 Welcome to Madronigal, a matchless land portfolio and residential sanctuary arrived to a grand two-story atrium with a towering fireplace and abundant natural light. In September 2022, Oprah Winfrey decided to sell one of her large estates in Monocito, California in two separate transactions which combined for around 17 million dollars. She purchased the property only a year earlier in 2021 for 10.5 million dollars and has sold each parcel to friends of hers, one being Jennifer Aniston who purchased the Mediterranean main house property for almost 14.8 million dollars. A far cry from the Mississippi Woodshack Oprah grew up in, she now presides over a handful of multi-million dollar homes in her real estate portfolio. The successful billionaire continues to own the 30 million dollar compound beside the spot she recently sold to Aniston and of course her main residence called Promise Land which is a sprawling 66 acre estate with 20,000 square foot mansion also in Monocito. And those are just a couple of Oprah's properties. Also Michael and I have dropped our own house tour of our new home that we moved into this year so go ahead and subscribe to our personal channel if you want to see where we're living and more of what we're up to. In these videos we don't reveal any addresses and even though I've done a house tour of my own place please do not show up at any private residences because it's not safe for anyone. While Oprah Winfrey lords over multiple homes she added one to her portfolio in 2021 but offloaded it just a couple of months ago to a particularly famous friend. In early 2021 the media mogul dished out a reported 10.5 million dollars on a multi-parcel spread in her favorite area of Monocito California which she bought off of New York hedge fund manager Fred Schumann and his wife. They're the ones who put together the 2.1 acre spread over many years. Recently Monocito has become a hot spot for celebrity real estate where the likes of famous home flippers such as Ellen DeGeneres and Adam Levine have collected fortunes from buying and selling some of the area's richest estates. We also know that Oprah herself loves Monocito due to the fact that she owns multiple properties here including her long-time main residence Promised Land. This property which Oprah recently sold in two separate transactions included a Mediterranean main mansion, two small cottages and stunning grounds. The two transactions of her property reportedly earned Oprah a total of around 17 million dollars. She split the estate in two and both buyers were her friends. The first sale going through in mid-August 2022 which was the half with the small cottages selling for $2.3 million to her personal trainer and property manager Bob Green. Then a week later or so Oprah sold the other half which included the main Mediterranean mansion to none other than her actress friend Jennifer Aniston for nearly $14.8 million. Sadly there are no interior photos of the home gen purchased from Oprah but we do know the villa's documents show some details. Built in 1998 the home which is reportedly a Tuscan style farmhouse underwent a major renovation in 2008 after the last owners purchased it. Today the mansion is built in a bit of a U-shape and offers over 4,000 square feet of space along with four bedrooms, three full baths and one half bath. There is also a small detached guest house or structure which could be an office or standalone gym on the very private one acre property which is also shrouded by plenty of woods and foliage. Jen's new estate further boasts grassy lawns, manicured gardens, entertaining terraces, mature oak trees and a driveway and motor court with room for 15 cars or more. This long driveway is gated for more privacy while the home itself can't be seen from the street. Finally the home also has the bonus of panoramic ocean and mountain views according to an old listing material for the property. Oprah still owns many other homes including the massive estate next door to this one which is a 30 million dollar compound purchased in 2012. Not to mention her main residence the 66 acre promise land is also in Monocito so let's take a look at that one next. Way back in 2001 Oprah was invited to a party at a dreamy estate in the picture perfect neighborhood of Monocito near Santa Barbara and the rest was history. She fell in love with the peaceful 42 acre property so much that she persuaded the owners Robert and Marlene Vellos to sell the place even though it wasn't on the market. Oprah wrote up a check for about 52 million dollars and began making this place now called the promise land her very own. She named the property this to symbolize her journey from rags to riches as it's taken from a biblical reference for an African-American woman living in paradise whose ancestors were slaves. Oprah's home is decidedly paradise estimated to be worth about a hundred million dollars these days after several additions. The main mansion was built in 1912 originally but underwent extensive renovations to make it its current size of 23 thousand square feet and to suit Oprah's specific tastes. There are more than six beds and 14 baths throughout as well as 10 cozy fireplaces. While Oprah bought the main property back in 2001 later in 2016 she purchased a piece of land known as Seamer Farm spanning over 23 acres directly beside it for over 28 million dollars. This additional property boasts a 5,000 square foot ranch style home, a pool, horse stables, caretaker cabin, equestrian ring and even orchards. Furthermore, Oprah bought another 44 acre preserve on the other side of her property to get the ultimate privacy. These days the Promised Land spans over 70 acres near the beaches and the mountains. Oprah's main home is designed in a classic neo-Georgian style and the main entryway has a winding staircase and high ceilings. Personalized with photos of loved ones so the star can see them upon first walking into her house. In fact, as her forever home Promised Land is where Oprah and her long-term partner Stedman Graham love to spend time and they have decorated the place full of mementos, books and artwork. The home has been thoughtfully put together over the years and Oprah runs her business empire from the property too. When she's unwinding sometimes she even posts pics hanging with her dogs here on Instagram. The kitchen is the heart of Oprah's mansion and it's a spot where she and her loved ones can get together and kick back. The TV icon had the fireplace and pizza oven removed to create more space here but left the rest as it was. Altogether her mansion boasts several living rooms, a library, kitchen, two movie theaters, an office and a wine cellar. Also on Oprah's property she has a fully redecorated and elegant guest house as well as a tea house. Her tea house is set right in the middle of the garden and it was originally built as a place to cut flowers but she changed her mind and made it a space for herself. She also said she comes to the tea house to read, meditate and enjoy a cup of tea. The grounds of Oprah's mansion are truly a sanctuary with perfectly manicured lawns, gardens with roses and lilies and amazing views of the ocean and mountaintops. On one of the combined properties Oprah also has a large pool surrounded by palm trees, a gorgeous patio and nearby a koi pond all creating the perfect space to entertain or relax. In 2019 Oprah also reportedly bought another home in Montecito off of actor Jeff Bridges. This property spans 4 acres and is next to her main estate costing her $6.9 million dollars. Bridges apparently spent a fortune remodeling the Spanish revival style so it was a surprise he didn't hike up the price to sell it to Oprah considering he bought it for basically the same price in 2014. Either way this home was tastefully restored offering common rooms like a living area with white walls, vaulted wood ceilings, large windows and a cozy fireplace. The rustic yet minimalistic style continues in the kitchen where there's a wooden ceiling with skylights, custom wood cabinets to match and a marble topped island. Over in the master suite there are exposed beams, bay windows and French doors out to the yard along with highlights like a massive walk-in closet, an en suite with soaking tub and more. Out on the grounds of this property you'll find a swimming pool and spa area, a pool house, a carriage house that's been transformed into an art studio as well as a red brick terrace to lounge or entertain. Prior to securing this place in 2018 Oprah decided to purchase another peaceful and picturesque property. This one not in Montecito. Tucked between Seattle and Vancouver there are the San Juan Islands made up of four main islands accessible by Washington state ferries. One of these is Orca's Island where Oprah snagged a 43 acre compound called the Madron Eagle Estate. Oprah's getaway here is completely private with two waterfront pieces of land and 3,000 feet of shoreline. It costs her 8.2 million dollars for this expansive property and inside the residence measures in it over 7,300 square feet with four beds, three full baths and two half baths. The main residence is three floors and made with stone accents and natural woods used throughout which create the all-american luxury cabin feel. As you enter the home you're greeted by a massive hanging art piece that frames the entryway and sets the stage for what's to come. The main level is home to the kitchen with pizza oven and skylights, living room, dining area and bedrooms. Oprah's master suite features a stone wall with wood accents and a marble spa like en suite. There's also a library corner in the home with floor-to-ceiling bookshelves which I'm sure is a feature book-loving Oprah takes advantage of. Also on the lower level there's a home office complex, wine cellar and a tasting room. A custom-built staircase leads to the upper level where there's a huge bonus room or family room as well as a fully stocked games room. Outside is as lush as you might expect with native trees and plants manicured perfectly. Stone paths weave through the gardens which completes the peaceful earthy landscape and that's not all. Of course Oprah also needs room for her traveling entourage which the gallery house is perfect for. The contemporary guest house on the property is just under 3,000 square feet and has four beds and three baths all set on a high cliff perched above a private beach. Other features on her Orca's Island property include a tea house underneath the trees and overlooking the water. A huge barn with a woodworking studio up top and a gym and yoga studio on the lower level. Elsewhere there's a sauna, garden, pond and stream, private hiking trails and a private beach. While these are not all of the stunning properties that Oprah Winfrey owns it definitely gives you a taste of this billionaire's real estate portfolio. For today though that'll bring this house tour to an end. But before we go answer me this, if you already had a mega main house in your home state where would you get your first vacation property if you could choose to get one anywhere in the mountains or on the beach or somewhere else? Let me know your dream getaway location in the comments down below. Otherwise like, subscribe and turn on your notifications to make sure you never miss a video. My name is Cara the Vampire Slayer, follow me on Instagram to chat more and I'll see you all in another one. Bye!