A Look Inside of Oprah Winfrey House

The influence of Oprah Winfrey is totally unrestricted. According to Forbes, the tycoon had a net worth of $2.5 billion as of 2021 and had established a massive media and philanthropic empire. More specifically, where has this sugar mama been residing since she waved goodbye to those television screens. Oprah Winfrey House Oprah Winfrey’s California It makes sense that Winfrey has established residences for herself in a number of places across the United States given her multiple obligations. Winfrey has lived in Montecito, California, for more than 20 years, but she also has residences in Illinois, Florida, Hawaii, Colorado, and Washington. Although she mostly bought those homes for family and friends, she has also owned or presently owns houses in Indiana and Tennessee. Here, we’ve compiled a selection of Winfrey’s real estate holdings, which are an impressive indication of her wide-ranging preferences and different life phases.

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Winfrey’s purchase of a condo in Chicago’s renowned Water Tower Place, which is situated along the city’s Magnificent Mile, was one of her first significant real estate investments. Although the original purchase price was never made public, the Chicago Tribune reports that she then purchased three additional apartments that were all close to the first one for amounts of $1.0625 million, $1.5 million, and $1 million, respectively. The four units had four bedrooms, five full bathrooms, and two half bathrooms, totaling 9,625 square feet. The large duplex was eventually advertised by Winfrey for $7.75 million in January 2014, and it was eventually sold for $4.625 million in late 2015.

Oprah Winfrey House


Winfrey spent $100,000 on a three-bedroom condominium at the Four Seasons Chicago at about the same time she bought the final of the four adjacent condos at Water Tower Place. The famed luxury hotel is not far from the Near West Side, where Winfrey’s multimedia production firm at the time, Harpo Studios, is located, and a few steps from Lake Michigan. The property was subsequently sold by Winfrey for $1.275 million in 2015, the same year the studios were permanently closed and she moved to the West Coast.


On Fisher Island, a 216-acre man-made island located just off the coast of Miami, Winfrey made a much-discussed acquisition this year. She spent an undisclosed sum on a 6,170 square foot penthouse property with four bedrooms, six bathrooms, 20-foot ceilings, and a sizable oceanfront balcony. The apartment was in the upscale Villa Del Mare condos, which had a billiards club, a bicycle trail, numerous swimming pools, and a spa as facilities. With a wood-burning oven in the kitchen and a roomy master suite with his-and-hers en suite baths and dressing rooms, the house itself was airy and well-lit. In the end, Winfrey sold the property to the former chairman of Campbell’s Soup for a then-unprecedented $6.5 million.


In 2001, Winfrey started putting down roots in her expansive property in Montecito, which has come to be known as the Promised Land. The initial 42-acre property cost the media magnate roughly $50 million, and it had a 23,000-square-foot Georgian-style home, a 6,000-square-foot redwood guesthouse, and an outside space ideal for a pool, tennis court, and numerous patios. Winfrey still refers to this large estate as her primary residence and has continued to acquire surrounding properties over the years to increase her Montecito holdings.

Winfrey spent $298,000 on a much smaller four-bedroom Colonial-style house in the Elmwood Park neighbourhood, just outside of Chicago, that same year. The 2,250-square-foot house was mostly kept in its original condition by the television star, who invested some money in replacing the roof and gutters, the garage door, and the heating and conditioning system. She had no additional Chicago properties after it was ultimately sold in 2018 for $375,000.

Oprah Winfrey House


Winfrey spent around $5.3 million on two properties in Maui that combined for 163 acres. Both are made up of a number of buildings, but Winfrey lives in a grey ranch that she transformed with the aid of her interior designer friend Ellie Cullman into a warm modern farmhouse. The little restoration that started out as a full-scale project featured alterations like the installation of French doors, a higher ceiling in the master suite, and a wraparound porch ideal for admiring the views. A quilt-inspired stencil with patterned elements has also been added to the kitchen. Winfrey once gushed, “I love, love, adore my house.” It’s a treasure, very precious and lovely. Such a typical, everyday home. It has a cosy feeling. A beautiful and plush cashmere one.


When Winfrey paid $10.85 million for roughly 60 acres of land close to the Telluride Ski Resort in Colorado, she made headlines. She intended to construct a megamansion on the site, but she encountered a legal problem when a local retired nuclear physicist filed a lawsuit against her demanding trail access rights. The physicist told the Denver Post, “I don’t care if Oprah is a neighbour, but if she is going to cut off access to trails, I don’t find that appropriate. The lawsuit was ultimately dismissed, and it is unknown if Winfrey actually built her megamansion as planned.


The media tycoon increased her assets in Telluride the next year by investing another $14 million in a state-of-the-art residence there. Winfrey acquired the completely furnished five-bedroom, six-and-a-half-bathroom house from software entrepreneur Bob Wall. The building, which occupies 3.25 acres, is composed of stone, glass, and wood, and it contains a 56-foot-long underground wine cellar (also known as a wine cave), where sounds of creaking wood and trickling water are projected through speakers. Two other appealing features are a second 45-foot bridge that connects the house to a terrace located in the woods 35 feet above ground, as well as a tempered glass bridge with integrated fibre optic lighting that connects the main suite to a private office.

Two months later, Winfrey bought Seamair Farm, a long-established equestrian property nearby her original 42-acre Montecito residence, and started the gradual growth of her Promised Land ranch. The 23-acre home, one of the largest in the area, cost Winfrey $28.85 million. Cliff May, a Californian architect, created the main house, and it has a lot of outside features like a swimming pool, patio space, fish pond, fruit orchards, and two private wells. A training area, numerous stables, and a sizable circular paddock are among the estate’s equestrian amenities. A 44-acre dedicated preserve is ideal for growing a variety of crops.


In 2018, Winfrey decided to invest $8 million in two adjacent properties on Orcas Island, which is a part of the San Juan archipelago between Seattle and Vancouver. A main 7,303 square foot, four bedroom, five bathroom home and a smaller 2,948 square foot guesthouse, both constructed with rare salvaged timbers, made up the luxurious lakeside getaway, which covered an enormous 43 acres. The main house featured a floor-to-ceiling bookshelf-lined library, a double-height great room with a stone fireplace, and a kitchen with a built-in pizza oven. The Madroneagle complex has a sauna, an Asian garden, and a private beach on its property. Three years later, Winfrey ultimately decided to sell the home for $14 million, citing a lack of time as her rationale.

Oprah Winfrey House


Winfrey’s most recent real estate acquisition strengthens her steadily growing assets in Montecito. She increased her ranch’s size to an astounding 70 contiguous acres by paying actor Jeff Bridges $6.85 million for a four-acre structure. After the tragic 2017 mudslides, Bridges and his wife, Susan Geston, rebuilt the Spanish Revival-style property, creating a new aesthetic that incorporated the original 1919 detailing with more contemporary furnishings.

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