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    Inside Oprah Winfrey’s $150 Million Property Portfolio

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    Few names carry the weight—and warmth—of Oprah Winfrey. With a net worth of $3.1 billion, the 71-year-old media mogul has built an empire that reaches far beyond her groundbreaking talk show. Since rising to fame in the late ’80s, she’s launched the OWN network, invested in WeightWatchers, and inked a headline-making content deal with Apple TV+ that ran through 2022, producing everything from documentaries to her beloved book club.

    Much of that fortune stems from savvy reinvestments: profits from The Oprah Winfrey Show and films like The Color Purple, Beloved, and Selma—all co-produced by her Harpo Productions—have reportedly generated more than $2.5 billion to date.

    Winfrey, who became the first Black woman to appear on Forbes’ billionaire list in 2003, has cultivated a lifestyle as expansive as her influence. Her Gulfstream G650 is one marker of that scale, but it’s her real estate portfolio that offers the clearest window into how and where she chooses to live.

    While Montecito remains her primary base—anchored by her famed Promised Land estate—Winfrey has owned properties across the country, from Hawaii to Colorado. Some have remained in her orbit for decades; others she’s flipped, gifted, or sold for a significant profit. In Chicago, where The Oprah Winfrey Show was taped from 1986 to 2011, she quietly offloaded several holdings, including a 9,600-square-foot condo and multiple units in a historic loft building. In Georgia, she sold a luxe Atlanta penthouse and gifted a five-bedroom home in Douglasville to a friend. And in 2021, she sold her striking 40-acre Orcas Island compound—dubbed Madroneagle—in a discreet $14 million deal after purchasing it at a steep discount just a few years earlier.

    Even in Montecito, she’s made calculated moves. In 2021, she split a $10.8 million estate into parcels, later selling the main farmhouse to Friends star Jennifer Aniston for $14.8 million, while the smaller cottages went to her longtime friend and personal trainer Bob Greene.

    Winfrey has often said she seeks out homes that inspire and elevate—and her real estate portfolio proves she’s done exactly that. Based on what she’s paid, her holdings total over $120 million. But when you factor in appreciation and upgrades—especially in places like Montecito and Maui—that number could easily be north of $150 million today. Below, a closer look at the standout properties in her extraordinary collection.

    Promised Land  

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      Home of the Week: This $39 Million Hawaiian Compound Has 4 Homes and 150 Feet of Pristine Coastline

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      This grand Hawaiian estate on Maui was certainly designed for entertaining.

      The sprawling property, located along a spectacular stretch of coastline, had long been owned by Jerry Moss, the late record producer and co-founder of A&M Records. Moss, who passed away in August 2023 at the age of 88, acquired the first part of the compound in 1995 for $2.5 million, according to the WSJ. In 2000, he purchased an adjoining parcel and later acquired another. Together, he amassed 1.4 acres. During this time, Old Makena Road was known for its rustic dirt lanes and secluded beaches. Today, the area has several mansions and beachfront properties.

      The open-plan living areas spread out over multiple levels.

      Travis Rowan

      On the market for $39 million, it’s currently the most expensive active listing in the state of Hawaii. The gated property has 148 feet of beach frontage along Po’olenalena Beach and comprises four houses, which Moss and his family built over the years. Together, there are a collective seven bedrooms and seven bathrooms in 6,352 square feet of living space. Unlike many modern-day multi-million-dollar Hawaiian compounds, the four residences are all modest in size, and each bungalow boasts an intimate vibe and indoor-outdoor living.

      Moss and his wife, Tina, whom he married in 2019, replaced the wood siding of the four homes with smooth stucco and weather-resistant ipe wood. Inside, the homes feature teak detailing and local materials, such as the stone fireplace in the main residence. Throughout the homes, there is quintessential island-style decor, like wooden paddles, tiki heads, surfboards, and ukuleles hanging along the walls.

      The covered lanai of the main residence has a particularly appealing view.

      Travis Rowan

      The main residence features an open, airy layout with vaulted, wood-beamed ceilings. There is a chef’s kitchen with top-of-the-line appliances and a nearby large dining area. Down a few steps is the cozy living room with panoramic windows and perfectly framed views of the beach and Pacific Ocean. Sliding glass pocket doors open to the covered lanai with a fire pit. Upstairs is the home’s primary bedroom, which connects to a covered terrace.

      There’s also an outdoor kitchen with a barbecue off to the side of the home and a nearby outdoor dining table. A manicured lawn, sprinkled with tropical foliage and swaying palm trees, is the only thing that separates the house from a pristine stretch of beach. The lawn features sun loungers and a hammock to enjoy the postcard views on breezy Hawaiian afternoons.

      The homes are clustered together. However, each is surrounded by lush landscaping that gives it a sense of privacy. Bright flowers and native plants line the walkway between the homes. The property also features a large swimming pool with stunning ocean views, as well as an outdoor lava rock shower with a bright mosaic wall. Tiki torches illuminate the grounds at night.

      The pool overlooking the ocean.

      Travis Rowan

      According to the WSJ, Moss and his family moved to Hawaii full-time during the COVID pandemic; the family has decided to sell and create new memories elsewhere. The property is co-listed by Nancy Callahan of Coldwell Banker Island Properties and Paul Stukin of Deep Blue HI. 

      Moss, who founded A&M Records alongside Herb Alpert, oversaw an impressive roster of musicians, including Liza Minelli, Sting, Janet Jackson, Carole King, and many others. Shortly after the music industry mandarin died last year, the family also listed a Bel-Air mansion for $53 million. The home was built in 1937 and has five bedrooms and 13 bathrooms.

      Click here for more photos of 4610 Makena Road. More

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      in Luxury

      Kris Kristofferson’s Sprawling Northern California Ranch Hits the Market for $17.2 Million

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      Country superstar Kris Kristofferson has placed his Northern California ranch of almost 40 years on the market. Nestled on 557 lush acres outside of Elk, about three hours north of San Francisco, the retired singer-songwriter recently listed the sprawling oceanfront compound for a cool $17.2 million, The Wall Street Journal first reported.

      Kristofferson originally bought the ranch in 1980 and, over the decades since, has leased a good chunk of the land for cattle grazing, which shouldn’t really come as a surprise. He is a Texas native, after all.

      Kris Kristofferson put his Northern California ranch up for sale

      Anthony Wells/Mendo Sotheby’s International Realty

      “The ranch has always been a place of creativity and inspiration,” the A Star Is Born actor told the newspaper. Dating back to the 1800s, the legacy ranch began as a dairy farm and still includes some of the original structures. In addition to the 2,400-square-foot barn that Kristofferson and his wife used as a vacation house, there is also a 1,900-square-foot ranch house, a dairy barn, and a feed barn, all of which are in need of a little TLC.

      Listed for $17.2 million, the compound includes original buildings from its beginnings as a dairy farm

      Anthony Wells/Mendo Sotheby’s International Realty

      As it stands, the property features 300 acres of open pasture and approximately 250 acres of forestland that are dotted with old-growth redwood and fir trees. Offering up a mile of Pacific Ocean frontage, the property sits right below Devils Basin. Given the scale and location, there’s a possibility that the land could be subdivided or even expanded upon. “I grew up here, and this property, in a lot of ways, is steeped in history,” Justin Nadeau of Mendo Sotheby’s International Realty told the WSJ. “Nobody has seen a property like this one come to market.”

      The property measures over 550 acres

      Anthony Wells/Mendo Sotheby’s International Realty

      Kristofferson and his wife still own another home in Hawaii, on Maui, which has become their main residence. As for the ranch, Nadeau added at the time of the listing that the couple feels like “it’s time to let it go and move on.” 

      Click here to see all the photos of The Kristofferson Ranch. 

      Anthony Wells/Mendo Sotheby’s International Realty More