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Hedge fund billionaire Ken Griffin is well known for snapping up real estate in jaw-dropping and record-setting deals. Among his most notable acquisitions is a Manhattan penthouse that set a national price record and, because his holdings go far beyond that one landmark purchase, solidified his place among the top buyers of eight- and nine-figure […] More
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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Published on July 4, 2025
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Call it the new celebrity arms race—not for Birkins or Labubus, but for architectural trophies signed by the likes of Frank Lloyd Wright, Richard Neutra, and John Lautner. For today’s ultra-wealthy, owning a name-brand house is the ultimate flex. From Malibu to Montecito, these homes aren’t just places to live—they’re cultural capital, conversation starters, and investment-grade icons.
The limited number of well-preserved homes by A-list architects does make them a needle in a haystack when hunting for a home, but due to the care and resources required to restore and update these types of structures, their pool of potential buyers can be somewhat limited to those with a dedicated penchant and a deep pocketbook for one-of-a-kind labors of love and frequent maintenance. And in a market where scarcity drives desire, architectural provenance is becoming just as valuable as ocean views or square footage.
Look at Beyoncé and Jay-Z, who shattered California’s real estate record in 2023 with their $200 million all-cash throwdown for a minimalist fortress in Malibu by the Japanese master Tadao Ando, originally built for art collectors William and Maria Bell. Floating above the Pacific, the concrete house cemented Ando’s status as architecture-world royalty. Rapper Kanye West grabbed another Ando home in Malibu back in 2021 for $57.3 million. Much to the surprise of many, he gutted it, then listed the unfinished shell for $53 million. It eventually sold for just $21 million to a crowdfunding real estate development concern, who quickly flipped it to property developer Andrew Mazzella for more than $30 million.
Kanye West bought a Tadao Ando home in Malibu, gutted it, then sold the unfinished property at a huge loss.
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West’s ex-wife, Kim Kardashian—whose Axel Vervoordt–designed home in the L.A. suburb of Hidden Hills helped launch the creamy, monastic minimalism movement in interior design—is said to be building her own Ando–designed escape near Palm Springs. Designer and filmmaker Tom Ford, meanwhile, commissioned Ando to build an austere, geometric masterpiece on his sprawling Cerro Pelon Ranch in New Mexico. Ford first listed the property in 2016 for $75 million, later dropping the price to $48 million in 2019 before it quietly sold to an undisclosed buyer in 2021.
Then there’s Austrian-American innovator Richard Neutra, who draws a cult-like following. His iconic Brown House in L.A.’s Bel Air neighborhood passed from the hands of Ford (who owned it for nearly 20 years) to Ellen DeGeneres and Portia de Rossi, and finally, writer-producer Ryan Murphy, who scooped it up for $29 million in 2022. The six-time Emmy-winning TV producer gave it a glow-up, had it showcased on Architectural Digest, and recently relisted it for $34 million. DeGeneres and de Rossi, serial buyers and sellers of pedigreed real estate, have also owned homes by A. Quincy Jones, Wallace Frost, and Hal Levitt.
Richard Neutra’s Brown House in Bel Air has passed through the hands of Tom Ford, Ellen DeGeneres, and Ryan Murphy.
Matthew Momberger
John Lautner homes are another favorite among the entertainment industry elite. After buying the oceanfront Stevens House in the guard-gated Malibu Colony, Edward Norton sold a much more classically beachy bungalow on Las Flores Beach to Benny Blanco. Back when Courteney Cox and David Arquette were still married, they owned a tour-de-force Lautner on Carbon Beach, which was later sold to the one-time owner of the L.A. Dodgers, Frank McCourt, for $33.5 million.
Four decades after entertainer Bob and Dolores Hope commissioned Lautner to build what would become one of his most iconic and unconventional works, the Bob Hope House in Palm Springs is currently undergoing a meticulous restoration to bring the 24,000-square-foot spaceship-like residence back in line with the architect’s original vision.
In the ’70s, Bob Hope commissioned John Lautner to build a mountaintop opus in Palm Springs.
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Few architects have a résumé that spans both A-list ownership and starring roles on screen, but Lautner’s legacy certainly isn’t confined to real life. On Apple TV’s The Studio, Seth Rogen’s character lives in the Foster Carling House in the Hollywood Hills, while Patty Keigh, played by Catherine O’Hara, inhabits the Harvey House, long owned by actress Kelly Lynch and her husband, writer-producer Mitch Glazer, who famously outbid Leonardo DiCaprio for the hilltop spread.
And of course, there’s Frank Lloyd Wright—the original starchitect. His 1924 Ennis House in Los Angeles, with its Mayan Revival façade and Blade Runner cameo, was restored by billionaire investor Ron Burkle, who sold it for $18 million in 2019. (Burkle currently owns the aforementioned Bob Hope residence in Palm Springs.) That same year, fashion designer Marc Jacobs scooped up Wright’s Max Hoffman House in Rye, New York, for just over $9 million. The waterfront Usonian-style abode was lovingly restored over four years, in collaboration with the Frank Lloyd Wright Building Conservancy.
Frank Lloyd Wright’s Ennis House still draw major buyers, including billionaire Ron Burkle.
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Long a getaway for elite sun seekers and a proving ground for maverick architects, Palm Springs and the surrounding communities have become a sandbox for provenance collectors. Oscar winner Leonardo DiCaprio owns a 1964 house by midcentury master Donald Wexler that was originally built for singer Dinah Shore; he now rents the restored and updated home as a luxe retreat.
Back in L.A., Denzel Washington once lived in a Toluca Lake home designed by the acclaimed Paul R. Williams that had previously been owned by Bill “Bojangles” Robinson. Williams famously counted a slew of high-caliber clients like Frank Sinatra, Cary Grant, and Lucille Ball as clients; Jay Paley, a founder of CBS, commissioned a Williams-designed mansion in Bel Air that was later owned by the late hotelier Barron Hilton and is now owned by former Google exec Eric Schmidt.
Diane Keaton is also a well-known aficionado of homes by esteemed architects, having restored multiple architecturally significant and historic homes across L.A., including a Spanish Colonial Revival by Lloyd Wright (Frank’s son). And Brad Pitt, forever the design obsessive, once tapped Frank Gehry for a custom build and currently owns a glass-walled pavilion in the Hollywood Hills by Case Study architect and educator Craig Ellwood.
The truth is, at the highest levels of wealth and luxury, owning something beautiful isn’t enough. You want something authored. And a signature on the blueprints? That has become one of the world’s ultimate status symbols.
Authors
Abby Montanez
Abigail Montanez is a staff writer at Robb Report. She has worked in both print and digital publishing for over half a decade, covering everything from real estate, entertainment, dining, travel to…
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Among Silicon Valley’s elite, Eric Schmidt stands out not only as a visionary tech leader but also as a prolific real estate collector, acquiring multiple high-profile properties—even several within the same month. While not all holdings are publicly listed, his portfolio is estimated to be worth half a billion dollars or more. Schmidt previously served […] More
David and Victoria Beckham don’t just rule the worlds of soccer and fashion—they’ve built a global empire that extends far beyond the pitch and the runway. And their choices in residences, spanning sleek city penthouses, countryside estates, and waterfront mansions, each reflect their signature blend of style and star power. Whether basking in the Miami sun, retreating to the English countryside, or laying low atop Dubai’s tallest tower, the Beckhams know how to live iconically.
In addition to their primary professions, they’ve each cultivated powerhouse brands. David’s ventures include co-owning Inter Miami CF, launching grooming and whiskey lines, and founding Studio 99, the production company behind the Emmy-winning 2023 Netflix doc Beckham. Victoria, meanwhile, turned her Spice Girls superstardom into a thriving fashion and beauty label, Victoria Beckham Holdings Limited. Together, their combined net worth is estimated at £500 million (about $671 million), according to The Sunday Times Rich List.
Their homes have tracked their rise. In Spain, during David’s Real Madrid era, they owned a Tuscan-style villa ideal for their growing family. When he joined LA Galaxy in 2007, the Beckhams settled into a 13,000-square-foot Beverly Hills mansion with six bedrooms, nine bathrooms, and a custom media room for Victoria. They sold it quietly for $33 million in 2018, closing a glitzy, tabloid-tracked chapter in Lala Land.
Even at sea, the Beckhams do it big. Their $20 million Riva 130 Bellissima yacht, Seven—named for David’s squad number, which is also daughter Harper’s middle name—is a floating retreat, not only for the two of them but also for their four kids, Brooklyn, Romeo, Cruz, and Harper.
Now, let’s take a closer look at their impressive collection of homes.
Burj Khalifa Condo
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Published on June 13, 2025
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Published on June 10, 2025
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Justin Bieber has come a long way since his headline-making days of rental-hopping and wild party pads. The 31-year-old pop phenom first rose to fame in 2009 with his breakout EP My World and the hit single “Baby,” building his fortune through music tours, record sales, brand deals, and his Drew House clothing line. Now married to […] More
