Photos Of Oprah's Secluded Island May Change Peoples’ Minds About Her

Oprah Winfrey’s made her name as a legendary media queen and a generous giver to good causes. She’s also made a packet of money, and Oprah’s splashed some of that cash on a range of homes that are quite breathtaking — including one on Maui. And though the Hawaiian estate’s based around a humble farmhouse, it isn’t quite the same as the wooden shack she spent her childhood in.

Maui’s queen

In fact, some people have dubbed her Maui’s queen. In some ways that’s appropriate, given her substantial property portfolio on the island, which covers the biggest area owned by any one person. But it’s also true that she’s a good member of the community there, so much so that the governor of Hawaii has hailed her as a friend of the islands.

Can’t buy friends

Of course, Oprah no longer has to endure the poverty that she once did. But money can’t buy you love, right? Nor can it buy you friendship. It’s doubtless hard to trust others when you know they might just be after your cash. So Oprah only has a few good pals, people whom she feels she can really trust.

Close buddies

The media star reportedly has only a few close buddies. A couple of them, Maria Shriver and Gayle King, have been part of her life for more than four decades. This is just one of the ways that Oprah’s super relatable. And like most people, finding new pals is difficult for her now that’s she’s grown.

Meeting Maria

Oprah actually met Maria in a weird way. One morning, when the former was working for WJZ-TV, she took a trip to the bathroom. There was Maria, and they started up a chat. “I forever think that that was a divine moment that happened,” Oprah told Hoda Kotb on her podcast. “Because she was one of my true, grounded friendships that carried me through my entire career.”

Partner in crime

Along with her tight circle of friends, The Color Purple star has a long-time partner, Stedman Graham. She’s been with him from the mid-1980s, though they’ve never gotten married. He’s a writer whose specialty is self-help, and he’s done pretty well at it. They were fixing up a marriage back in 1993 but didn’t get round to it, and they’ve seemingly never revisited the idea since.

Promised land

The main residence for Oprah and her partner is the Promised Land Estate in Montecito, California. When she went to a party at the property, close to Santa Barbara, she loved the place. And with her kind of money, if you love it, you get it. It didn’t come cheap, though: she had to shell out more than $50 million for the property.

Huge spread

Nowadays, the estate would set you back nine figures, but then it’s grown quite a bit since Oprah bought it. The focal point of the 70-acre spread is a sprawling mansion, measuring well over 20,000 square feet. It’s built in the neo-Georgian style and enjoys beautiful surroundings, which include fountains and flower gardens.

Beautiful place

This isn’t just any old house, either. Oprah’s spent the years since she bought it filling the property with paintings, books, and souvenirs of places and people she’s known. It’s the center of her business dealings, too. The home’s familiar to anyone who regularly visits her Instagram page, because she often puts up photos of herself there with the couple’s beloved dogs.

Dining room

Inside, the dining room’s a special feature. It’s particularly comfortable and welcoming. Originally, this area, along with the rest of the property, sported bold wallpaper and lavish vintage tables and chairs. That all went, and now the walls are more neutrally colored, while the furniture has a lot more padding!

Fine kitchen

But, of course, a dining room may be a little formal for breakfast. As you can imagine, the mansion has a fine kitchen, which remains much the same as when Oprah acquired the property. There are also a couple of home cinemas, a library, an office area, and a wine cellar. If you ever felt exhausted after walking around, you could rest in one of the six bedrooms.

Walk-in wardrobe

Oprah likes to cut a dash when she’s seen on television or at public events, so she must enjoy her wardrobe. It certainly isn’t just something that she slapped together after a trip to the mall, though. Nope, this is a whole room, featuring cabinets in the walls that house her clothes.

Lots to read

And if there are plenty of clothes, then there are even more books. Oprah just loves to read, which won’t some as a surprise to anyone who’s watched her show and seen her book recommendations. When not reading, she can enjoy a swim in the pool, stroll through the orchards, or relax by the fish pond.

Horsing around

The original property wasn’t enough for the chat star, though. She extended it by buying the estate next door, a horse ranch named Seamair Farm, in 2016. That purchase set her back nearly $30 million, and it has a low-set house created by Cliff May among its 23 acres.

Ranch house

May wasn’t just any architect, either. His specialty was the ranch house, which many suburbanites have for decades dreamt of one day owning. Oprah’s house is a fine instance of the style, covered in wood and with open, inviting spaces inside. But as her main home’s right next door, she probably doesn’t stay here.

Extra spaces

There’s more to it than just the ranch house, though. There are three other smaller dwellings, which would be just right for a guest or for employees. The estate’s well kept and perfect for horses, with plenty of stable space and paddocks. It also features its own water sources, handy given the heat of California in summertime.

Bridges buy

But Oprah didn’t stop with the ranch. When her neighbor, Jeff Bridges, decided that he wanted to move out of his Montecito estate in 2019, Oprah was there to buy it. She laid out not far shy of $7 million for the Spanish Revival house, which is right next to her own home.

Bargain purchase

This represented something of a snip, given that the estate had cost Bridges a similar amount back in 2014. So the actor wasn’t even able to get back the money he’d spent on rebuilding after a landslide had damaged the property during 2018. He’d actually hoped to get another million for the place.

Nicely renovated

Bridges had done some really nice renovation work, leaving the restrained elegance of the James Osbourne Graig design intact. It’d certainly make a nice home for Oprah if she chose to live there, offering plenty of light in the kitchen and a master suite with exposed beams and big windows that look out over a delicious yard.

Ski chalet

The chat queen doesn’t just enjoy the California sunshine, though. She also spends time in Colorado, where she maintains a ski chalet in Telluride. The modern building’s set on a 60-acre estate. She purchased it fully furnished from Bob Wall, a tech guru. The cost? It came to $14 million, a tidy bit of spare change.

Beautiful room

Oprah loves to ski, so it isn’t a surprise that she chose to snap up a chalet. And it’s pretty nice, especially the jewel in the property’s 9,000 square feet of space, namely the fabulous living room, which has a tall ceiling and walls paneled in wood. There’s plenty of light as well, with windows that go from floor to ceiling.

High tech

This isn’t just a simple alpine shack, of course! No, it’s bang up to date, not surprising given that it belonged to a techie. It has smart everything. But Oprah’s love of the old-fashioned pursuit of reading is catered for, too. There’s a library attached to the family room, as well as a retractable screen for projecting films.

Wine mine

The gourmet kitchen has gleaming countertops in stainless steel and cabinets fashioned from wood. There’s more steel in the beams, but the area hasn’t lost sight of its rustic setting, with a wall carved out of stone. And if Oprah wants a drop with dinner, she can choose something from the wine cellar, which is made to look like a mine, with an ore cart and ambient noises of leaking water.

Real rails

If the cellar impresses with its fake ore tracks, the property’s actual railway is just that bit more impressive. Yes, there’s a funicular system attached. And after a day’s skiing, relaxing in a sauna or a nice warm bath really appeals. Especially when the water stays hot, as is the case with this high-tech tub.

Island getaway

When it all gets too much for Oprah, she can take off to her estate on Orcas Island, Washington. Madroneagle lies right on the waterfront of the island, where Oprah joins other mega-rich types with luxurious homes. She didn’t get much change from $9 million for the tastefully designed house, which looks suitably rugged.

Rustic dream

The talkshow queen doesn’t even have to share her beach. Her green four-bed home has its own. Inside, it’s like a rustic dream: towering ceilings make the living room a space that needs the massive fireplace in the winter. Beams and stone walls emphasize the rural feel, while the floor contains boards salvaged from Chicago’s Sears Building.

More properties

These amazing homes aren’t even the end of Oprah’s portfolio — we’ll be looking at her Maui property shortly. And on top of that, there are some less lavish residences in Nashville and Chicago, plus a couple of vacation spots in the Caribbean. There might even be others that aren’t publicly known, too.

Hawaiian jewel

But possibly the jewel in Oprah’s property empire is her Hawaiian home. Oprah’s real-estate overlord Bob Greene mentioned purchasing land in the state to her. So he went to search for some — and found it. They had to move fast, though. Oprah recalled, “He was worried that some developer might swoop up the land and build condos.”

Land of plenty

So Oprah splashed out a bit more than $5 million for two bits of land on Maui. Along with the 23-and-change acres came a farmhouse, which was nothing special. That was back in 2003, and ever since, Oprah’s had her checkbook open, snapping up land on Maui to the value of about $60 million.

Farmer Oprah

These days, Oprah has more than 160 acres on Maui. Back in 2010 the local council even allowed Oprah to open a bed and breakfast at her estate, though we don’t know whether she ever makes the breakfast. But she definitely does have something of a farm, cultivating veggies, flowers, and fruit there.

Renovated farmhouse

The farmhouse at the center of Oprah’s estate needed renovating, so she brought in Jeff Wooley and his crew to fix it up. And when they said rebuild, they meant rebuild. They re-created the house from the studs to the roof tiles, and it now has French doors and a huge veranda.

Master bedroom

One room to be renovated was the master bedroom, which gives out onto the patio. The tall ceilings, with paintings of flowers in between the beams, make the inside of the room seem fresh and spacious. And the feeling of elegance is boosted by the vintage furniture seen throughout the property.

Veranda wraps

Perhaps the best part of the home is that veranda. It surrounds the whole house and is joined by an upper-story terrace. Lovely spots to enjoy a relaxing hour when the sun’s setting. The property makes a perfect getaway not just for Oprah but also for her family and friends. She’s even spent Christmas on the island.

Ellie hired

When it came to decorating, only one person would do once Oprah had seen a photo of designer Ellie’s Connecticut house. When the talkshow star phoned Ellie, the latter was enjoying a bath. Obviously, she took the call! And she took the job, too, once she’d talked face to face with the billionaire legend.

Quick job

In 2006 Ellie told Oprah’s website what she’d thought about the home when she got there. The design expert recalled, “I saw a small porch, a kitchen that needed work, a master bedroom that did not face the view and had a low ceiling, and no connection between inside and outside. The original plan was to do a quick job on the house then think about building the ultimate Hawaii homestead.”

Real and personal

The home decorator then explained what had appealed to Oprah about the home, adding, “She liked [the home’s] small scale. She already has a large home in Santa Barbara — this seems to go back to something real and personal. It’s a great house for her and two or three friends.”

Cozy scrapbook

Indeed, the home is very Oprah. She’s placed items in it that have been part of her existence for many years, so that it’s almost like a scrapbook. A Shaker chest adorns the reception hall, while a one-time pool-house table has been moved to the dining area. A lamp made from a tea container sits next to a couch clothed in chenille. The whole place is cozy.

Past comforts

Oprah explained on her website why she’d gone for things that were strongly reminiscent of her past. She stated, “I grew up in a rural folk environment, and I’m still rooted in things that have brought me comfort over the years.” So despite her riches and celebrity, the TV queen still hasn’t forgotten where she came from.

Community spirit

And though Oprah lives in the celebrity stratosphere, she still keeps in touch with the common folk. When wildfires struck Maui in 2020, Oprah allowed the public to use her private road after reading a plea on Twitter. This act allowed the people to get to safety and gained the TV superstar the thanks of David Ige, the state governor.

Cashmere blanket

All in all, this is genuinely somewhere Oprah can think of as home. She told her website, “I love, love, love my house. It’s a gem, so sweet and exquisite. Such a real, normal house. It feels like a nice blanket.” Not just any blanket, though, as she explained: “A lovely and soft cashmere one.”