Inside Oprah's $100 Million Home and Her Luxury Real Estate Collection - The Gossip Geek

Inside Oprah’s $100 Million Home and Her Luxury Real Estate Collection

She’s inspiring. She’s undeniably rich. And now, she’s showing us her private residences, around the nation. Oprah Winfrey is known as a self-made woman, best known for The Oprah Winfrey Show. Nicknamed “The Queen of All Media”, millions have absorbed her practical advice and consumer recommendations. Who can forget Oprah’s favorite things audience giveaways? America fell in love, and Ms. O made billions.

Inside Oprahs 100 Million Home and Her Luxury Real Estate Collection33
Image: Coveteur

These days, Oprah has numerous media, wellness, and food ventures on her plate. The burning question is, where does this mogul relax when she’s off the clock? Despite her digital presence in American homes, far less is known about her own dwelling. As it turns out, she has many: With her main home in sunny Cali, and escapes to islands, mountains, and more, it’s intriguing to investigate her growing portfolio. Let’s take a peek at a few, shall we?

The Mansion of Her Dreams Was Just Out of Reach — Or Was It?

In 2001, Oprah was invited to a party at a special mansion in Montecito, California. It was love at first sight: She knew she had to move in and make it her own. First built in 1912, the 23,000 square foot Georgian-style house had frequent renovations over the decades. It just got better, and better. With private views of the ocean, it had an ideal location, too.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection2
Image: Oprah Daily

As she toured the property, she found more and more hidden gems that confirmed this had to be her future West Coast headquarters. The catch? It was not for sale. Oprah quickly got to work making generous offers on the property. Eventually, the savvy businesswoman made a pitch no one could refuse.

She Got the Deal Done for $52 Million, Because She’s Oprah

We all know if Oprah really wants something, she’s going to get it. The offer was $52 million. When the dotted line was signed, it represented one of the biggest sales of a house in U.S. history. During the course of her Chicago-based show, Oprah lived in a sky-high penthouse above the snow. As a woman who has owned more than 20 dogs, she knew that apartments were problematic. It was time for a bigger yard!

Inside Oprahs 100 Million Home and Her Luxury Real Estate Collection35
Image: O, The Oprah Magazine

According to Oprah: “I will forever believe that buying a home is a great investment. Why? Because you can’t live in a stock certificate. You can’t live in a mutual fund.” Experts say that Oprah would get close to $100 million today if she were to sell. That’s because she did her own revamping and added major attractions. She named it “The Promised Land”. Soon, we will see how fitting that nickname really is.

The Rosy Grounds Are Not Exactly Garden Variety

What can $52 million fetch these days? To start, check out the gardens. When Oprah first saw the property, it reminded her of Gone With The Wind. One could even compare the well-manicured flowers and arches to a royal property. It’s the perfect place to conduct big interviews, and that’s exactly what has been happening lately: Viewers may recognize it from the Harry and Meghan chat that rocked Buckingham Palace!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection20
Image: Veranda (top) USA Today (right)

A friend helped Oprah name the garden estate to celebrate her path from rags to riches. It was positively biblical, invoking a reference of slaves reaching paradise. Given her family history in the United States, The Promised Land was downright symbolic. Her enslaved ancestors would be shocked, and she wanted to honor this journey. What was inside the place?

Luxe Yet Folk, Oprah’s Décor Reflects Her Soul

With 14 bathrooms and 6 bedrooms, there were plenty of rooms for work, play, and everything in between. There’s a private theater and wine cellar inside, and 10 fireplaces to be cozy all year round. How did she approach decorating such a gigantic project, though?

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection15
Image: O, The Oprah Magazine (top) Oprah Daily (bottom)

Her philosophy is simple. She shared: “I grew up in a rural folk environment, and I’m still rooted in things that have brought me comfort over the years.” Muted orange and green make a statement in this example, with floral patterns and antique styles for decor. Classic gold pieces provide a contrast throughout the space, too. Even the guest rooms in this mansion have been designed with intention. But is The Promised Land a place to really live and relax?

As It Turns Out, Comfort and Class Are Compatible

According to Oprah, “you’ve got to make sure the exterior of your life reflects what you’re feeling on the inside.” Over the years, she had tried to make this her approach to life in general. Then, she realized her house had to be a part of that, too! Her original design was changed, as she gathered wisdom.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection29
Image: O, The Oprah Magazine

She shared: “It was the place I thought you should have when you start earning money and can finally afford some pretty things. So you buy a silk sofa, but suddenly you can’t let your dogs up on that sofa. And it wasn’t just the dogs…My butt kept sliding off those silk cushions! I live in my true comfort zone now.” What else makes Oprah comfortable in this shabby chic palace?

The Book Club of Her Dreams Certainly Came True

Oprah once shared: “Nothing, not one thing or activity, can replace the experience of a good read — being transported to a different land, a different realm, through words and language.” For this level of passion, she needed an exquisite reading room. Longtime fans of her book club will be tickled to see where she pages through all that inspiration and wisdom. It’s all right here, among these orderly shelves.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection10
Image: O, The Oprah Magazine (top) Instagram / Oprah (bottom)

Observers may notice one deliberately chosen piece among the books: The large doll that lives on the sofa. Oprah has talked about her childhood and a real lack of toys with her skin color in the old days. Unsurprisingly, she chose meaningful decor as soon as she had the chance. And it’s adorable!

A Closet Fit For a Queen Was an Obvious Requirement

One more thing everyone knows is that Oprah has quite the wardrobe. She once estimated she owned as many shoes as Jackie O, and doesn’t bother to keep track. There’s got to be a place where she keeps it all, right? At The Promised Land, there is more than enough space to store her designer threads.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection4
Image: Essence (left) Hyperion (right)

Her strategy was simple when she created her giant closet systems. She explained: “I want to create a space that gives me access to the stuff that helps me, to things that hold a place of meaning for me. Because if you can’t do that, then you’re not using your things — your things are using you.” Smart, but that’s no surprise!

A Toast To The Host, Oprah Has Dining Space to Spare

East of Santa Barbara and near the Santa Ynez Mountains, Oprah chose to buy in one of the richest towns in the United States. Montecito homes start at $1 million, but an $85 million asking price isn’t impossible there. Plenty of celebs wander around the neighborhood. Oprah has a famous and fascinating guest list that she invites to dinner. And invite, she does!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection9
Image: Daily Mail

She and longtime partner Stedman Graham never had children of their own. Oprah has one sister, who has four kids. Her family is pretty small, and she loves to have them over. They also show love through food for other special people in their lives: Oprah has a school for girls in Africa, and the students have flown by for a meal, too. They call her beau Uncle Steadman!

She’s Got a Giant Jade Tub, Since Baths Are a Serious Hobby

When Oprah was a child, she had a small, stained tub she had to scrub as a chore. As a legit rich lady, that’s never going to happen again. And fans have heard her speak about bathing as a major hobby for years. She explains: “I have a bath every single day of my life. And if I can have two or three — amazing. Nothing terrible is going to happen in the bath, so I always find time for that.”

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection1
Image: Instagram / Oprah (left) Luca Trovato (right)

For a serious interest, Oprah is willing to invest. In this case, that means she got a tub made out of a giant chunk of green onyx. In other bathrooms, she has more options. Right now, she is really enjoying another vessel custom carved to the shape of her unique body. What does she do to relax, out of the water?

Oprah’s Teahouse is a Must For Any Heart-To-Heart Chat

It was important for Oprah to designate at least one area a tech-free zone. That would be the tea room, nestled deep in the rosebushes, dahlias, and hydrangeas of the gardens. The room was once used for workers, but she thought it would make a great place to lounge and read so she renovated it into what it is today.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection22
Image: O, The Oprah Magazine (top) Forbes (bottom)

The tea house has been the site of some interesting interviews, like Howard Schultz, the CEO of Starbucks. But usually, she uses the venue for some old-fashioned me-time. She explains: “It’s my dream, having a place like this. Some people ask, ‘Why do you need more space?’ And I tell them, ‘I need it to restore myself.'”

Horsing Around, With An Equestrian Estate

Even though Oprah Winfrey has plenty of real estate in her initial purchase, she soon learned that the farm next door was for sale. Quickly, she snatched it up. For an extra $30 million, she now owned a private horse experience, complete with stables! The Promised Land was rapidly growing.

Inside Oprahs 100 Million Home and Her Luxury Real Estate Collection30
Image: Variety (left) O, The Oprah Magazine (right)

The 23-acre estate had covered stalls and spacious pens. Riding and exercise areas showed off the Pacific Ocean and the nearby mountains. It was surrounded by a private avocado grove. And it came with an extra house, whether she needed it or not. 5,000 square feet meant four extra bedrooms, four extra fireplaces, and a pool. What’s her drink of choice, in between these outdoor dips?

Chilling at the Pool Is a No-Brainer, All Year Round in Cali

Oprah was born to a single mom in the Jim Crow South, and never knew anything close to the good life. Now, it’s incredibly easy for her to lounge by the pool with a Moscow Mule. The combo of vodka, lime juice, and spicy ginger beer really hits the spot in the sunshine. It’s her favorite!

Inside Oprahs 100 Million Home and Her Luxury Real Estate Collection36
Image: Daily Mail

According to O: “Your home should be your sanctuary, the thing that rises up to meet you.” At The Promised Land, her amazing American journey is really put into perspective. But don’t think Oprah was satisfied with this absolutely luxurious hideaway. This was just the beginning of her adventures in real estate. Where else does she like to sleep, occasionally?

Next, She Needed a Tropical Hawaiian Escape

California was lovely, and she would never deny that. But it’s only semi-tropical. So Oprah decided she needed a full-blown island retreat to get away from the mainland. Her property manager had scouted out land on Maui for a long time, and he found the perfect chunk for Oprah to purchase. It was conveniently undeveloped, without condos cluttering the view. Luaus, pineapple drinks, and girls’ nights with BFF Gayle King were sure to become a frequent occurrence.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection12
Image: Instagram / Oprah (top) Hawaii Real Estate (bottom)

Maui in particular is covered in lush nature: Bamboo forests, gorgeous sand, and exotic waterfalls mean that Oprah has real paradise whenever she decides to escape. Some may have heard that the island is actually in between two big volcanoes. But don’t worry, they are dormant.

She Bought A Volcanic Plantation, And A Mansion

The 163-acre property already hosted a lovely house, but it needed work. That was nothing new at all for Oprah and her design team. They love a challenge! She changed the home floor plan most of all. They tore walls down to make many of the rooms more open, and the master bedroom got a higher ceiling. They also installed a lovely wraparound porch to cover the entire home. Now, Oprah has 360-degree views of Hawaii and all its splendor.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection5
Image: MSNBC (left) Oprah Daily (right)

The house is just a part of a farm on the outside of one volcano. It’s special because of the volcanic soil and sits at 40,000 feet above sea level. Although Hawaii has to import 90% of its agriculture, Oprah is actually self-sufficient here. She has chickens roaming around for fresh eggs every day. And she has more than 100 fruit, veggie, and herb varieties right in her backyard!

Far Away From It All, Oprah Has Become An Organic Farmer

What precisely does she grow on that rich, rich soil? All the staples are complemented by gourmet varieties, like baboon-butt radishes, black prince tomatoes, and radicchios. Oprah does compost and tries to be environmentally friendly, with top tips from a plant guru. For a woman that spoke about her struggles with healthy eating for decades in front of America, she can’t get enough of these freshly grown salads. It’s no compromise!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection11
Image: Glamour (left) The Best Publishing Company (right)

Plus, getting in the dirt once in a while is a nice break for this wealthy, down-to-earth woman. Oprah revealed: “I can get excited over little things. I see a basket of heirloom tomatoes from my garden, and it’s so beautiful that I have to take a picture. Just the bounty of it, the fact that this just came out of the ground, the fact—oh, I can go on and on about the tomatoes until people say, ‘Hey, it’s a tomato!'” But the question is, does she share?

Farm-Fresh Tropical Dinner Parties, Please

It’s all very far away. But as it turns out, a lot of known names live nearby, at least part-time. Cher, Julia Roberts, Will Smith, Drew Barrymore, and Clint Eastwood actually have properties on the Hawaiian islands. Just imagine the breezy dinner parties with these A-listers!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection23
Image: Entertainment Tonight (top) O, The Oprah Magazine (bottom)

Oprah’s “Favorite Things list” always included great home decor ideas. Here, lovely plants and candles make this bright dining space perfect for Maui dinners with guests. There are enough sleeping rooms here for locals to extend a comfortable visit, too. But fans wonder most of all: Where does Oprah sleep?

Beach Bed Vibes Make This a Place to Stay, and Lay

Check out this gorgeous bright bed sanctuary. From a room adorned with white linens, Oprah can directly walk onto a terrace. The high ceiling makes this airy, open master bedroom incredibly elegant. Ocean views, Pacific winds, and a Hawaiian sunrise? Yes, please, said O.

Inside Oprahs 100 Million Home and Her Luxury Real Estate Collection31
Image: InCollect

Never shall she stay in a luxury hotel, in the 50th state. Oprah shared: “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. A lovely and soft cashmere one.” Looking at the picture collections released online, it’s hard to disagree!

That Porch Really Has More Meaning Than It May Seem to Outsiders

In the south, Oprah had lived with her grandmother. But when granny died, young O was sent to live with her mother in Milwaukee. In her writing, she has revealed that these times were especially rough. What was her first night like, in that new house?

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection3
Image: Michel Arnaud (top) O, The Oprah Magazine (bottom)

Oprah revealed: “The night I arrived in Milwaukee, the woman my mother was boarding with, Ms. Miller, took one look at me and said, ‘She’ll have to sleep on the porch.’ My mother said, ‘All right.’ As I watched my mother close the house door to go to the bed where I thought I’d sleep, I was consumed with a terrified sense of loneliness that brought me to tears.” These days, she can create new meaning with her luxury porch — and she can finally relax, body and soul.

Relaxing With The Boss is Easy Breezy, and Never Freezey

Oprah has a well-known penchant for pedicures and has kept a personal specialist on call for more than ten years. It’s one of her favorite ways to take care of herself. In addition, she has other paid staff serving in dietary and training roles. Naturally, that might mean travel for such employees. Surely they don’t mind, given this location!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection17
Image: Instagram / Oprah

For guests that get sick of her one-of-a-kind Hawaiian home, there is an escape. Oprah also has a private paved road that goes right to the best shopping on the island. Easy access is the best kind of access, and Oprah wasn’t going to invest so far away just to be inconvenienced. It’s paradise, through and through. But just in case things do get too sweaty, this billionairess has made sure to buy colder retreats, too. What’s one example?

Now, This High Tech Cabin in the Trees

When it’s time for a winter break, Oprah’s got that setup. It’s all right here, in the mountains of Telluride, Colorado. The extraordinary property has to be seen to be believed, and cost her a cool $14 million. The luxury mountain escape is perfect for skiing and snuggling with Stedman!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection8
Image: Joshua Johnson Photography

With five bedrooms on 3.25 acres, the 8,700-square foot house is very modern, and that’s how she likes it. A heated driveway that keeps snow away and a mobile phone plant watering system make upkeep easy when she is out of town. Cameras monitor everything to provide privacy and serenity deep in the woods. Don’t even try to sneak around, fans!

Treetop Views, an Enchanted Bridge, and a Firepit

Winding through the trees around her house is a unique, color-changing glass bridge that cost her around $140,000. It’s connected to an observation deck 35 feet in the air with a gas-powered, black lava rock firepit. In the middle of a Colorado winter, this is a delightful way to warm up. And far above any local bears!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection16
Image: Joshua Johnson Photography (top) Zillow (bottom)

Inside, the views are just as spectacular. This luxurious room on the top floor has massive windows, as does the rest of the home. Gorgeous wood is an ideal contrast with the woodland world outside. It’s a very comfortable way to experience nature without all the bugs and poison ivy. Where else is there a great view in this treehouse?

Relax in the Hot Tub Surrounded by Forest Canopy

Sure, Oprah has plenty of impressive bathtubs in all of her properties. It’s a stated priority, from the woman herself. But in this home, there is also a hot tub for relaxation. Whenever she gets in the mood, she can swirl her stress away surrounded by glass, high in the treetops. The glass even opens if she’s feeling a little adventurous.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection18
Image: Joshua Johnson Photography

Plus, she can use a sauna before or after the tub. Hot rooms may sound like torture to some, but others soak it up. Oprah notably had Dr. Oz on her show talking about the health benefits of such installations, namely a new infra-red version on the market. Could that be what she has here?

Artistic Novelties Pull Together Each Majestic Room

With no shortage of mountain views, some might assume guests are just staring out of the window all the time. But Oprah made sure that the interior is a visual delight, too. The beauty of this property cannot be entirely credited to the current owner. Ms. O bought the home from a serious African art collector. There was just no need to change the theme!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection28
Image: Joshua Johnson Photography

Oprah was delighted to inherit some truly unique paintings and sculptures. She loves Africa to begin with, so the aesthetic was definitely a cherry on top of the super modern cabin. But fans know there is one thing she doesn’t want, but rather needs A real kitchen. How was that space, here?

Oprah Just Loved This Cozy, Wood-Paneled Kitchen

Not too shabby, really. The cooking space in this home is spacious, making it a great place to do food prep with visiting friends. Stainless steel was chosen as the main material here, a trend in contemporary design. No heavy chemicals are needed to clean it, and it’s recyclable. Fitting for the forest vibe, thought Oprah.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection13
Image: Instagram / Oprah (top) Joshua Johnson Photography (bottom)

If guests tire of Oprah’s soup recipes, it’s easy to get out and visit nearby Telluride for award-winning cuisine. The fancy mountain town is a great backyard, which only adds to the value of this venture. As a bonus, Oprah has a $240,000 private tram directly to the ski slopes in just one minute. No joke, it’s easy as 1, 2, 3!

She Also Has This Estate in Washington, Close to Canada

Another day, another property. Oprah must have realized that Washington State was underrated. She decided to get to know the northwest a bit more and purchased a gigantic home in between Seattle and Vancouver. The area is called Orcas Island, and it is the biggest of the San Juan Islands. Nowadays, the area is becoming a known hotspot for eco-tourism. Who knew?

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection7
Image: Wally Gudgell

Like many of her properties, this purchase has a name: Madroneagle. She bought it for $8.275 million, which is chump change for a woman worth $2.7 billion. This Washinton wonder sits on 43 acres with several structures. The main house is 7,303 square feet, but there is a craft shed, a tea house, a gazebo, a barn, and a guesthouse, too! Let’s take a deep dive, right now.

She’s Meeting the Locals, Little By Little

Although she has never spent much time in the area, Oprah is making connections now. In nearby Seattle, she held an inspiration weekend seminar with OWN Network personality Iyanla Vanzant. For now, she doesn’t live in Orcas Island. But it might be interesting in the future if she ever has serious business there.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection24
Image: Windermere Real Estate (top) O, The Oprah Magazine (bottom)

The region is gorgeous, no doubt. It’s a great green place to explore with her dogs and enjoy breathtaking views of the pacific. When she comes home, she can relax on the charming patio with tea and a book. Retiring for the evening inside Madroneagle only gets more exciting, from there.

Northwest Luxury Means Wood, Wood, Wood

Surprise: It’s 7,303 square feet. And entering the home, it is shocking how high the ceilings really are. It’s hard to miss the wooden beams that decorate the scene, almost like a luxury cabin. The wooden floor happens to be old wood imported from the Sears building in Chicago, for a little nostalgia. Nice, Oprah!

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection14
Image: Windermere Real Estate

The grand living room connects to the dining room and kitchen. Many more species of wood were used throughout the room, including from old factories in Seattle. There is a wood-fired pizza oven, too. The theme is clear in terms of material. For an authentic finish, there is art from local indigenous tribes of the northwest. Four bedrooms and five-bathroom mean plenty of room for Oprah, Steadman, and even best bud Gayle King to stay and play. Will they, soon?

Visitors Can Enjoy Private Space, of Course

Oprah has recounted how she decorated her first apartment when became wealthy. She explained: “My Chicago apartment was done in cool white with an aubergine bedroom that in my fantasy felt sort of womblike but in reality was pretty tomblike, even on sunny days. Still, everything was glossy and chic, slick and sleek—exactly the place I thought a successful TV personality was supposed to have.” In none of her recent homes has that trend continued?

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection6
Image: Windermere Real Estate

Here, Oprah chose a shabby chic guest bedroom design. It’s unlikely Gayle or anyone else will find the aesthetic intimidating. It’s downright cozy, and an escape of sorts from snobbery in the industry. It has a logic to it, no doubt, for anyone questioning the decor. Madroneagle, for the win!

Oprah Made Leisure the Name of the Game

No luxury estate would complete without a gym, a woodworking shop, and a yoga studio. Or at least, that’s what Oprah thought when she made sure that Madroneagle had all these amenities and more. A pond, an Asian garden, and yet another tea house are here, too. And because of her well-known weakness for books, she installed an extensive library, just waiting for readers.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection27
Image: Windermere Real Estate

That last part? Not a small thing. She shared: “Books were my pass to personal freedom. I learned to read at age three, and soon discovered there was a whole world to conquer that went beyond our farm in Mississippi.” Clearly, she has come a long way. Oprah has a presence all around the nation, with mansions to boot. It’s hard to pick a favorite from this collection, isn’t it?

Fancy Fisher Island is a Millionaire’s Club, And She Craved Property There

It was only natural that Oprah would scout a piece of the Florida pie. But with so many beautiful beaches in The Sunshine State, where would she settle? The answer is a luxury one, just off the tip of South Beach on a manmade island. Normies can’t pop by. This retreat is only accessible by ferry, helicopter, yacht, or seaplane.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection44
Image: O, The Oprah Magazine (top) CNBC (bottom)

Once the private winter resort of the Vanderbilts, their mansion and villas remain. But for decades, this 216-acre island been built into an enclave of costly condos and homes for the ultra-rich. It’s quite the community: Ricky Martin, Julia Roberts, Mel Brooks, Andre Agassi and other big names have all had spots here at one time or another livin’ la vida loca.

The Specs Are As Fancy As One Might Expect ‘Round These Parts

For O, sea views were key. The 6,170-square-foot residence she chose has direct ocean views through sliding glass walls. Four bedrooms and six bathrooms offer plenty of space for guests to enjoy plush waterfront scenery. The layout is delightful, complete with 20-foot arched ceilings.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection42
Image: Insider

Hardwood and marble floors and light wood furniture are a big theme in the airy living room. It’s tropical elegance, a marked difference in design than some of her shabby chic projects. But when you’re Oprah, there’s no need to choose. Buy them all, she said: Then, she did.

It’s Small Compared To Some of Her Homes, But the Appeal is Exclusivity

To make it more obvious why Oprah felt at home here, Fisher Island was named the richest U.S. community by Forbes in 2011. It is sometimes billed simply as the richest zip code in America. And that, friends, is exactly where Oprah Winfrey belongs.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection41
Image: Facebook / Fisher Island Club & Resort (top) Insider (bottom)

The privileged who live there have an average net worth of more than $57 million. 722 residents hail from more than 40 countries, though only 1/3 live there full time. When they do, they enjoy a 24-hour marine patrol and a security force of fifty to make sure the riff-raff stay away. Oprah could theoretically host dinner parties with just about any head of state there, in peace and quiet.

There’s Bright and Breezy Island Vibes in This Florida Compound

Oprah’s longtime designer Nate Berkus once advised: “In a small space, you want to keep the bedding as simple as possible so it looks clean, calm and collected.” Here, there was no need. But she still loves to cozy up in white linens, from time to time. Who doesn’t?

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection46
Image: Insider

It’s also got a whole lot of white and beige, with Tommy Bahama aesthetics. The rattan hanging art and clean, light sofas create a contrast: Distressed and neat, all in one. It’s neutral and beachy. And it’s a great setting to recharge, while gazing at the sea.

She Heard Rest is the Best On Fisher Island, And That Was Right

Living part-time or full-time on this island is not an easy leap. Anyone hoping to become a part of the community must join the Fisher Island Club. This involves dues — serious dues. First, there is a one-time $250,000 fee. Then, every year, there is another $22,256 bill just to own there. It may sound pricey. But honestly, not for O.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection43
Image: Facebook / Fisher Island Club & Resort (top) Insider (bottom)

So what does Oprah access, when she’s not pursuing her famous bath hobby? Members of the club visit high-class restaurants, a golf course, a spa, a beach club, and private beaches with better sand shipped in from the Bahamas. There are deep-water marinas for yacht docking and tennis courts for playtime. Something for everyone, in a way.

The Home Has All The Right Amenities For Work And Rejuvenation

Back at home, the island condo has a nice setup for Oprah to stay in. There’s a fireplace and bar for evenings with Steadman. There are cozy rooms with leather upholstered walls and a large terrace for sea tea. And when O wants to get a wee bit of work or workout done, there is an office and gym.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection45
Image: Insider (top and bottom)

Overall, this sounds like a dream. One might think that it would be part of her permanent collection. But surprisingly, she sold it: For a mere $13.5 million, Canadian billionaire Lawrence Stroll took over. And he only kept it for six years, selling it for $20 million to another buyer later on. Perhaps Fisher Island is a temporary curiosity, for many!

Oprah’s Collection Needed a Luxe NYC Penthouse, High in the Sky

Sometimes, a gal just needs to visit the city. New York City, specifically. And even though Oprah was a longtime, loyal Chicago resident, she does have an appreciation for its bigger cousin on the coast. No one was surprised to learn that NYC was a target for her portfolio. How could it not be?

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection38
Image: Essence (left) Christie’s International Real Estate (right)

It was called Place 57, and it was a sleek, new tower in Midtown Manhattan. Her buy was a 2,530 square feet, 3-bedroom, 3.5-bathroom penthouse with glass to spare. It has 12-foot high ceilings and walnut floors inside. Allegedly, best bud Gayle King ended up living there for a while. For a mere $7.1 million, that’s a favor Oprah had the power to do.

It’s Classy With Tasteful Hardwood and Windows To The Ceiling

Located on the 36th floor, 2,530 square feet of glass hugs every rooms. There is plenty of indoor space in a city that lacks exactly that. And Oprah made sure there was no shortage of outdoor space, either, with a 750 square foot wrap-around terrace.

Inside Oprahs 100 Million Home and Her Luxury Real Estate Collection47
Image: The Corcoran Group (top and bottom)

No city view can go unnoticed, in this rare residence. An exquisite birds-eye view shows everything from the George Washington Bridge to Central Park. It’s a glimmering sight of the city that never sleeps. But what about the nitty-gritty needs of daily living?

There Is A Large Kitchen For All Her Manhattan Dinner Party Needs

Unlike her organic, volcanic plantation in Hawaii, not a lot of food naturally grows in the city. No matter: Oprah always has access to the best of the best, delicious deliveries. In this large, spacious kitchen, everything is state-of-the-art for culinary experimentation.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection37
Image: The Corcoran Group (top and bottom)

White oak cabinets and dark countertops are the theme in this one. There’s a center island for food prep, and a wood-burning oven. But if it truly was Gayle living here with Oprah’s blessing, it probably wasn’t used much. Allegedly, Oprah’s BFF doesn’t know how to cook. Gayle opts for PB&J when she’s home alone!

Unlike Most Residents, Oprah is Always Cozy In The Big Apple

Behind the kitchen, a corridor leads to a water and dryer, three walk-in closets, and a master suite. There’s a jetted tub and a separate shower for refreshment. And the building itself always has someone on call to make sure comfort is a high priority.

Inside Oprah s 100 Million Home and Her Luxury Real Estate Collection40
Image: Apple TV (top) The Corcoran Group (bottom)

Tower residents enjoy personalized services like a 24-7 doorman and concierge. There’s a fitness center, children’s playrooms, conference rooms, and a french crystal garden. All up to the highest luxury standards, of course. For any property in Oprah Winfrey’s name, no one would expect anything less. Live your best life was her slogan!