a Chicago Property
• Seamair Farm Estate
• Oprah’s Tea House
• Is Oprah Buying the Whole Island?
• Future Islands - Live at Sydney Opera House (
• ‘Rivers in the sky’ have drenched California, yet even more extreme rains are possible
• The Kitchen That Doubles as a Filming Location

The tea house is a gazebo of sorts, located just outside the main house and overlooking the East Sound. All 4 walls are made up of windows and it’s surrounded by a patio, with a firepit of course. Located on the Eastern coast of Orcas Island’s East Sound sits the 41-acre estate known as Madroneagle – now known as the Oprah house! The sprawling property is home to the Madromeagle Estate, a tea house, a custom sauna, a barn/workshop, an underground hut, a craft shed, among others. Oprah's interior decorator and architectural designer made the place into an entirely new home — one that's reminiscent of a country estate rather than a tropical compound. Oprah's team decorated with lots of classic, 19th-century antiques to fill the space, like folk art of American farmers, a lamp shaped like a rooster, and a weather vane designed to look like a horse.

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Winfrey Sets Her Sights on California and Snaps Up a Chicago Property

It also included two cottages and gardens across just over two acres. In 2022, she sold the main home to Jennifer Aniston for $14.8 million. According to the New York Post, Winfrey sold the other part with two cottages on it to her personal trainer and property manager, Bob Greene, for $2.3 million. In May, 2018, Velvet Ropes broke the story that Oprah had purchased a sprawling waterfront estate on Washington State’s Orcas Island for $8.28 million. Named The Madroneagle Estate, this super secluded compound has 4-bedrooms, 3-full bathrooms, 2-half bathrooms, and boasts 7,303 square feet of luxurious living space. (But why wouldn't you if you're worth $2.5 billion?) Per Berg Properties, she also owned a 4,800 square foot penthouse apartment in Atlanta, Georgia, that she paid more than $1.5 million for when she bought it in 2003.

Seamair Farm Estate

The Astor Place Opera House debuted on November 22, 1847 with a performance of Giuseppe Verdi’s Ernani, which was very well-received and very well-reviewed. Later on, the Astor Place Opera House debuted Verdi’s Nobuko in 1848. Verdi’s operas, and five other operas will have their American debuts at the Astor Place Opera House. The opera house will however become infamous in New York City history because of the riots that took place there, one of the deadliest in New York City history. The property, which is zoned for agriculture, also came with a 1,139-square-foot building, according to Maui Now.

Oprah’s Tea House

As you step inside, the expansive living spaces captivate the senses. High ceilings, adorned with exquisite chandeliers, and marble floors reflect the sunlight pouring in from the large windows. The living rooms, with their plush sofas and handpicked artifacts, exude warmth and luxury, making them perfect for both relaxation and entertaining guests. Oprah’s Montecito mansion is nothing short of an architectural masterpiece. The mansion, designed with a mix of Georgian and Neo-Classical styles, boasts of high ceilings, spacious rooms, and intricate detailing.

Is Oprah Buying the Whole Island?

With the influx of celebrities like Ellen DeGeneres, Rob Lowe, and Prince Harry and Meghan Markle, Montecito’s real estate scene is set to remain robust. The demand for luxury properties with privacy and unique features will continue to grow. As Montecito solidifies its reputation as a celebrity enclave, property values are predicted to rise, making it a lucrative investment for potential buyers. Upon entering Oprah’s mansion, one is immediately greeted with a sense of opulence and grandeur. The main entrance, adorned with intricately designed double doors, sets the tone for the rest of the home.

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Winfrey also bought a surprisingly modest four-bedroom, Colonial-style home in Chicago’s Elmwood Park suburb for just $298,000. She renovated the 1941 property, updating the not-so-glamorous features like the roof, gutters, and garage door along with the home’s heating and cooling system. Considering how well-traveled Winfrey is, with personal and business connections all over the country, it's no surprise the former talk show host has put down roots in multiple locations. For the past two decades, Montecito, California, has remained her main hub. But the multi-hyphenate has also owned homes in nearly every region of the United States, with properties in Illinois, Florida, Hawaii, Colorado, and Washington state. We've gathered the highlights of her vast real estate portfolio below.

At first, the founders hoped to make the venue less stuffy than the Astor Place Opera House, but they failed at that almost immediately. The debut opera was Vincenzo Bellini’s Norma and The Academy of Music became an institution overnight. It was a versatile space that could be used not only for opera, but also for balls and receptions. Notable patrons included the Prince of Wales, Abraham Lincoln, and his wife Mary Todd. It was a place to see and be seen, with the patrons much more interested in observing each other than watching opera.

DeCoite also noted that "much of the land" Winfrey has purchased has remained undeveloped. According to Maui Now, Winfrey bought "more than 200 acres of coastal land in Hāna" through 2005. It is unclear what the land is used for, and she did not respond to Insider's request for comment about its status. In March 2023, Maui Now reported that Winfrey spent $6.6 million on 870 acres of land in Kula. Billionaires have previously faced criticism from locals for making big land purchases in Hawaii, saying they are pushing up the cost of property and pricing out locals, Forbes reported. As Insider previously reported, Winfrey owns an estate in Montecito, California, which she bought for $52 million in 2001, as well as a duplex in Chicago, a home in Antigua, a ski chalet in Telluride, Colorado, and more.

And, it was specifically designed for people to watch each other, with what was known as the “Golden Horseshoe”—two levels of ornately decorated boxes. It fell victim to fire in 1892 but was rebuilt by Carrère and Hastings, who also designed the New York Public Library, to make it even more golden than before. Even so, the Old Met will face the chopping block in the mid-20th century, a story detailed in both the podcast in a previous article. Perched on a cliffside overlooking the private beach is the guest house, which the previous owners named The Gallery House. To me, a guest house is a one-room shack and a futon…for Oprah, it’s a 4 bedroom, 3 bathroom, 2,948 square foot palace. The main level houses the kitchen, the living room, dining area, and bedrooms.

After getting her start in talk show hosting in the late 1970s, Winfrey went on to host a morning talk show in Chicago that was eventually renamed The Oprah Winfrey Show. Since The Oprah Winfrey Show's initial airing in 1986, the TV program ran for 25 seasons until 2011. The show is still one of the most highly rated daytime talk shows ever, and it made Winfrey a household name as well as a very rich lady. A man living nearby launched a lawsuit against Oprah, claiming that the home would inhibit his rights to access the trails, said The Denver Post. He ended up dropping the suit, but it doesn't seem to have mattered much. She moved at age 6 to live with her mother, inhabiting a “series of bad walk-up spaces,” whatever they could find and afford while living on welfare.

There’s no word on what Oprah plans to do with the equestrian ring or stables, but she’s never really shown any interest in horses in the past. Keep in mind that Oprah is notoriously private when it comes to her home, so finding pictures of it, particularly the interior, isn’t easy. (At a recent event, she admitted that she rarely opens up this space because “shutterbugs disrupt privacy”.) With that being said, here are 20 amazing photos of Oprah Winfrey’s amazing Montecito home. Seeing as Oprah already has an extravagant mansion on the older portion of the property, it’s highly doubtful that she will be moving into the second home. But, for me, a really persuasive countertenor will always be a kind of miracle, so the Licida of Meili Li stands out, conjuring lyricism from his great resources of agility, dynamic control and freshness of tone. That said, for easeful sheer beauty and expressive instinct, the soprano Rachel Redmond is in a class of her own in the secondary role of Aminta.

She is at home when she is embraced by the mountains, the ocean, and the trees; when night falls, she lives in a world of pure stillness, beneath a dome of stars. In these settings, she feels like her life has been set inside a painting, like she has stepped into a dream for herself. It is amazing and beautiful to me that the woman who has always loved trees has the largest private estate of sequoias in the Santa Barbara area. When I asked Oprah about her dreams of home, she talked about her childhood hopes for a place that would fully support her. She recalled the landscape around her grandmother’s house in Mississippi, the house she lived in when she was a young child, a house that was surrounded by trees, with a dirt road.

"She already has a large home in Santa Barbara — this seems to go back to something real and personal." However, the US still owes Native Hawaiians 1,300 acres across the state, according to ProPublica. As ProPublica reported in 2020, legislation to begin giving land reparations to Native Hawaiians passed in 1995, with a directive to return land seized by the US government. "I support Maui and the cause. But why are you asking us common folk who live paycheck to paycheck. We struggle to put food on table. Who helps us?" one person commented on Oprah's TikTok. In addition to being a talk show host, Winfrey is also a philanthropist, producer, author, and actress. Her endeavors include donating millions to charities, running Harpo Productions, writing several books, and starring in critically acclaimed films like The Color Purple and Selma.

Plus, it's right around the corner from the famous shopping of Madison Avenue. However, in 2012, Oprah decided to call it quits on the then-six-year-old apartment, which had prices that, at the time, started at an amazing $1.47 million. She listed hers for $7.9 million, which at first shocked fans — Oprah originally bought this pad in secret under the name of her BFF, Gayle King. Oprah's apartment had stunning ocean views and an airy, sunny ambiance. Still, it lacked a lot of the customization and upscale finishes that Oprah seems to enjoy at her other homes.