View from above

To get a good look at the vastness of Oprah’s property, you need soak in a bird’s-eye view. If you look closely, you’ll notice a tennis court on the right side, ensuring Oprah never lacks recreational activities.  

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Modestly dubbed “The Promised Land,” the property is home to 12 magnificent Great Oak trees, which Oprah calls “the Apostles.”

First look

If you’re lucky enough to get invited to brunch at Oprah’s abode, the first thing you’ll notice is its beautiful exterior. The mansion sits on 42 acres of lush green countryside. 

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Deborah Jones via Pinterest

Would you prefer a mountain view or an ocean view? Don’t worry, you don’t need to decide, Oprah’s home plays host to both.

Have no fear of the home being dwarfed by the sheer size of the property — the mansion itself is 23,000 square feet.

Running the numbers

Oprah spent $50 million acquiring the property in 2001, and since then she’s expanded it considerably. She recently spent $28.5 million on some extra property that includes a ranch home and equestrian facility.

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That still wasn’t enough, evidently. In 2019, she acquired Jeff Bridges’ old home for $6.85 million. Oprah’s property now spreads across 70 contiguous acres in Montecito.

Take a dip

Of course there’s a pool. What celebrity-owned mansion would be complete without a spot to cool off? When Oprah and her guests want to take a dip, they do so in style.

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The pool has a nice shape and a lovely view of the shady palm trees and vegetation. We can only assume the temperature is regulated to perfection.

A leisurely stroll through the garden

Taking a walk has never been lovelier than through Oprah’s garden. Don’t you wish your backyard looked like this? There are all sorts of perfectly trimmed shrubs and trees, and breathtaking flowers.

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If this was my home, it’d be hard to get me to go anywhere outside the perimeter of my property. The garden also holds a special place in Oprah’s heart — she’s constantly posting photos of her harvests to her Instagram.

Swim with the fishes

Or maybe just watch them swim in the koi pond. Take a look at these happy fish, lazily navigating through Oprah Winfrey’s pond, not a care in the world. Clear water, plenty of food, beautiful lily pads; what more could a carp ask for?

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With 42 acres (and a few billion dollars) to work with, you might as well bring in some wildlife. Why not?

Lawn decorations that will put your pink flamingos to shame

Some people are satisfied to have a few garden gnomes watching over their backyard, but not Oprah — she’s got something else entirely. You won’t find them at Pier 1 Imports. In fact, you’re more apt to find them in an art museum.

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Chris Villaflor via Pinterest

Oprah’s yard ornaments are actually one-of-a-kind sculptures by revered Costa Rican Mexican artist, Francisco Zúñiga. The pieces depict a peasant woman in the four stages of her life. We can only imagine how this humble peasant woman feels being surrounded by such opulence.

The teahouse

No, we’re not headed toward the main home yet — first, we need to stop by the teahouse beside the garden. Reportedly, this was first intended to be a shack where Oprah and her gardeners could cut flowers.

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DIANE SMITH via Pinterest

But as it was being built, Oprah had a change of heart. Now it serves as Oprah’s home-beside-her-larger-home, complete with a gravel-lined walkway with a copper fountain smack-dab in the middle. Naturally, everything was selected by the former television host herself. Oh, wow! She’s decided to take us inside …

Inside the teahouse

Let’s take a look around, shall we? Feel free to pull up a chair, and help yourself to a cold glass of lemonade. But don’t expect to watch any television. Oprah calls her teahouse a place to “read, meditate, and enjoy a cup of tea.” Oprah’s a firm believer in meditation to hone her focus and relieve stress. 

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Cathie via Pinterest

While it seems like having more money than one could spend in a lifetime would solve all your problems, managing all those assets and running a production company responsible for several blockbuster films is hard work. Sometimes, you need to escape from it all. So while Oprah could host business meetings in the teahouse, she chooses not to.

The new addition

Because a large chunk of property with one mansion isn’t enough, Oprah recently shelled out an extra $28.5 million to acquire an auxiliary home and the property surrounding it. The 5,000-square-foot house comes with horse stables, its own swimming pool, a separate home for her caretakers, and some avocado orchards.

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Hopefully, once she’s done some remodeling, she’ll invite us back to take a look inside. But for now, let’s journey to the stables for a look around.

Stables

Oprah’s equestrian stalls have room for a dozen horses, but so far Oprah hasn’t taken advantage. She’s proven she’s passionate about dogs — at one point she even cared for 11 at once — so we’ll have to wait and see if that love will translate to caring for horses.

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Architectural Digest via Pinterest

Not that she’ll have to do any of the cleaning or training — the property contains a horse trainer’s house, so the animals can be cared for 24/7. 

Riding track

If Oprah does decide to take up the equestrian lifestyle, she couldn’t have picked a better spot. The riding ring outside the new ranch house is simply gorgeous.

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If your head’s not spinning yet, keep in mind we haven’t even entered the main home yet! Well, what are you waiting for? Come on in …

Entrance hall

Now our host has decided to let us into her main house for a peek around. Be sure to get all the mud off your shoes before you track it all through Oprah’s living room. Have a look at this lovely entrance hall, or the foyer, as Oprah likes to call it.

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Look at the ornate filigree that lines the banister and the beautiful painting that serves as the room’s centerpiece. The tables are full of framed pictures of Oprah’s loved ones. Let’s voyage in a little farther.

The library

Even if you know next to nothing about Oprah, you know she’s passionate about literature. She’s starred in film adaptations of classic novels like The Color Purple and Beloved (which her studio also produced). Getting your novel stamped with the Oprah’s Book Club logo is a surefire way to up its sales exponentially.

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Lady Rosabell via Pinterest

Therefore, it’s no surprise she has a well-organized library in her home. You can look, but don’t touch — word is, Oprah runs a tight ship and doesn’t allow guests to touch her books. However, she’s happy to recommend a good read.

The kitchen

We only get a glimpse of Oprah’s kitchen here, so it’s a bit hard to form an opinion on the decor. But wait, what’s that on the right? Looks like a pizza oven.

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Nimvo via Pinterest

Hey, you can’t expect Oprah to let all the fresh tomatoes she harvests in her garden go to waste, can you? Hopefully she’ll invite us back for dinner sometime and we can see for ourselves.

Dining room

Speaking of food, let’s join Oprah in the dining room for some nibbles. Wow! Look at that dining table — it seats up to 10 guests comfortably. We love the natural wood design and the gaudy chandeliers and candleholders.

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Alisha Moore via Pinterest

Despite the old-school, opulent design, the dining room isn’t quite as big as we’d imagined, though we suppose it’s nice to have a bit of coziness when you settle down for dinner with the family — especially in such a giant abode.

Walk-in closet the size of an apartment

Oh, my! You could easily get lost in Oprah’s closet. Look at all those shoes! It looks like she keeps everything well organized, with separate shelves for folded shirts, and the top shelves reserved for handbags.

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Sam Alvarez via Pinterest

Like practically everything in Oprah’s house, it features a chic design, conceived by the woman herself. Of course, we’re only given a glimpse, so it’s hard to imagine the sheer size of the room.

Living room

Oprah has warned us that she’s a little self-conscious about her living rooms. The smaller of the pair features coral walls and green couches and seats. There’s nothing particularly wrong with the room, though Oprah thinks it’s a bit dated and in need of a renovation.

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Daily Mail via Pinterest

There may also be a bit too much going on with the room, giving it a bit of a crowded feel. Hopefully we’ll get another look at the room once it’s been redone.

Living room 2

Oprah thinks this room is also in need of a makeover. With the plaid wallpaper and matching couch with overstuffed throw cushions, the room feels a little too ’90s for her taste.

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Cathy Kleinbart via Pinterest

In fact, by the time you’re reading this, Oprah will have sold the couch at auction — the rumor is she’s starting the bid at $3,000. Hopefully she’ll give us a look at the updated room once it’s to her liking.

Bathroom

That’s quite a bathtub! “I spend my time looking for the best possible bathtub a woman can buy,” Oprah told Vogue. There’s actually a backstory to why Oprah has such luxurious taste in bathtubs.

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Property24 via Pinterest

“It came from the fact that I was raised with my father in, like, an 1,100-square-foot house where we all shared the same tub,” she said. Having to clean the dirty bathtub left quite an impression on Oprah. “I vowed if I ever got my own place, I was going to get myself a good tub!” Similarly, she blames never being allowed to have a dog growing up for her obsession with canines.

‘The Promised Land’ at a glance

Sadly, our tour of “The Promised Land” has come to an end. Before we move on to the brand-new property Oprah purchased from Jeff Bridges, let’s get the full rundown of Oprah’s original mansion.

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Alan Light via Wikimedia Commons/CC BY 2.0

Oprah’s main home is 23,000 square feet, and contains six bedrooms, 14 bathrooms, a theater, 10 fireplaces, and a wine cellar. Quite an impressive abode if you ask us.

‘The Dude’s’ old abode

Jeff Bridges put his Montecito home up for sale in March 2019 for $8 million. Oprah, quite the accomplished real estate investor, had to have been watching the market like a hawk for six months. Her patience paid off, and she ended up scoring the Spanish revival home for $6.85 million. Though, let’s be real, what’s $1.15 million to Oprah?

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The 3,300-square-foot house will make an impressive addition to Oprah’s massive estate — it’s got three bedrooms and as many bathrooms, as well as a brick patio, pool, gardens with redwoods, orchards, and oak groves.

If Oprah keeps going, pretty soon all of Montecito will belong to her!

Oprah’s story

We hope you’ve enjoyed this tour of Oprah’s Montecito property. Now, you’re probably wondering how Oprah amassed such an impressive fortune. Here’s a condensed bio of the talk-show-host-turned-media-mogul — it’s quite an interesting story.

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Oprah came from humble beginnings. She was born on a farm in Kosciusko, Mississippi, where she would grow up under the care of her grandmother. A fast learner and gifted student, she learned to read at 2 years old, and skipped kindergarten to join the first grade. The next year she advanced to third grade.

A natural entertainer

Oprah had a knack for speaking to an audience. When she was little, she’d perform for the animals on her farm. Later, when she lived with her father in Nashville, Tennessee, she gave speeches at churches and social gatherings, and first learned she had a talent that could earn her money.

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2Sense-Los Angeles via Pinterest

But just as she was starting to settle in, she was sent to Milwaukee to live with her mother — a move that would have a devastating effect on her.

Rough times were turned around

She lived with her mother in a dangerous Milwaukee neighborhood during her young teen years, but after suffering mistreatment from men her mother trusted, Oprah was sent back to live with her father. She credits her father’s strict guidance with saving her life.

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He forced her to read religiously, and she soon renewed her passion for literature, drama, and giving speeches. She excelled in high school and then college at Tennessee State University. Oprah began working at CBS as a news anchor after turning the job down twice. At 19 years old and still a sophomore in college, Oprah became the first African American female co-anchor on Nashville’s evening news.

A career in front of the camera

When Oprah graduated, she decided to pursue her passion for reporting. This led her to Baltimore, where she took a job giving news updates during Good Morning America. She was quickly promoted to a co-hosting position on the show People Are Talking.

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In 1984, she took a big risk, moving to Chicago to host A.M. Chicago, a morning talk show that had terrible ratings. She successfully turned it around by focusing on controversial topics that invited discussion and debate. By September 1985, the show was renamed The Oprah Winfrey Show and was dominating its time slot.

‘The Color Purple’ and continued success

Oprah caught the eye of legendary music producer Quincy Jones, who wanted her to appear in Steven Spielberg’s film adaptation of Alice Walker’s powerful novel, The Color Purple. The movie was a massive success, and Oprah’s show gained even more attention and acclaim.

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Warner Bros. via IMDb

Soon after, Oprah used her advantageous bargaining position to gain ownership of the program from ABC, and started Harpo Productions (“Oprah” spelled backward). The show ran until 2011, when Oprah decided not to renew her contract with ABC.

Other mediums and investments

Oprah used her platform to launch other successful business ventures. This includes Oxygen Media, Oprah Magazine, and later the Oprah Winfrey Network (OWN), all of which have earned her considerable wealth.

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In 2018, Winfrey signed a deal with Apple to host a televised version of Oprah’s Book Club, in which she discusses books with their authors.

She’s also developed a passion for real estate (outside of the properties she keeps for herself), and has amassed quite a fortune from her investments. Clearly, she’s shown no signs of slowing down.