Promised Land: inside Oprah’s $100 million+ home and property portfolio (2024)

Marty Rogers / Sage Auctions ; Jon Kopaloff / Stringer / Getty Images

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 (£2.7bn).

The actress and former talk-show host has built an enviable empire over the years and a network of endeavours tied to philanthropy and media production and distribution. She turned 70 in January 2024, but shows no signs of slowing down…

@oprah / Instagram

One of her most recent ventures includes producing a new film version of The Color Purple which was released in December 2023.

Oprah played Sofia in Steven Spielberg’s 1985 movie, an adaptation of Alice Walker’s novel, and she is seen here alongside Danielle Brooks, who plays Sofia in the new movie.

The star has also been awarded aLifetime Achievement Award from GLAAD, the Gay and Lesbian Alliance Against Defamation, for her constant support in the struggle for equality.

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A new svelt Oprahrevealedlate 2023 that she has been taking weight-loss medication to maintain a healthy weight long-term. “I’m absolutely done with the shaming from other people and particularly myself,” she told People.

She announced in February 2024she was leaving WeightWatchers and giving away all her stock, reports The Guardian. The public face of the organisation since 2015, Oprah said she wanted to “eliminate any perceived conflict of interest around her taking weight-loss medications” and would donate her estimated $18 million (£14m) stake in the company to the National Museum of African American History and Culture.

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If she ever decides it's all too much and she needs to step back, she'll bespoilt for choice in terms of hideaway retreats.

Back in 2001 Oprah bought her Promised Land estatein Montecitoafter attending a party here and instantly falling in love with thetranquil 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, but Oprahwasted no time writing out a cheque for almost $52 million (£40.8m), say reports.

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Worth more than $100 million (£78m) today, the glorious Promised Land estate spans 70 acres thanks to some canny deals on neighbouring properties.

At its centre 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 / 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 mementoes, 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 / Instagram

Oprah has been hands on when it comes to giving the house a complete makeover.

In order to make the dining room amore relaxed and welcoming space, she ripped out the striped wallpaper and ornate antique furniture, replacingthem with a beige colour scheme, cream New England-style dresser and comfy upholstered chairs.

@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 / Instagram

All in all the mansion boasts several living rooms, a library, 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 / Instagram

@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 herextensive clothing collection and she regularly shares videos with her followers while she's packing for one of her many trips around the world.

@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 comprisesorchards, 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 / Instagram

Oprah regularly reveals hidden corners of her estate, for instance when she was launching her book on happiness, Build the Life You Want in November 2023.

Sitting on a green wicker sofa upholstered with country-style cushions, the business woman chatted with co-author and social scientist Arthur Brooks about how tofind contentment in life.

@oprah / Instagram

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 to the couple's mansion in Montecito, Santa Barbara, just a six-minute drive from Oprah's Promise Land estate.

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In 2003 Oprah paid $5.3 million (£4.1m) fortwo parcels of land on the Hawaiian island of Maui totalling 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 / 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 / Instagram

@oprah / Instagram

@oprah / Instagram

It was her friend Bob, according to reports, that convinced her to buy land in Maui.

She has introduced many of her pals to the region since, including fellow TV star Gayle King, who joined Oprah for a spot of hiking in the hills in Kauai in 2023, to show off her “new knees”. Oprah had double knee surgeries in 2021.

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The star was devastated in 2023 when wildfires ravaged the Hawaiian island and provedthe deadliest of the last century in the US, according to the LA Times.

She teamed up with Dwayne Johnson, who is of Polynesian descent, to launch the People’s Fund of Maui to put money directly into the hands of local residents in need in the wake of the disaster.

Joshua Johnson Photography / Concierge Auctions / Zillow

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 panelling, dramatic floor-to-ceiling windows and a huge stone fireplace.

Joshua Johnson Photography / Concierge Auctions / Zillow

The househas been decked out with state-of-the-art smart technology that controls everything from the security to the lighting and heating.

It also features a family room with a library, an essential for its book-loving owner, as well as a billiards table and a movie projection screen that drops down from the ceiling and disappears when not in use.

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.

Joshua Johnson Photography / Concierge Auctions / Zillow

Talk aboutahouse 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 fitted out with a sound system that plays sounds of dripping water and creaking wood to add to the ambience.

Joshua Johnson Photography / Concierge Auctions / Zillow

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Oprah expanded her Montecito real estate portfolio in December 2016 when she purchased the neighbouring property, a 23-acre equestrian estate called Seamair Farm.

The talkshow luminary parted with $28.9 million (£23.3m) to acquire the estate, which contains a single-storey ranch house that was designed by architect Cliff May and completed in 1955.

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.

Marty Rogers / Sage Auctions

Given Oprah owns a sizable mansion next door, it's unlikely she actually 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.

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 centre.

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.

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.

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Oprah's next big real estate buy came in the summer of 2018 when the billionaire media magnate paid a bargain $8.3 million (£6.5m) 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 (£9.4m).

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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.

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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 of Chicago.

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The kitchen is totally Oprah-worthy and hands-down a fantastic space for the TV tycoon to hone her culinary skills. Cooking is one of her favourite hobbies after all.

Its standout features range from an enormous wood-fired pizza oven to a massive centre island and charmingly mismatched country-style cabinetry.

Realtor.com

Realtor.com

The home's bedrooms are just as cosy 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, theagent who represented Oprah in the sale, reportedlysaid, “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, thedeal marks the highest price ever paid for an Orcas Island property, sources familiar with the sale told the Biz Journal.

Eric Foote / Elevated Horizon / Coldwell Banker

Oprah's 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 inNovember 2019, paying$6.85million (£5.4m) to secure the property adjacent to her own.

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 remodelling the Spanish Revival home following a landslide in 2018 that caused extensive damage.

In fact, the property was originally listed byBridges for almost $8 million (£6.2m).

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 cosy feel.

Eric Foote / Elevated Horizon / Coldwell Banker

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.

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...

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Google Maps

Oprah’s Montecito home caught the eye of another VIP, who snapped it up in August 2022 in an off-market deal, just 18months after Oprah purchased it herself.

The NY Post reported thatJennifer Aniston splashed out just under $14.8 million (£11.7m) on the Tuscan-style farmhouse main residence, while Winfrey’s longtime personal trainer bought the other half of the estate, comprising two cottages, for $2.3 million (£1.8m), providing Oprah with an impressive $6.5 million (£5m) profit.

@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-soakedcake on her 70th birthdayin her Montecito garden under a fabulous fringed sun hat. We can’t wait to see what other properties our favourite host might decide to flip or keep!

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