Tour the Queen of TV’s spectacular residences
A far cry from the Mississippi wood-frame shack she grew up in, Oprah Winfrey now has numerous stunning multimillion-dollar residential properties in her bulging real estate portfolio and is said to be worth $3.5 billion (£3bn). The media mogul, philanthropist, and actress has bought and sold several amazing properties over the years, including most recently to a particularly famous Friend. Click or scroll to see inside her collection of picture-perfect homes…
Oprah’s Promised Land estate main house, Montecito, California
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Back in 2001 Oprah was invited to a party at this dreamy estate in the idyllic village of Montecito near Santa Barbara and instantly fell in love with the tranquil 42-acre property, so much so that she used her formidable powers of persuasion to get the owners Robert and Marlene Veloz to sell up—the estate wasn’t actually on the market—and wasted no time writing out a cheque for almost $52 million (£43m).
Oprah’s Promised Land estate main house, Montecito, California
Google Earth
Worth more than $100 million (£82.5m) today, the glorious Promised Land estate spans 70 acres thanks to some canny deals on neighboring properties. At its center is Oprah’s 23,000-square-foot mansion, an impressive neo-Georgian pile, and the amazing landscaped grounds include rose gardens, terraces, and fountains.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
As her forever home, Promised Land is where Oprah and her long-term boyfriend Stedman Graham love to spend time. Beautifully decorated and filled with mementos, books, and artwork, it’s been lovingly put together over the years. Oprah runs her business empire from here too and is often posting pictures at home with her dogs on her Instagram page.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
To make the dining room space more welcoming and relaxing, Oprah gave it—and the rest of the mansion—a huge makeover. Out went striped wallpaper and ornate antique furniture, replaced with a beige color scheme, cream New England-style dresser, and comfy upholstered chairs.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
The kitchen is the heart of Oprah’s mansion, a place where her friends can congregate and kick back. The TV legend had the fireplace and pizza oven removed to free up more space but left everything else as it was.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
All in all the mansion boasts several living rooms, a library, a kitchen, two home theatres, a wine cellar, an office, six bedrooms, and 14 bathrooms. Seen here on New Year’s Eve 2021, Oprah posted a video to her Instagram showing another glimpse of her fabulous dining table topped with Haitian food cooked by chef, Gregory Gourdet.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
For Winfrey’s 2022 New Year’s Day brunch she posted another video walking from her beautifully revamped dining room through to a bright and airy sun room, brimming with large potted plants and awash with shutter-styled walls. The tables were laden with fresh fruit, pastries, and tasty buns.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
As you can imagine, celebrities love a walk-in wardrobe and Oprah is no different. With regular TV appearances and public appearances for her charity work and many business ventures, the media mogul needs to look the part. This smart room with fitted cabinets is where she stores her extensive clothing collection and she regularly shares videos with her followers while she’s packing for one of her many trips around the world.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
Oprah’s renowned love of books makes itself felt in almost every room of the house, including her beautiful study. In addition to the sprawling neo-Georgian mansion, Oprah’s estate comprises orchards, a koi pond, tennis courts, a pool and pool house, as well as a two-bedroom Craftsman-style guest house spanning 4,000 square feet.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
For Thanksgiving 2022, Oprah and friends stood outside her front door and sang a welcoming African song “for newcomer Paul, spouse to daughter-girl Palesa” according to the Instagram caption, as part of a yearly tradition. “Thanksgiving is in full force here” Winfrey types, followed by three turkey emojis.
Oprah’s Promised Land estate main house, Montecito, California
@oprah / Instagram
Last Christmas Oprah hosted a cozy movie night from her Promised Land home cinema room, settling down with Stedman Graham and friends to watch the film Swan Song on large cream chaise lounges with thick blankets. We look forward to more festive updates this year from her magical Montecito estate.
Royal guests
@CBA / YouTube
Of course, who can forget Prince Harry and Meghan Markle’s exclusive interview with close friend and neighbour, Oprah Winfrey? Premiered in March 2021, it took place in a secret location near the couple’s mansion in Montecito, Santa Barbara, just a six-minute drive from Oprah’s Promise Land estate.
Oprah’s Maui estate, Kula, Hawaii
Erik Aeder / Stringer / Getty Images
In 2003 Oprah paid $5.3 million (£4.4m) for two parcels of land on the Hawaiian island of Maui totaling 23.7 acres, not to mention a modest grey farmhouse, which she has since transformed into a ravishing vacation home. Over the years, the TV icon has bought up acres of land and at least a dozen buildings in Maui, and is reported to have spent a total of $60 million (£49.5m) in the process.
Oprah’s Maui estate, Kula, Hawaii
@oprah / Instagram
The Maui estate now spans a colossal 163 acres and in 2010 she was granted permission to run a bed and breakfast on the site by the Maui County Council. Oprah has made use of the fertile ground and amazing climate and now grows fruit, vegetables, and flowers on the site.
Oprah’s Maui estate, Kula, Hawaii
@oprah / Instagram
The highlight of Oprah’s blissful Hawaiian hideaway has got to be the gorgeous farmhouse with its wraparound veranda, which like the terrace on the upper level, makes for the ideal space to while away warm evenings in a rocking chair and take in the exceptional vistas.
Oprah’s Maui estate, Kula, Hawaii
@oprah / Instagram
She also loves hosting family and friends for island vacations. This happy holiday snap of Oprah, Stedman (left), and her friends at Christmas, gives a little glimpse of her signature style, with clean, bright interior decor. Even the tree can’t top it!
Oprah’s Maui estate, Kula, Hawaii
@access / YouTube
Oprah’s love of curated curios and nature is perfectly captured in this little tabletop display at her Maui home. Fresh fern leaves and a scented candle sit next to a frame in her favorite cream color. We love the wall sconce too!
Oprah’s contemporary ski chalet, Telluride, Colorado
Joshua Johnson Photography / Concierge Auctions / Zillow
Oprah snapped up a whopping 60 acres of land in the ski resort of Telluride in Colorado in 2014 and a year later acquired a sensational five-bedroom, six-and-a-half-bathroom contemporary ski chalet, which she bought from tech entrepreneur Bob Wall for $14 million (£11.5m) in a deal that included all furnishings.
Oprah’s contemporary ski chalet, Telluride, Colorado
Joshua Johnson Photography / Concierge Auctions / Zillow
The Queen of TV is an avid skier and has joyfully likened the pastime to being able to fly, so it was only a matter of time before she snagged a home near the slopes. The living room is the most jaw-dropping space in the 8,700-square-foot property. It wows with a double-height ceiling with wood paneling, dramatic floor-to-ceiling windows, and a huge stone fireplace.
Oprah’s contemporary ski chalet, Telluride, Colorado
Joshua Johnson Photography / Concierge Auctions / Zillow
The house, which has been decked out with state-of-the-art Smart technology that controls everything from the security to the lighting and heating, also features a family room with a library—an essential for its book-loving owner—billiards table and a movie projection screen that drops down from the ceiling and disappears when not in use.
Oprah’s contemporary ski chalet, Telluride, Colorado
Joshua Johnson Photography / Concierge Auctions / Zillow
Rocking fine wood cabinetry and stainless-steel countertops, the open-plan kitchen is nice and spacious. Exposed steel beams lend the space a hip industrial feel though the warm wood cupboards and rustic stone wall prevent it from looking cold and clinical. The kitchen leads into a dining area that can seat up to eight people.
Oprah’s contemporary ski chalet, Telluride, Colorado
Joshua Johnson Photography / Concierge Auctions / Zillow
Talk about a house with a secret! It comes with a fabulous wine mine which is its pièce-de-résistance. The 56-foot cellar, which can store up to 1,600 bottles, was designed to resemble an old mine. It delights with a rusty old ore car and track and is tricked out with a sound system that plays sounds of dripping water and creaking wood to add to the ambiance.
Oprah’s contemporary ski chalet, Telluride, Colorado
Joshua Johnson Photography / Concierge Auctions / Zillow
Other highlights of the ultra-modern property include a $150,000 (£124k) glass walkway with fiber optic lights that change color, a bathroom that contains a $70,000 (£57k) tub with an inline heating system that keeps water consistently warm, a smoke sauna and best of all, a private funicular railway that is reported to have cost $240,000 (£198k).
Oprah’s Seamair Farm, Montecito, California
Marty Rogers / Sage Auctions
Oprah expanded her Montecito real estate portfolio in December 2016 when she purchased the neighboring property, a 23-acre equestrian estate called Seamair Farm. The talk shows luminary parted with $28.9 million (£23.8m) to acquire the estate, which contains a single-story ranch house that was designed by architect Cliff May and completed in 1955.
Oprah’s Seamair Farm, Montecito, California
Marty Rogers / Sage Auctions
May has been dubbed the Father of the Californian ranch house, which is considered the postwar suburban dream home, and Oprah’s pad is an excellent example of the style he developed. The mid-century masterpiece has a wood-siding-clad exterior and an open-concept interior with four bedrooms, five-and-half bathrooms, a wine cellar, and a total of four fireplaces.
Oprah’s Seamair Farm, Montecito, California
Marty Rogers / Sage Auctions
Given Oprah owns a sizable mansion next door, it’s unlikely she lives in the house, which is probably used as office space, staff quarters or to accommodate the many guests she welcomes. They are bound to appreciate the ranch house’s secluded swimming pool, which is surrounded by a lush tropical-inspired garden.
Oprah’s Seamair Farm, Montecito, California
Marty Rogers / Sage Auctions
The property also features three bijou residences that are no doubt used to house staff or guests. The estate’s equestrian facilities are top-notch and have been meticulously maintained as you can see from this shot of one of the riding rings. Note the manicured lawns and octagonal gazebo at its center.
Oprah’s Seamair Farm, Montecito, California
Marty Rogers / Sage Auctions
In addition to the riding rings, the property contains numerous paddocks and a multi-stall stable, which has to make it one of the finest equestrian estates for miles around. Other features of the property include a two-acre avocado grove and orchard with plenty of fragrant fruit trees.
Oprah’s Seamair Farm, Montecito, California
Marty Rogers / Sage Auctions
The cherry on the cake is this picturesque koi pond with lush water-loving reeds and ornamental touches. The property also came with two private water wells to boot, very useful for keeping things green during the hot California summers.
Oprah’s Madroneagle retreat, Orcas Island, Washington
Wally Gudgell / Windermere Real Estate
Oprah’s next big real estate buy came in the summer of 2018 when the billionaire media magnate paid a bargain $8.3 million (£6m) for a 43-acre waterfront estate called Madroneagle on Washington’s Orcas Island, a magnet for the ultra-wealthy craving peace and solitude. The property, which was first put on the market in 2016, was listed for just under $12 million (£9.9m).
Oprah’s Madroneagle retreat, Orcas Island, Washington
Wally Gudgell / Windermere Real Estate
Former owner Kathleen Dickinson McDowell was by all accounts thrilled to sell the property to Oprah who she felt would be a great caretaker. Blending in beautifully with its surroundings, the main 8,000-square-foot house, which was designed by Dickinson McDowell and her late husband, was built using reclaimed wood and local sandstone, making it a wonderfully sustainable home.
Oprah’s Madroneagle retreat, Orcas Island, Washington
Wally Gudgell / Windermere Real Estate
The eco mansion, which is nestled within a calming Asian-style garden, has a total of four bedrooms and five bathrooms and looks out onto its very own beach. The home’s open-plan living room is simply divine. The high-ceilinged space seriously impresses with reclaimed beams, exposed stone walls, and an enormous fireplace. Interestingly, the floorboards were gleaned from the original Sears building in Oprah’s former stomping ground in Chicago.
Oprah’s Madroneagle retreat, Orcas Island, Washington
Wally Gudgell / Windermere Real Estate
The kitchen is Oprah-worthy and hands-down a fantastic space for the TV tycoon to hone her culinary skills – cooking is one of her favorite hobbies after all. Its standout features range from an enormous wood-fired pizza oven to a massive center island and charmingly mismatched country-style cabinetry.
Oprah’s Madroneagle retreat, Orcas Island, Washington
Wally Gudgell / Windermere Real Estate
Book-loving Oprah would have been very taken with the home’s snug reading nook. The comfy space, which is fitted with several capacious bookcases and dressers, looks like an exceedingly pleasant space in which to get lost in a gripping novel or flick through a magazine or two.
Oprah’s Madroneagle retreat, Orcas Island, Washington
Wally Gudgell / Windermere Real Estate
The home’s bedrooms are just as cozy and this one delights with heart-stopping waterfront views. In 2021, Oprah sold her stunning estate in an off-market deal for a reported $14 million (£11.5m). Wally Gudgell, the agent who represented Oprah in the sale, reportedly said, “They were in the process of remodeling and they just realized in that process they were never going to be able to use it properly and it doesn’t make any sense.” While the property was not formally listed, the deal marks the highest price ever paid for an Orcas Island property, sources familiar with the sale told the Biz Journal.
Oprah’s Spanish Revival estate, Montecito, California
Eric Foote / Elevated Horizon / Coldwell Banker
Oprah then acquired actor Jeff Bridges’ former home in Montecito. Like Seamair Farm, the ranch, which spans four acres, borders the Promised Land estate. The TV legend clinched the deal in November 2019, paying just under $6.9 million (£5.7m) to secure the property adjacent to her own.
Oprah’s Spanish Revival estate, Montecito, California
Eric Foote / Elevated Horizon / Coldwell Banker
Oprah got herself another bargain having paid the same price Bridges bought the ranch for in 2014, though the actor spent a fortune remodeling the Spanish Revival home following a landslide in 2018 that caused extensive damage. The property was originally listed by Bridges for almost $8 million (£6.6m).
Oprah’s Spanish Revival estate, Montecito, California
Eric Foote / Elevated Horizon / Coldwell Banker
Bridges carried out a tasteful restoration of the house, which was designed by celebrated Californian architect James Osbourne Graig and constructed in 1919. This living room with its whitewashed walls, vaulted wooden ceiling, large lattice windows, and generously sized fireplace has a minimal, elegant yet cozy feel.
Oprah’s Spanish Revival estate, Montecito, California
Eric Foote / Elevated Horizon / Coldwell Banker
The rustic yet pared-back style continues in the kitchen. We’re sure Oprah adores the wooden ceiling that features several skylights, along with the custom wood cabinetry and the marble-topped center island. Like the impeccable living room, the kitchen is simple and minimal though manages to be a warm and inviting space.
Oprah’s Spanish Revival estate, Montecito, California
Eric Foote / Elevated Horizon / Coldwell Banker
The classy theme carries into the master suite. The room enchants with exposed beams, bay windows, and French doors that lead into the blissful backyard. The suite also features a supersized walk-in wardrobe and bathroom, which contains a deep-soaking tub to relax and unwind in.
Oprah’s Spanish Revival estate, Montecito, California
Eric Foote / Elevated Horizon / Coldwell Banker
Outside there’s a pool and spa area, pool house, and red brick terrace, as well as a carriage house that serves as an art studio, and an all-important private well. But Winfrey didn’t stop there, adding to her Montecito property collection just two years later…
Oprah’s Tuscan-style farmhouse, Montecito, California
Google Maps
In early 2021, the Queen of Daytime TV splurged on another Montecito residence. Splashing out a reported $10.5 million (£8.7m) on a Tuscan-style farmhouse complete with two cottages, Oprah will have enjoyed panoramic ocean views and a driveway surrounded by lush landscaping according to the NY Post. But does she still live there?
Oprah’s Tuscan-style farmhouse, Montecito, California
Google Maps
Oprah’s Montecito home caught the eye of another VIP, who even went so far as to snap it up in August 2022 in an off-market deal—roughly eighteen months after Oprah purchased it herself. The NY Post reported that none other than Jennifer Aniston splashed out just under $14.8 million (£12m) on the Tuscan-style farmhouse main residence, while Winfrey’s longtime personal trainer bought the other half of the estate—comprising of two cottages—for $2.3 million (£1.9m), providing Oprah with an impressive $6.5 million (£5.3m) profit.
What’s on the horizon for Oprah?
@oprah / Instagram
On top of the real estate eye candy we’ve featured, Oprah is said to own a couple of modest properties in Chicago and Nashville, as well as possibly additional holdings we don’t know about. Here she enjoys some chef-made coconut and pineapple-soaked birthday cake in her Montecito garden under a fabulous fringed sun hat. We can’t wait to see what other properties our favorite host might decide to flip or keep!