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    Inside Justin and Hailey Bieber’s $29,000 Vacation Rental in Mallorca

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    Justin Bieber may have just released a new album, but that doesn’t mean he’s too busy to take a vacation.

    Last week, the Canadian pop superstar and his wife, Hailey, jetted off to Mallorca, where they shacked up in a lavish villa that goes for an average overall rate of 25,000 euros, or just under $29,000. The six-bedroom, six-bath spread is nested into the steep, rocky hillside above the picturesque cove Cala Llamp, with sea views from just about every room. Available via Vrbo, now you can make like the Biebers and stay in the home on your next European getaway.

    The breezy and comfortable, neutral-toned living room includes a fireplace and a bar.

    Vrbo

    Built in 2014, the villa spans more than 10,000 square feet across three levels. The entry hall leads into neutral-toned entertaining spaces. The modern main kitchen is accompanied by an additional utility room/prep kitchen; the airy living room is warmed up by a fireplace and includes a bar for pre- or post-dinner drinks; and the dining room table is surrounded by emerald-green chairs for a splash of rich color that mimics the gardens just outside.

    All six bedrooms come with a private bathroom, ensuring each guest discreet privacy. Additional highlights range from a wine cellar to a sea-view fitness room, meaning that you can look out on the Mediterranean while you run on the treadmill or ride the stationary bike. And, when you’re ready for a bit of relaxation, the spa area includes a sauna for sweating out the toxins and soothing tired muscles.

    The 50-foot pool bleeds into the mountainous horizon.

    Vrbo

    On the covered patio, there’s an outdoor kitchen and built-in barbecue with an adjacent table for alfresco meals. The lounge area is heated up by a gas fireplace, and you can cool down in the 50-foot zero-edge swimming pool.

    While the Beverly Hills-based Biebers seem to enjoy vacationing on the other side of the Atlantic, they don’t yet own any homes on the continent. The couple’s portfolio isn’t anything to scoff at, though. The $47 million dollar collection of homes includes a lakefront estate in Ontario, Canada, about an hour from where Justin grew up; a $25.8 million primary residence in L.A.’s guard-gated Beverly Park enclave; and a $16.6 million manse in the celeb-favored Madison Club golf community in La Quinta, California.

    Click here to see all the photos of the ocean-facing vacation rental.

    Vrbo

    Authors

    Tori Latham

    Tori Latham is a digital staff writer at Robb Report. She was previously a copy editor at The Atlantic, and has written for publications including The Cut and The Hollywood Reporter. When not…

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      An Oscar-Winning Art Director Just Listed His 1920s L.A. Home for $4.8 Million

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      It’s officially a wrap for Rick Heinrichs, who has decided to part ways with his Los Angeles home in a prime enclave of Brentwood after a little more than two decades of ownership.

      The acclaimed production designer and art director—best known for partnering with Tim Burton on films such as The Nightmare Before Christmas, Edward Scissorhands, Batman Returns, and Sleepy Hollow, for which he won an Oscar—is asking $4.75 million for the Spanish-style spread he and his wife Dawn originally acquired in 2002 for $2 million. Lauren Ravitz of Berkshire Hathaway HomeServices California Properties and Shelton Wilder of Christie’s International Real Estate share the listing.

      Large windows in almost every room bathe the home in natural light.

      Neue Focus

      RELATED: L.A.’s Famed 112-Acre Robert Taylor Ranch Is Back on the Market for $70 Million

      The stucco and terracotta-roof structure, perched atop a two-parcel knoll spanning nearly half an acre, was built in the late 1920s and offers five bedrooms and six baths in roughly 4,500 square feet. The historic yet modernized living spaces span three levels and boast a mix of hardwood and tile floors, vaulted wood-beam ceilings, plaster walls, glass doorknobs, vintage light fixtures, and interior doors crafted from solid wood.

      Steps lead up to a centrally based turret, where the front door opens into an entry foyer that flows to a sunken living room sporting a hand-crafted stone fireplace, built-in shelving, and large casement windows overlooking the treetops stationed on both sides. Other highlights include a coffered-ceiling dining room, which connects to an updated kitchen featuring quartz countertops, custom glass-front cabinetry, top-tier stainless appliances, a breakfast nook, and access to an ocean-view front deck that’s ideal for alfresco dining.

      A lower-level media room is clad in rustic wood paneling.

      Neue Focus

      RELATED: A Perfectly Preserved 1960 Richard Neutra Masterpiece in L.A. Hits the Market for $8 Million

      Three upstairs bedrooms include a spacious primary suite, which has a separate sitting area and a spa-like bath within the turret that’s decked out with dual vanities, a clawfoot soaking tub, and a glass-encased shower. Two more bedrooms downstairs have doors spilling out to a courtyard, while a wood-paneled media room anchors the lower level.

      Rounding it all out are the fully hedged grounds, which offer several spots ideal for lounging and entertaining amid a fire pit, mature trees, and a rolling grassy lawn. There’s also a detached three-car garage sitting street side, plus additional parking for up to eight vehicles.

      The Heinrichs have decided to sell because they have been working on and off in the U.K. since 1998 and are now relocating there full time. “Daily sunsets, wonderful breezes, and especially the annual fireworks show are just a few reasons why it is difficult to sell,” says Dawn Heinrichs. “We raised our kids here and loved watching them play in the backyard, which has plenty of hiding places and room to run.”

      Click here for more photos of the Brentwood residence.

      Neue Focus

      Authors

      Wendy Bowman

      Wendy Bowman is a real estate writer at Robb Report. Before that, she was a freelancer for Modern Luxury and several other media outlets, where she primarily covered luxury properties for…

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      Former NBA Star Tony Parker’s $16.5 Million Texas Mansion Includes a Waterpark With 8 Pools

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      After first listing his Texas Hill Country home in late 2021 for $19.5 million, retired NBA star Tony Parker is officially doubling down on efforts to sell the sprawling property he’s owned for around two decades, this time with a new real estate agent and a marketing plan featuring a popular internet personality.

      The six-time All-Star and former San Antonio Spurs point guard—he currently spends most of his time across the pond, where he’s the majority owner and president of the French pro basketball team LDLC ASVEL—has just put his Mediterranean-style residence tucked away in the suburban community of Boerne, some 25 miles northwest of San Antonio, back on the market after a brief absence for $16.5 million.

      The main home has six bedrooms, five full baths, and four half-baths in about 13,300 square feet.

      The listing is now held by Erwin Nicholas II of Houston-based Mr. Real Estate, and he’s brought Twitch entertainer Kai Cenat and his AMP (Any Means Possible) crew on board to help advertise the extravagant 53-acre spread to their millions of viewers during the month of July. The 30-day live streamathon features a pop-up Nando’s peri-peri restaurant, plus a look at more permanent perks like a nearly 6,000-square-foot gym with a half-court basketball setup and an arcade, a wet bar-equipped movie theater, a barber studio, dual offices, a 1,500-bottle wine cellar, a fingerprint-access trophy room, and an over-the-top waterpark.

      “This isn’t just a home—it’s a legacy,” Nicholas told Robb Report. “Tony Parker’s estate blends world-class amenities with a sense of wonder no other property in Texas can offer. From the tallest private water slides to the largest residential waterpark in the country, we’ve created a cultural moment that merges luxury real estate with generational storytelling.

      “Live streaming has proven to be a powerful emerging market that delivers unprecedented viewership while bringing families together in real time,” he added. “It’s the best global open house you can have—and this estate is the perfect stage.”

      A half-court basketball setup is lined with a collection of life-sized Marvel and DC characters.

      Leonardo Lopes

      Custom-built on a multi-lot parcel the NBA Hall of Famer purchased in 2005, the 53-acre compound within the exclusive Anaqua Springs Ranch community was completed in 2009 while he was still married to actress Eva Longoria. Securely hidden away behind double gates with a guardhouse and a Jurassic Park-themed rear entrance, the residence includes a main mansion, a separate guesthouse, and a detached gym—for a combined total of 10 bedrooms and 12 baths spread across roughly 21,200 square feet.

      Inside the primary dwelling, a sweeping wrought iron-railed staircase and an elevator flow to bi-level living space anchored by a double-height living room sporting a stone fireplace and floor-to-ceiling windows. From there, a formal dining room seats 16 and a vaulted family room connects to a light gray-hued kitchen outfitted with an eat-in island and top-notch stainless appliances, while an opulent primary suite sports a lounge, a massive walk-in closet, and a marble and travertine bath.

      The waterpark was created by one of the original builders of the waterpark at Six Flags Fiesta Texas in San Antonio.

      Leonardo Lopes

      Rounding it all out are the resort-inspired grounds, which host tennis and sand volleyball courts, a full outdoor kitchen with a pizza oven, a greenhouse, an herb garden, a fruit orchard, and even a tortoise habitat. There’s also the professionally crafted waterpark, which includes eight pools, a mountain, grottos, several slides, a 35-foot-high jumping ledge, a trio of hot tubs, water cannons, and a lazy river.

      The Spurs legend and four-time NBA champion earned almost $170 million over his 18-year career before retiring in 2019 after a final season with the Charlotte Hornets. In addition to his Texas estate, the 43-year-old Belgium native also maintains a historic chateau in France’s southern Rhône Valley, where he operates a vineyard.

      Click here for more photos of the San Antonio-area residence.

      Leonardo Lopes

      Authors

      Wendy Bowman

      Wendy Bowman is a real estate writer at Robb Report. Before that, she was a freelancer for Modern Luxury and several other media outlets, where she primarily covered luxury properties for…

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      L.A.’s Famed 112-Acre Robert Taylor Ranch Is Back on the Market for $70 Million

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      A sprawling Los Angeles ranch property long owned by the late film and TV actor Robert Taylor has just hit the market for the first time in a decade. Nestled into the Mandeville Canyon neighborhood of Brentwood, just minutes from the popular Country Mart and Rodeo Drive, the entire spread is asking a cool $70 million, with the listing held by Rochelle Maize of Nourmand & Associates.

      Originally designed and built in the 1950s by noted architect Robert Byrd for petroleum magnate Waite Phillips, the estate was subsequently acquired by Taylor, who lived there until his death from lung cancer in 1969 at age 57. Married throughout the ’40s to screen legend Barbara Stanwyck, the Hollywood Walk of Fame inductee starred in the iconic early 1950s films Quo Vadis and Ivanhoe and later appeared in the TV series The Detectives and hosted the series Death Valley Days.

      A rustic-chic living area has collapsible steel-framed glass doors opening to the pool area.

      Anthony Barcelo/Barcelo Photography Inc.

      RELATED: Designer Windsor Smith Left Her Signature Mark on This $19.5 Million Estate in L.A.

      The residence was purchased in the 1970s for just $900,000 by the late radio concert promoter and radio station magnate Ken Roberts, who wound up relinquishing it to the financial services firm New Stream Capital in 2010 to settle a $27.5 million legal claim. New Stream immediately put it back up for sale at nearly $30 million. After reducing the price and having no takers, however, the place ultimately sold at auction for $12 million to Chicago-based real estate developer Fred Latsko. It last traded hands in late 2015 for $18.7 million and has since been extensively renovated by designer Malcolm James Kutner.

      Fully fenced and gated, the property features a main home and multiple guest and staff quarters spread across roughly 20,000 square feet. Special amenities include a casino lounge, a gym, meditation and massage rooms, a dog spa, an art studio, and a children’s playhouse, just for starters.

      The fully renovated barn includes up to 12 horse stalls, a tack room, and a stable manager’s office.

      Anthony Barcelo/Barcelo Photography Inc.

      RELATED: Gwyneth Paltrow’s Los Angeles Home Just Sold for $22 Million

      Inside the 12,000-square-foot primary dwelling are formal living and dining rooms, along with a library and a media room. A gourmet kitchen is outfitted with Wolf appliances and an accompanying breakfast nook, while five to seven bedrooms (depending on the configuration) include a fireside primary suite boasting a custom walk-in closet, a steam shower, and a sauna.

      Rounding it all out are the expansive grounds, which are showcased by a rock-encased pool and spillover spa, a fire pit conversation area, an outdoor kitchen with a grill and a pizza oven, equestrian facilities, hiking trails, a private well, and parking for around 20 vehicles. There’s also a generator, plus advanced fire-safety systems.

      Click here for more photos of the Brentwood residence.

      Anthony Barcelo/Barcelo Photography Inc.

      Authors

      Wendy Bowman

      Wendy Bowman is a real estate writer at Robb Report. Before that, she was a freelancer for Modern Luxury and several other media outlets, where she primarily covered luxury properties for…

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      The Creator of ‘Arthur’ Just Listed His Storybook Mansion in Martha’s Vineyard for $6.9 Million

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      If you grew up watching the animated sitcom Arthur or reading the beloved books, get ready to experience a little nostalgia in real estate form. The longtime Martha’s Vineyard home of Arthur creator Marc Brown and his wife, artist and author Laurene Krasny Brown, is up for grabs for the first time in 37 years. Asking price? $6.9 million.

      Tucked inside Pilot Hill Farm—a tightly held enclave known for its privacy, farm access, and walkable beach—the nearly eight-acre compound feels like something out of a picture book. Fitting, given who lived here.

      The heart of the property is a historic farmhouse that was built in 1730 but has been lovingly restored over the years. It showcases a myriad of delightful original features, such as hand-painted Siberian elm floors, cozy fireplaces, gunstock posts, and a classic Dutch door. There’s no shortage of modern touches, either: A sprawling great room, a screened-in porch overlooking a saltwater pool, and a bright, updated kitchen make the home as functional as it is charming.

      RELATED: A Dr. Seuss Collaborator’s Former N.Y.C. Townhouse Can Be Yours for $13.5 Million

      Wildflower meadows, stone walls, and a tranquil pond create an enchanting backyard.

      Marc Fairstein/ozoroco

      Spread out across the grounds are a handful of equally enchanting outbuildings: an artist’s studio, a three-car carriage house with a second studio upstairs, and a guesthouse with two more bedrooms and a soaring double-height living room.

      As both author and illustrator, Brown has long drawn inspiration from the world around him. The aardvark’s bedroom in Arthur was loosely based on his own son’s childhood room in Hingham, Massachusetts, The Wall Street Journal reported. And in his most recent animated series Hop on HBO Max, a moss-covered stone bridge on this very Vineyard property sparked the idea for a hidden troll’s home, tucked away in the woods. Outside, it’s all wildflower meadows, stone walls, and shady trees—plus a pond, a babbling brook, and gardens that feel more like a private arboretum than a backyard. Like much of Brown’s storytelling, the landscape here lives somewhere between reality and imagination.

      RELATED: Former Celtics Co-Owner Jim Pallotta Lists His Sprawling Massachusetts Estate for $38 Million

      The property has not one but two artist studios.

      Danielle Mulcahy/Tea Lane Associates

      “This is a natural haven in a magical setting,” notes the listing, which is represented by Alexis Holden and Elle Lash of Tea Lane Associates/Forbes Global Properties. For fans of Arthur—or anyone craving an island retreat with history, heart, and serious creative pedigree—this storybook sanctuary might just be the perfect next chapter.

      That said, it arrives amid a wave of high-profile activity on the Vineyard. In May, the Obamas’ former summer rental—now owned by famed architect Norman Foster—returned to the market with a $39 million price tag. Set on 30 acres in Chilmark, the estate blends presidential history with contemporary design, having undergone an extensive renovation after Foster purchased it in 2011. And last year, Diane Sawyer’s waterfront compound in nearby Tisbury sold for $23.9 million after just two months on the market. Best get in quick if you want Brown’s pad.

      Click here to see more photos of Marc Brown’s Martha’s Vineyard home.

      Marc Fairstein/ozoroco

      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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      Fashion Designer Richard Tyler’s Dapper Pasadena Villa Can Now Be Yours for $12.5 Million

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      An Italian Renaissance Revival villa in Pasadena, California, has a storied history befitting its spectacular appearance.

      Envisioned more than a century ago by the architect Reginald Davis Johnson, the $12.5 million abode is being brought to market by Australian fashion designer Richard Tyler and his wife, Lisa Trafficante. Tyler acquired the property back in 1998, but instead of buying the Pasadena estate in a traditional sense, he traded a mansion in the Hollywood Hills for it. Prior to Tyler and Trafficante making the grand residence their home, it had a suite of important owners, including the chemist and scholar Arno Behr, whose wife named the property “Villa Arno” in his honor. George Penner at Compass and Michelle Trafficante at Ashby & Graff now hold the listing.

      The minty-green fireside library’s arched windows and doors open to the gardens.

      Sterling Reed Photography

      Sitting on about an acre, the estate encompasses a five-bedroom, five-bath main residence and a one-bedroom, one-bath guest house. A classic black-and-white tiled floor lines the entrance gallery, which opens to the spare formal living room and the more eccentrically appointed library, both with fireplaces. While many of the rooms have an Old World atmosphere, thanks to the original Palladian doors, soaring ceilings, and period woods, the kitchen strikes a contrasting note. The modern space includes stainless-steel appliances and sleek white cabinetry, with a butcher’s block island smack-dab in the center.

      The primary suite is upstairs, where the bedroom is accompanied by both a dressing room and a sunroom, plus a walk-through closet and bathroom. Two more ensuite bedrooms are found up here, with two more bedrooms downstairs on the ground floor. The private guest house is a fully livable space with a kitchen and a fireplace-warmed living room.

      The primary suite includes a fireplace, a dressing room, and a sunroom.

      Sterling Reed Photography

      Outside, the pool setup adds to the Italian ambience. The swimmer’s pool is surrounded by beach loungers and cabanas, from which you can imagine you’re on the Riviera. The outdoor dining area is equipped with a grill and a fireplace, while the landscaping includes a hidden rose garden and calming water features.

      Villa Arno was initially conceived as the winter home of a New York doctor, who sold it to Behr before the property could be finished. Subsequent owners included a 1930s interior designer, the onetime president of the Southern California Gas Company, and the artist Earle Hugens. Thanks to both this ownership history and the home’s architectural legacy, it was honored as a Cultural Heritage Landmark back in 1977, and it has the potential to be added to the California Register of Historical Resources and the National Register of Historic Places.

      Click here to see all the photos of the Pasadena estate.

      Sterling Reed Photography

      Authors

      Tori Latham

      Tori Latham is a digital staff writer at Robb Report. She was previously a copy editor at The Atlantic, and has written for publications including The Cut and The Hollywood Reporter. When not…

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      A Cleveland Browns Scion’s 6-Story Manhattan Townhouse Lists for $20 Million

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      Almost four years ago, James Haslam doled out $12.5 million for a historic townhouse in Manhattan’s Chelsea neighborhood. The filmmaker and co-owner of the David Armstrong Archive subsequently enlisted the services of friend and interior designer Amy Kolker of Jane Street Projects, and together they embarked upon an extensive renovation of the formerly white-walled residence that was recently featured in Architectural Digest.

      Halsam, whose parents, Jimmy and Dee Haslam of Haslam Sports Group, co-own the NFL’s Cleveland Browns and the NBA’s Milwaukee Bucks, has now decided to put the strikingly transformed digs on the market for a speck under $20 million. Matthew Slosar and Justin Grabell of Douglas Elliman hold the listing.

      An entertainment-ready living room with a brass-topped bar spans two levels.

      Evan Joseph/Evan Joseph Studios

      RELATED: A Dr. Seuss Collaborator’s Former N.Y.C. Townhouse Can Be Yours for $13.5 Million

      When coming up with a design plan, Kolker and Haslam gleaned their inspiration from a set of very specific people and places—the modern steel-and-glass Maison de Verre residence in Paris dating to the 1930s; Austro-Hungarian architect Adolf Loos, known for his minimalist yet luxe spaces; filmmaker David Lynch and his penchant for stark surrealism; and Italian design master Lorenzo Mongiardino‘s poetic maximalism. The result? A conglomeration of plush, moody interiors that evoke an old-world ambience, set sometime between the 1930s and 1970s.

      Standing out in the five-bedroom, eight-bath spread, which clocks in at 22 feet wide and 7,500 square feet across six levels, is a double-height living room boasting terracotta pavers sealed in a glossy black epoxy, a wet bar, and floor-to-ceiling industrial windows trimmed in a deep red shade. Soft, sheer ivory curtains open to reveal a bamboo garden inspired by Halston’s house on the Upper East Side.

      The eat-in kitchen is lined with fluted emerald tiles.

      Evan Joseph/Evan Joseph Studios

      RELATED: Art Dealer Barbara Gladstone’s Elegant Manhattan Row House Lists for $12 Million

      Other highlights include an office and a dining room/library, as well as an emerald-tiled kitchen outfitted with veined-marble countertops, custom brass sinks, and a high-end Wolf range. A dark navy lounge/media room next to the kitchen sports a wood-burning fireplace with a custom Italian marble surround and glass doors spilling out to an awning-topped balcony.

      Holding court by itself on the fifth floor is a posh primary suite flaunting a fireside sitting area, a large dressing room, and a luxe bath equipped with heated black limestone floors and a sky-lit walk-in shower. Two landscaped rooftop terraces have a sunroom lounge in the middle, while the basement holds a catering kitchen and a ton of storage space. Rounding it all out are surround sound, Lutron lighting, and water-filtration systems, plus an elevator that travels to each floor.

      Click here for more photos of the Manhattan residence.

      Evan Joseph/Evan Joseph Studios

      Authors

      Wendy Bowman

      Wendy Bowman is a real estate writer at Robb Report. Before that, she was a freelancer for Modern Luxury and several other media outlets, where she primarily covered luxury properties for…

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      Inside Senator Tim Sheehy’s $10.3 Million Montana Estate

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      Aerial firefighter and businessman Tim Sheehy was elected to his first term in the U.S. Senate this past November, and because he’s spending more and more time in the nation’s capital, he’s now offloading his sprawling Montana compound.

      Dubbed Bird Point, the seven-acre spread on Flathead Lake—the largest body of freshwater west of the Mississippi River—is located on a private peninsula and consists of a spacious main residence, a ranch-style guesthouse, and a more rustic guest cabin. Bryce Connery of Connery & Co. and Sean Averill of PureWest Real Estate hold the listing.

      The main bedroom in the guest cabin has an outdoorsy feel.

      Chris Neibauer

      “There are only so many seats in the front row—and Bird Point is one of them,” Connery said in a statement. “A private peninsula on iconic Flathead Lake represents a rare offering—especially at a time when Montana is experiencing unprecedented demand for premier properties.”

      The centerpiece of Bird Point is the traditional main house, which includes five bedrooms and four baths across almost 5,000 square feet. Here, a stone fireplace anchors the family room, and light woods warm up the kitchen. Almost every room offers a view of the lake, which you can also admire from several outdoor lounge spaces. The guest house provides an additional three extra bedrooms and two bathrooms, while the nearby log cabin is perfectly integrated with the wild Montana terrain, its vaulted ceilings and rough-hewn log walls echoing the untamed spirit of the landscape.

      The property includes 2,400 feet of shoreline, from which you can fish, swim, and boat.

      Jonathan Finch

      Among the grounds, fitness enthusiasts will be happy to find both pickleball and tennis courts. Fire pits dot the property, ideal for making s’mores on summer nights. And, along 2,400 linear feet of shoreline, there’s a new boat dock from which you can fish or head out for a swim. In the distance, the Mission Mountains frame your views, and Glacier National Park is a mere hour from the secluded estate.

      Montana has long been a haven for nature lovers with a penchant for wide open spaces. Last year, a massive 500-acre spread in Big Sky hit the market for a cool $31 million, and NFL legend Drew Brees brought his Montana vacation home to auction.

      Click here to see all the photos of the Montana estate.

      Jonathan Finch

      Authors

      Tori Latham

      Tori Latham is a digital staff writer at Robb Report. She was previously a copy editor at The Atlantic, and has written for publications including The Cut and The Hollywood Reporter. When not…

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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  

      Image Credit: Google Earth More