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. Kicking off with Queen O's magnificent Montecito estate she named Promised Land, we take you on a tour of the superstar billionaire's picture-perfect homes and there are a few surprises in store...

Worth more than $100 million (£81m) 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.

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. 

In order 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 colour scheme, cream New England-style dresser and comfy upholstered chairs.

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 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 love of curated curios and nature is perfectly captured in this little tabletop display at her Maui holme. Fresh fern leaves and a scented candle sit next to a frame in her favourite cream colour. We love the wall sconce too!

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 (£11.4m) in a deal that included all furnishings.

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.

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.

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 ambience.

Other highlights of the ultra-modern property include a $150,000 (£122k) glass walkway with fibre optic lights that change colour, a bathroom that contains a $70,000 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 (£195k).

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 (£23.5m) to acquire the estate, which contains a single-storey ranch house that was designed by architect Cliff May and completed in 1955.

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.

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.

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.

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 next big real estate buy came in the summer of 2018 when the billionaire media magnate paid a bargain $8.3 million (£6.7m) 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 (£9.8m). 

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.

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.

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. 

Book-loving Oprah would have obviously been very taken with the home's snug reading nook. The comfy space, which is fitted with a number of 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.

The home's bedrooms are just as cosy and this one delights with heart-stopping waterfront views. Madroneagle's other selling points, which Oprah clearly couldn't resist, include a wine cellar, fitness centre and music studio. Reports suggest the Queen of All Media plans to stay at the property at least two weeks per year.

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.

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 centre island. Like the impeccable living room, the kitchen is simple and minimal though manages to be a warm and inviting space.

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.

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. 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 two vacation homes in the Caribbean, and possibly additional holdings we don't know about. We're impressed!