Oprah's Mansion: Insured?

With a net worth of $2.5 billion, it's no surprise that Oprah Winfrey has an extensive real estate portfolio. Her main residence is her Promised Land estate in Montecito, California, which she purchased for $50 million in 2001. The 42-acre property includes a 23,000-square-foot Georgian-style house, a guesthouse, a pool, and a tennis court. Over the years, Winfrey has expanded her Montecito compound by purchasing neighbouring properties, and it now spans 70 contiguous acres.

In addition to her main residence, Winfrey owns homes in Maui, Hawaii; Telluride, Colorado; Washington state; Chicago, Illinois; and Florida. She has also owned properties in Tennessee and Indiana, which she purchased for family and friends.

Oprah's main residence, 'The Promised Land' in Montecito, California

Oprah Winfrey's main residence is The Promised Land, a sprawling estate in Montecito, California. Winfrey, a billionaire media mogul, purchased the luxury home in 2001 and has since expanded the property by buying neighbouring plots to ensure her privacy.

The original 42-acre estate cost around $50 million and included a 23,000 sq. ft. Neo-Georgian style mansion, a 6,000 sq. ft. redwood guesthouse, and an outdoor area with a pool, tennis court, and multiple patios. Over the years, Winfrey has continued to snap up nearby properties, and by 2019, her compound had grown to a jaw-dropping 70 contiguous acres with 13 separate buildings.

The Promised Land boasts picturesque views of the Pacific Ocean and the Santa Ynez Mountains. It also features a 5,000 sq. ft. ranch-style house, a tea house, a koi pond, and various fruit and vegetable gardens.

Winfrey's partner, Stedman Graham, spends the most time with her at The Promised Land, which she has described as her "main home base".

Oprah's Maui mansion, a 21st-century farmhouse with ocean views

Oprah Winfrey's Maui mansion is a 21st-century farmhouse nestled in the idyllic Hana area. The house has a wraparound porch that appeals to her rural upbringing and provides gorgeous views of the ocean and surrounding property.

The Maui home was the result of a renovation project that transformed a small grey ranch with a cramped feel into a spacious and comfortable residence. Architectural designer Jeff Wooley, of John B. Murray Architect, rejigged the floor plan to create less angular rooms, and the house was stripped to its basic structure, with the staircase moved, the ceiling of the master bedroom raised, French doors installed throughout, and the entire house wrapped in a wide veranda.

Oprah's decorator, Ellie, furnished the rooms with extraordinary antiques that are part of American heritage, including a late-19th-century American weather vane in the shape of a galloping horse as the living room's centerpiece. The master bedroom has a high ceiling and opens directly onto the terrace, with sheer panels made from Belgian linen to catch the ocean breeze.

Oprah's Maui mansion is part of her portfolio of roughly 1,000 acres on the island, including 870 acres in Kula, an area southeast of Lahaina. In addition to her property in Maui, she also owns estates in Montecito, California; Orcas Island, Washington; Telluride, Colorado; Alpine, New Jersey; Florida; Chicago; and Nashville.

Oprah's Telluride, Colorado, home, with a high-tech wine cellar and private cable railway

Oprah Winfrey's $14 million home in Telluride, Colorado, is a high-tech ski paradise. The media mogul and billionaire purchased the 8,706-square-foot contemporary-style home from tech entrepreneur Bob Wall. The house has five plush bedrooms and 6.5 spa-like bathrooms, with a 7-person indoor hot tub and a $70,000 limestone tub programmed to regulate water temperature.

The house is packed with smart home features and high-tech gadgetry. It has a radiant heat system that keeps the driveway snow-free and driveway sensors that alert the homeowner when a car arrives. The previous owner, Bob Wall, could even water his indoor plants remotely via iPad.

The property boasts a 56-foot-long wine tunnel, which holds 1,600 bottles of wine. The wine cellar is designed to simulate an old historical mining tunnel, with water mists, sound effects, upcycled wood from a Utah railroad trestle, and faux stone walls. There is also a private steel funicular crafted to resemble an old mining car, which takes four people from the house to the Sundance Ski Run in just one minute. This amenity cost $240,000 to install.

The home also features a custom "etched and fiber-optic lighted glass bridge" that arches over the living room, connecting the master suite with the rest of the home. There are six view-maximizing decks, including a 35-foot-high stainless steel platform observation deck with a private fire pit and stunning views of the San Sophia Range.

Oprah's Washington State estate, Madroneagle, with a private beach and Asian garden

Oprah Winfrey, the American media tycoon, has an extensive real estate portfolio, with properties across the United States. One of her more recent acquisitions was Madroneagle, a 43-acre estate on Orcas Island, Washington. Winfrey bought the property in 2018 for $8.3 million and sold it in 2021 for $14 million.

Madroneagle is a gated island sanctuary with a main house, several other buildings, and a private beach. The main house has four bedrooms and five bathrooms, spanning over 10,200 square feet. The compound also includes a half-mile of waterfront and beach views, a greenhouse, an expansive shop, and a mother-in-law apartment.

The interior of the main house features rare reclaimed woodwork, heated floors, and premier kitchen appliances, including a wood-fired pizza oven. The estate also has an entertainment room, wine cellar, library, large office, sauna, and an Asian garden. The grounds are surrounded by nature trails, a pond, and a stream.

Winfrey sold Madroneagle because she was too busy to use the property, according to Wally Gudgell, an Orcas Island real estate broker. Despite selling the estate, Winfrey still owns several other properties across the country, including her main residence, the Promised Land, in Montecito, California.

Oprah's Chicago condo, which she sold for $4.625 million in 2015

Oprah Winfrey has had an extensive real estate portfolio over the years, owing to her success as a media mogul. One of her first big purchases was a condo in Chicago's Water Tower Place, which she slowly expanded by buying three other units surrounding the original one. Combined, the four units measured 9,625 square feet and featured four bedrooms, five full bathrooms, and two half bathrooms. Winfrey listed the enormous duplex for $7.75 million in January 2014 but ultimately sold it for $4.625 million in late 2015.

Winfrey's Chicago condo was not her primary residence, as she has spent more of her time at her estates in Montecito, California, and Hawaii. Over the years, she has slowly sold off her Chicago-area properties, including her Harpo Studios campus on the Near West Side and a retail condo that once held her Oprah Store. In 2012, she also took a significant loss on the sale of a co-op unit in Streeterville, which she bought for $5.6 million in 2006 but sold for less than half that price in 2012.

By 2015, Winfrey had severed most of her real estate ties to Chicago, though she continued to own several small properties in the area, including a house in Elmwood Park and another in Merrillville, Indiana.

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