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Oprah’s Secret $88 Million Home Tour



Oprah Winfrey is known around the world as one of the most successful self-made women of all time! Despite her very public presence in each and every one of our homes, little is known about her dwelling. As it turns out, she has several!


While her studios were located in Chicago for decades, her main residence is currently in South California with the tiny, modest price tag of only $88 million. As a private person, it is rare for her to let us in — but information has accumulated over the years to give us a glimpse of her various mansions! Let’s take a look at a few, shall we?

From Rags to Riches

Best known for “The Oprah Winfrey Show” and named “The Queen of All Media”, millions of American women related to her unique mix of emotionally honest communication and practical advice. And who can forget Oprah’s favorite things or the lavish holiday giveaways to her audience? America fell in love, and fell hard.


Oprah was the first African-American billionaire in North America, but she actually also holds the title of being the richest African American man or woman of the 20th century — period! We are impressed. The burning question is: Where does a one-of-a-kind, high-powered billionaire businesswoman relax when she’s off the clock?


California Dreaming

Oprah’s main mansion is located in one of the richest towns in the United States: Montecito. The community is located east of Santa Barbara in Southern California, near the beaches of the Pacific and the Santa Ynez Mountains. Absolutely gorgeous, and a relaxing retreat from the bustling city life of Chicago for sure!

Conde Nast Traveler

Listings in Montecito generally start at $1 million, but $85 million is not unheard of! It’s also not unusual to find a celebrity on the street in these exclusive neighborhoods, and Oprah must feel right at home.

Bye Bye City Life

Before the sunny days in California, Oprah took up residence in a sky-high luxury condo in the center of Chicago at the famous Water Tower Place. Super convenient for access to Harpo Studios everyday. By the way, have you realized that ‘Harpo’ is simply ‘Oprah’ spelled backwards? Of course it is!

But a condo in the sky is no place for dogs, and Oprah certainly is a dog lover. She currently has five, and we can see why there was a need to find a bigger yard! In 2001, Oprah was invited to a party at the mansion she now calls “The Promised Land”. She knew she had to have it for herself! But sadly, it was not for sale.


The Mansion

Naturally, the savvy businesswoman made an offer the owners couldn’t refuse: $52 million! Historically, this was one of the biggest sales of a home in the United States. But why? What was so special about this property, with so many mansions for sale on the open market?


Originally built in 1912, renovations on the Georgian style house have frequently taken place over the decades to suit the tastes of different owners. Overall, the estate is around 23,000 square feet and features private views of the ocean. While she may have paid merely $52 million, the value has increased tremendously. If Oprah were to sell it today, she would make more than a few extra dollars. It is currently evaluated at $88 million, nearly $30 million more in less than 20 years!

Garden Living

So what can $52 million buy you these days? It turns out that this purchase included 14 bathrooms and 6 bedrooms, along with a variety of other rooms for work and relaxation. But just in case Oprah gets chilly during the extremely mild winter season of Southern California, she also has 10 fireplaces to choose from.


The magical gardens outside are complemented by the private theater and wine cellar inside. When she first saw the property, she said it reminded her of “Gone With The Wind”.


Reaching the Promised Land

A friend helped Oprah rename the property to symbolize her journey from rags to riches. “The Promised Land” invoked biblical reference for an African American living in paradise in the modern age whose ancestors were slaves, just like the Bible.

Sage Auctions

Oprah was actually born to a single mother in the Jim Crow-era South, and she wasn’t able to wear new clothing or enjoy anything close to the good life. Now lounging by the pool with a Moscow Mule (her favorite!), she can reflect on her own amazing American journey with a lot of perspective.

Welcome Home

The main entrance is an area that Oprah refers to as her “foyer”. Designed banisters on the staircase frame an area filled with pictures of those she loves so she can see them greet her when she gets back from a hard day’s work.


While some celebrity homes might appear to be cold and sterile fashion statements, Oprah clearly wanted a personal touch and deeper meaning. Style over substance was never going to happen, and we are not surprised.

The Reading Room

Longtime fans of Oprah’s Bookclub will be excited to see where she gets down to business finding all that inspiration and wisdom. Right here, in the reading room! Observers may notice the large doll permanently set on the sofa. Oprah has talked about her disappointment that dolls during her childhood did not reflect her skin color, and there is sure to be personal meaning in this unique and deliberately chosen decoration.

Observers may also notice how orderly her shelves are. Maybe no one is surprised that a self-made billionaire is disciplined outside of the office as well!


Bubble Time

Oprah remembered the small, stained tub her family used to have growing up, which was actually her chore to scrub. She knew she wanted luxury in this room, because bathing is her hobby! She loves to enhance the experience with new and exciting finds, much of which she included on “The O List” to share with her readers.

Luca Trovato

Oprah believes a good bath can soothe the body and soul, and she has replaced her tubs from time to time to keep things exciting. She used to have this hand carved tub made of a giant single chunk of onyx! Following her own advice, she replaced it during a decluttering and organizing process some time ago. Currently, her upgraded tub is specially molded to the shape of her body!

Home Sweet Home

Every room boasts its own style in Oprah’s house, and the guest rooms certainly have not been ignored. Purple makes a statement in this example, with floral motifs and glass lanterns fitting the theme. Classic gold pieces provide a stylistic contrast with the prints throughout the space.

Like many rooms, this one has a fireplace to keep cozy when one is away from home. Her special touch includes fresh flowers to make the experience even more luxurious for those who get invited to stay at The Promised Land.


Care for a Cup?

In the garden area is a lovely tea room for heart-to-heart chats. We imagine best friend Gale King has been over for a cup or two! The room was historically used for workers to do gardening tasks, but it turns out there is more than one way to use a space — and Oprah has done it with style.


Despite being the unchallenged queen of afternoon TV, the one thing missing in this serene room is — you guessed it — a television! Everyone needs a little peace and quiet sometimes, and it is clear that Oprah had this in mind when designating the space as a technology-free zone.

Female Figures

While Oprah has some classical statues throughout her extensive gardens, there is a rather unique piece that she bought molded in pure bronze. This sculpture is called ‘Grupo de cuatro mujeres de pie,’ and was made by an artist in Mexico named Francisco Zúñiga.

Inspirational Artworks

As a champion of women, we see why she liked the theme of this piece. Women are shown at each stage of life, from the teen years through pregnancy to grandmotherhood. How much did this artistic garden inspiration cost her? Merely $3.1 million dollars, a small purchase for a multi-billionaire at a Tuesday auction. No big deal.


Part 2: The Farm

Oprah was close with her neighbors, but unfortunately one of them died in recent years. She decided to purchase next door Seamair Farm from the grieving family, doubling her estate. It just grows and grows!

Architectural Digest

How much did this farm cost her? Why, only $28.9 million! While a farm might sound like a place for veggies and chickens, it turns out that fancy horse riding is now also part of Oprah’s ultimate California hideaway. The property includes stables and a beautifully done riding course for equestrian enthusiasts! An additional house is maintained on the farm, just in case she wants to get away from her Georgian mansion. And when she is not riding horses with friends, she can take them for a stroll through her avocado and fruit groves, stopping at a gorgeous koi pond for relaxation!

An Island Getaway

If you thought that Oprah had enough real estate, you would be wrong. California was just the beginning! Oprah decided she needed and island retreat to get away from the mainland, and she found just the place!

Michel Arnaud

Bob Greene is one renaissance man in Oprah’s life, working as both her personal trainer and property manager. After scouting the islands for more than a decade, he knew exactly the beautiful area that would really wow her. This undeveloped area was just perfect, and he knew it would be better if she bought it right away before it got covered with condos!


Aloha, Maui!

Hawaii is actually a grouping of eight islands, and Bob knew that Maui would be perfect because of its lush nature. Bamboo forests, exotic waterfalls, and gorgeous sand means that Oprah has access to real paradise whenever she wants! Maui is popular for luxury honeymoons and golfers who want to try brand new courses in the tropics.

Hawaii Real Estate

Fun fact: Maui is actually in between two giant volcanoes, but don’t worry — they are dormant! In the Hawaiian language, they are called “house of the sun” and “house of the moon”. The east volcano is actually the largest inactive volcano on earth!

Renovating for Style

Oprah chose a lovely house in Maui, but it needed work. Nothing new for Oprah and her team! Designer Jeff Wooley was hired to change the home floor plan, and major additions were made to the inside and outside of the structure.

Michel Arnaud

The rooms themselves were made more open and welcoming by tearing walls down, and the master bedroom was given a higher ceiling. A staircase was moved to make the most of the space, and this porch was changed to wrap around the entire exterior. Perfect for breezy relaxation and 360 degree views of gorgeous nature!


Dinner Parties in Paradise

Oprah’s “Favorite Things list” always included lovely plants and candles for beauty and ambience in the home. It is clear she takes this seriously! This bright dining space is perfect for Hawaiian dinners with special guests. But who exactly can pop by for a meal all the way in the Pacific Ocean?

Michel Arnaud

It turns out that a lot of familiar faces actually live nearby, at least for part of the year! Clint Eastwood, Cher, and Julia Roberts have properties on the islands. Will Smith and Drew Barrymore do, too. Just imagine the dinner parties with these Hollywood A-listers!

The Tropical Farm

If you thought Oprah’s California farm was impressive, take a look at her Hawaiian project! At 40,000 feet, this farm is just on the side of the large island volcano. What does she grow there on that rich soil? All the usual basic vegetables are complemented by some really gourmet varieties. Have you ever heard of baboon-butt radishes? Black prince tomatoes? What exactly is a ‘radicchio’, anyway?

Chris Craymer

Besides the plants, Oprah keeps chickens on hand to make sure she always has the freshest eggs. Hawaii actually imports almost 90% of its agriculture, but Oprah has more than 100 plant varieties of her very own as a self-sufficient farmer!


Compost Guru

Trainer Bob Greene also had some unique knowledge about the nutritional end of things, including the process of growing food! To keep Oprah’s farm in tip top condition, Bob encouraged her to get into the practice of composting. We’ve all heard the term, but what exactly is it?

Composting is actually a pretty old practice, dating back to the Romans! People still think it’s beneficial today, and they collect lots of extra organic matter from their property or farm to intentionally let it decompose. The benefit is that the soil stays healthy with this natural turn over of nutrients returning to the earth. Bob showed her exactly how planting diverse agriculture and using its excess green waste could improve her farm in an environmentally friendly way. Very impressive!

Balance and Harmony

Oprah openly shared her dieting struggles for decades with her American audience, and the nation followed her successes and failures. Shockingly, she once consumed only liquids for four months straight! Although she did lose weight, it was obviously not a sustainable lifestyle. No one can blame her! So what is her outlook these days?

Chris Craymer

Oprah says that her goal is no longer just to be thin. After experiencing some health problems a few years ago, she decided that her priorities needed to change entirely. With the help of Bob Greene, the new concept is to be truly strong, fit, and healthy! Her diet these days can be completely sourced from her very own farm. Oprah’s normal everyday sandwich for breakfast sounds delicious: Toasted whole wheat bread with avocado, tomato, and an easy over egg!


A Mountain Escape

When it’s time for a chilly break, Oprah’s got that covered, too. In the mountains of Colorado sits an extraordinary property that has to be seen to be believed! Businessman Bob Wall spent five years designing a sort of high tech treehouse with luxury features and countless rooms to host guests for mountain retreats. What did $14 million get Oprah this time?

Colorado Tourism Office

Five bedrooms sit on 3.25 acres near Telluride, an area where she plans to build another property in the future. While she scouts available land, she has a lot to enjoy! A theater room with a projector in a stone wall inside is just one of the cool features.

High Tech in the Trees

There’s more! A heated driveway that actually keeps the snow away and a watering system for plants while she is out of town can be controlled from a mobile device. An observation deck and a $150,000 glass bridge hallway actually changes color while she walks around this 8,700-square foot house!

Joshua Johnson Photography

What’s more, sensors notify her when anyone is pulling up to the house. Don’t even try to sneak through the trees! Unsurprisingly, cameras monitor everything going on to provide a real sense of privacy and serenity deep in the Colorado woods.


An Enchanted Bridge

Snaking through the trees surrounding her home is an amazing bridge that cost her an estimated $140,000 paired with a special deck 35 feet in the air. At the end of this treetop structure is a gas powered fireplace that also utilizes black lava rocks. Telluride can get pretty icy at times, so a private fire in the trees sounds just delightful!

Joshua Johnson Photography

Oprah spent her formative years in Milwaukee and then her professional years in Chicago — so she is not exactly a stranger to the cold! Telluride regularly reaches temperatures below zero in the winter, and the area gets a lot of rain and snow all year because of its high altitude. 159 inches of snow per year, in fact!

Artistic Inspiration

There are superbly gorgeous mountain views available in 360 degrees throughout the home, as well as from the observation tower made of glass. Few have the chance to see the San Sophia mountain range from so many angles! But what about inside the house? What beauty does Oprah have to enjoy in her everyday living spaces?

Joshua Johnson Photography

The property was already furnished by its previous owner, and it turns out he was a serious African art collector! When he sold the home to Oprah, she inherited a truly unique set of paintings and sculptures. Oprah actually maintains a real connection to the continent beyond art appreciation, having funded a special school for disadvantaged girls from her own fortune in South Africa. It’s easy to sit back and relax in this gorgeous home knowing she is making a difference in real lives of girls across the world.


Cooking Up a Storm

The kitchen in this home is very spacious with plenty of room to walk around during food prep on both sides of its island with a sink. Here, stainless steel was chosen — now often the choice for high end kitchens in contemporary home design.

Joshua Johnson Photography

Stainless steel is actually considered a green kitchen material because it recyclable and does not require extreme chemicals to routinely clean it. The wood surrounding her countertops and appliances creates a warmth in the room and seems like a truly sleek modern space for this mountain home! Very nice, Oprah!

Majestic Colorado

This luxurious observation point on the top floor has large windows, like the rest of the home. Many other rooms were created using stone, but this area is adorned with gorgeous wood that retains its raw natural aesthetics. An ideal contrast with the trees outside!


While Oprah is definitely safe way up high here, the town of Telluride sometimes suffers from avalanches! An extensive education program has started in area schools to help children avoid the dangers while hiking on trails. Hopefully Oprah is signed up, too!


Wine, Anyone?

A unique feature that probably hasn’t been created in any other luxury home is this crazy 56-foot wine cellar that was intentionally designed to look like a local mineshaft. Many may not be aware that gold mining was key to establishing the original economy of Colorado way back in 1858!

Joshua Johnson Photography

An Antique mine cart made of steel runs through the hall of the cellar, and the space stores more than 1,600 wine bottles! But that’s not all. Shockingly, a sound system was installed to broadcast the sounds of dripping water and mysterious creaking noises! Even the lights are programmed to flicker like they might have 100 years ago! This is truly the most unique feature of this mountain mansion, but there are still a few more surprises that Oprah was undoubtedly drawn to when contemplating the property. What could they be?

No-Trouble Bubbles

As she has established with her previous homes, the quality of her bathing experience is no joking matter. This time, she certainly has a few interesting options!

Joshua Johnson Photography

First, a $70,000 limestone tub has high tech features that never let the water get cold! When she wants to relax, she also has the second option of using a private super-hot Finnish sauna. And third, she can lie back in her swirling hot tub in a completely glassed-in enclosure, high in the trees. The glass opens, if she is in the mood. Fun fact: Oprah’s latest recommendation on this topic is a bubble bath with white tea and honeysuckle. Sounds amazing, especially with this view!


All Aboard!

If that crazy house wasn’t enough, Oprah has a $240,000 private tram that takes her directly to the ski slopes! The ride only takes one minute, and then she is ready to zoom around the mountains.

Texas Monthly Magazine

High peaks in the area can be measured at elevations of 14,000 feet! The mountain range itself is notoriously gorgeous, and the Telluride Ski Resort has been consistently ranked number one in America by Condé Nast Traveler readers year after year. Not bad, not bad! If Oprah feels like hosting guests for a ski trip, they can also enjoy the surrounding area with its many award-winning restaurants offering cuisine — vegan, Mexican, and everything in between!


Right in between Seattle and Vancouver, Orcas Island is located in northwestern Washington state. It is the largest of the San Juan Islands, and it seems Oprah took a serious interest in the area in recent years with a major property purchase. But why? Even the town’s residents are not quite sure, but it could be because the islands are becoming a hotspot for eco-tourism!

Wally Gudgell

Like some of her other properties, this estate has a grand name: Madroneagle. She purchased it for $8.275 million, and it sits on 43 acres with several spacious structures. The main house is already 7,303 square feet, but a gazebo, craft shed, tea house, barn, and guesthouse make this buy an impressive one! Let’s take a closer look, shall we?


Northwest Luxury

Built in 2007, the main house is three stories tall and offers 7,303 square feet of space! Stone, slate, wood, and copper make up the exterior of the structure. Inside, four bedrooms and five bathrooms offer plenty of space for Oprah and Steadman to relax. There are many other interesting amenities to keep them healthy and entertained. Let’s take a peek now!

Wally Gudgell

A gym, woodworking shop, and yoga studio are becoming the standard at this point for Oprah and all of her luxurious properties. Outside, a pond and an asian garden offer serenity when they are not relaxing in the teahouse on the left.

Meeting the Locals

Although she is not native to the area at all, Oprah is starting to make her connections with the community. A few years ago, she held a special event at the KeyArena in Seattle. “The Life You Want Weekend” included inspirational personalities like Iyanla Vanzant and Elizabeth Gilbert. Perhaps this lovely and bright outdoor area will be a great place in the future to brainstorm more local empowerment initiatives!

Windermere Real Estate

A perfect little breakfast table is here for coffee talk, and a hallway leads directly to the other side of the backyard. Oprah challenged the crowd to visualize the life they want and asked them to picture their ideal house and the scenery surrounding it. Perhaps Madroneagle is a good place to start!


The Grandest Staircase

Entering the house, it is astonishing how high the ceilings are! Wooden beams decorate the room, and it almost seems like a forest cabin. A special detail that was personalized is the wooden floor, because the material was actually imported from the old Sears building back in Chicago! This particular home showcases unique art from local indigenous peoples of the northwest region. Newer rugs and other accessories match many original pieces!

Windermere Real Estate

The grand living room connects to outdoor patios, as well as the dining room and kitchen. Different species of wood and sturdy iron were used through the room for a truly rustic and authentic design. Some of it was taken from old factories in Seattle! For extra fun, there is a wood-fired pizza oven! Rumor has it that Beecher’s Handmade Cheese is her favorite Seattle shop right now, located at Pike Place Market.

Soup’s On

This absolutely gorgeous kitchen completes the home with modern appliances to cook anything Oprah wants. And it turns out that what Oprah wants is soup!

Cottages & Gardens

Apparently, she has some type of soup almost every day. And in the cool climate of the northwestern United States, this may be the perfect kitchen to get creative with recipes. Oprah says that soup fills her with a sense of well-being — “comfort in a bowl” — good for her body and soul. The winner seems to be tomato: She says she has never found a tomato soup she doesn’t like.


Tea Time, Tree Time

Outside on the property, Oprah can enjoy 3,000 feet of shoreline! Overlooking the water is the teahouse, which has a patio and a firepit. Also near the water is the 2,948-square-foot guest house on a cliff! A private beach just steps away is undoubtedly the cherry on top of this absolutely marvelous estate.

Wally Gudgell

Shockingly, Oprah has never visited Madroneagle! How can this be? Perhaps it is merely an investment property, but it is possible she will start using it in the future. When she does, the local area has a superb wine scene and new mountains to explore!

The Windy City

Chicago is one of America’s greatest cities, but not everyone has visited it yet! What do residents enjoy every day of the week? To start, the city itself is pretty big: 237 square miles! The population is currently about 2.7 million, and this is surrounded by endless suburbs that make up the giant metropolitan area.


Entertainment in the city includes more than 5,195 restaurants, 200 dance companies, 225 music venues, and more! Unlike some large cities, Chicago also has the benefit of 8,100 acres of public green space and access to the Lake Michigan beach. With all of this to keep her occupied after work, it’s not hard to see why Oprah chose this location for the long term production of her show!


Chicago Memories

During this period, Oprah did not primarily live in a sprawling mansion. She enjoyed city life they way city dwellers must in a luxury highrise in downtown Chicago. Just a few years ago in 2014, she finally put the property up for sale! The famous Water Tower Place building is coveted real estate, and she occupied a duplex on the 56th floor.

Brookfield Properties

This listing for $7.75 million had amazing views of the lake and plenty of light in its two kitchens, numerous bedrooms, and private library. In total, 9,625 square feet held four bedrooms with six bathrooms. In a place with as much scarcity for space as Chicago, this one was really a gem!

What Next?

Although her new OWN Network has already had plenty of impressive success with new hit shows like Iyanla: Fix My Life, Oprah is never done raising the bar. Apple announced a new partnership with America’s favorite interviewer, expanding her book club to the most advanced platform out there!

The Verge

She has also been working on a documentary called “Toxic Labor,” and hopes to bring attention to the issues of harassment and mental health to millions of viewers. She may already have a huge audience on her network, but Apple will multiply that tenfold! Looks like Oprah has been pretty busy outside of collecting investment properties and digging up fancy organic produce with her own hands! Where does she find the time and energy? Oprah is truly one of a kind!