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    Inside Reese Witherspoon’s $36 Million Property Portfolio

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    Reese Witherspoon may have started as America’s sweetheart, but she’s since become a Hollywood powerhouse with serious business and real estate savvy. Over the past three decades, she’s built a career that spans acting, producing, and entrepreneurship, moving seamlessly between box-office hits, prestige television, and passion projects. That success has also translated into some of the industry’s top paychecks—at least $1 million per episode for television, including $1.2 million for The Morning Show, which she also produces.

    In 2012, the Legally Blonde star cofounded Pacific Standard, the company behind acclaimed films like Wild and Gone Girl. Four years later, she transformed it into Hello Sunshine, a women-driven media giant. In 2021, the company was sold for over $900 million to a Blackstone-backed media firm, with Witherspoon joining the board, staying involved in daily operations, and retaining significant equity. The company has delivered hits like Big Little Lies and Little Fires Everywhere and developed high-profile adaptations, including Where the Crawdads Sing and Netflix’s From Scratch.

    Her empire also extends to Reese’s Book Club, which counts 2.1 million followers and has seen 42 of its 50 picks land on The New York Times Best Sellers list—providing a built-in audience for future screen projects.

    Off-screen, the Academy Award winner has built a reputation as a real estate aficionado, buying, selling, and flipping homes across Los Angeles and her hometown of Nashville for the past two decades. Much like fellow celebrities such as Ellen DeGeneres, she’s developed a knack for turning high-end properties into investments. In recent years alone, she’s sold a Los Angeles property for $21.5 million—after paying under $16 million in 2020—and offloaded a Nashville home for nearly double what she paid in 2018.

    Many of these properties aren’t full-time residences but rather investments, retreats, or future projects. Still, each reflects Witherspoon’s sharp eye for style, comfort, and long-term value. From storybook Southern estates to sleek West Coast escapes and Bahamian hideaways, the homes of her collection are covered in more detail below.

    Nashville

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      Inside the $42 Million Bahamas Home Designed for Former J.Crew CEO Mickey Drexler

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      Mickey Drexler, the former CEO and chairman of J.Crew, not only has great taste in fashion but also has a keen eye for real estate. The retail legend commissioned the late French architect Thierry Despont to design several personal properties for him over the last few decades, including a rustic alpine retreat in Idaho and a sophisticated 9,000-square-foot townhouse in New York City, and in 2010, the architect completed a beachfront home in The Bahamas for Drexler and his wife Peggy. Known as Zehava and in the hands of only its second owner, the trophy estate is now being offered for a whopping $42 million, a sky-high figure that makes it the island’s most expensive single-family residential listing in The Bahamas.

      Nestled off the east coast of the island of Eleuthera, Zehava occupies three and a half acres within the prestigious Narrows enclave on Harbour Island, along what locals call Billionaire’s Beach, a pristine pink sand stretch of sand. Harbor Island has long been a somewhat under-the-radar hotspot for the world’s movers and shakers, including Taylor Swift, Tom Cruise, Diane von Fürstenberg and Barry Diller, David Letterman, and duty-free tycoon Robert Miller.

      Walls of windows give an intimate connection to the tropical surroundings.

      BOND Bahamas

      “Zehava represents a rare and unparalleled opportunity,” said broker Matthew Marco of Bond Bahamas. “With Thierry Despont’s visionary touch, this home blends timeless elegance with modern luxury, offering a living experience that is truly one-of-a-kind. Properties of this caliber, crafted by a master architect and located in such a coveted destination, seldom come to market—this is truly a once-in-a-lifetime chance to own a piece of architectural history in paradise.” 

      Sculpted from a combination of solid poured concrete, natural Brazilian hardwood, and cream-colored travertine stone, the 9,500-square-foot structure gains lightness thanks to a butterfly-style roofline that resembles lifted wings. Internally, the design makes the most of its waterfront vantage point with soaring high ceilings, dramatic expanses of glass, and foldable slatted wood walls that open to unite the indoor living spaces to the tropical landscape.  

      A two-bedroom cottage for guests adds to the sense of privacy and retreat.

      BOND Bahamas

      Despite its ample size, the main residence comprises just two bedrooms and two bathrooms, plus a powder room. In the commodious living room, a floor-to-ceiling wall of sliding glass doors lets the ocean air sweep right in while providing direct access to a covered patio. There’s also a more intimate den, a spacious dining room alongside a serving kitchen, with a galley-style chef’s kitchen clad in warm paneling off to one side. For visiting friends and family, there’s a two-bedroom, one-bath guest cottage.

      The grounds encompass broad decks that step down to palm-dotted lawns that roll down to the beach, sheltered terraces for escaping the sun, and a sunken pickleball court.

      Bedrooms spill onto water-view decks.

      BOND Bahamas

      Before the Zehava mansion hit the market, the highest-priced offering in the Bahamas was a $40 million property in Old Fort Bay dubbed Aspara. The oceanfront pad, which sold in April for $39.49 million, came with its own dock, a boat lift, and a private beach. 

      “The real estate market in the Bahamas has evolved to rival the world’s most exclusive destinations, such as the Hamptons, Malibu, and Palm Beach,” added Marco, who also represented the Aspara deal. “The demand for luxury properties here has surged as more discerning buyers seek not only a smart investment but also a serene, breathtaking environment to call home. The Bahamas is now firmly on the map as one of the world’s premier luxury markets.” 

      Click here to see more photos of Zehava. 

      BOND Bahamas

      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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      in Vacation Homes

      The Most Expensive Home in The Bahamas Just Sold for a Record $40 Million

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      Aspara, an ultra-opulent oceanfront mansion in The Bahamas, just traded hands for a record $39.49 million. Located within the exclusive Old Fort Bay community, the palatial estate marks the priciest residential sale publicly promoted on the island, according to Matthew Marco of BOND Bahamas, who represented both sides of the deal.  

      “Apsara is truly a one-of-a-kind gem, not only in The Bahamas but also in the entirety of the Caribbean,” said Marco in a press statement. “Having a stunningly designed and constructed estate with both oceanfront and canalfront access points, all while being located in the coveted and private Old Fort Bay enclave, Apsara is nothing short of the highest standard of luxury living.” 

      The oceanfront estate known as Aspara just set a real estate sales record in the Bahamas.

      Courtesy of BOND Bahamas

      The previous record was reportedly set in 2021 when country superstars Tim McGraw and Faith Hill offloaded their idyllic 20-acre private island, L’île d’Anges, aka Goat Cay, for a cool $35 million. 

      “Over the past few years, we’ve seen an uptick in high-profile, high-net-worth individuals looking for truly one-of-a-kind trophy residences across The Bahamas,” added Marco. “The sheer geographic constraints of the island only allow for so many waterfront residences like Apsara, making these exclusive Bahamian properties so coveted that their sale prices are now matching those of the largest U.S. markets.” 

      The original listing for Aspara touted its 150 feet of turquoise waterfront along with 150 feet of canal frontage, plus a private dock and boat lifts. The abode itself measures a whopping 14,000 square feet and features eight bedrooms and 10 full bathrooms.  

      A spacious loggia overlooks the swimming pool and ocean.

      Courtesy of BOND Bahamas

      The posh pad has a contemporary flair to it with a slew of amenities, including a state-of-the-art fitness center, a steam room, an elevator, and an 876-bottle glass-enclosed wine cellar. There’s also a custom gourmet chef’s kitchen for indoor entertaining, as well as a sunken dining area for alfresco meals. The home wraps around a lush interior courtyard and is lined with walls of glass that open up to sunny terraces, sprawling loggias, and a massive infinity pool. From here, you can walk down to your own private sandy beach. 

      “The Bahamas truly has everything a high-net-worth individual would look for in a luxury beachside residence,” added Marco. “The warmth of the people, the sophisticated infrastructure, the banking capabilities, the tax incentives, the gracious privacy, the stable government, and, of course, the most beautiful natural landscape in the world, all make the Bahamas a smart investment.” 

      Click here to see more photos of Aspara.

      Courtesy of BOND Bahamas

      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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      in Vacation Homes

      Aspara Bahamas in Photos

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      Published on April 30, 2024

      Courtesy of BOND Bahamas

      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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      in Vacation Homes

      This 430-Acre Private Island in The Bahamas Can Be Yours for $45 Million

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      Royal Island, a swanky Caribbean oasis in The Bahamas, awaits its next king or queen and their lucky retinue of family and friends.

      Less than a 20-minute boat ride from the picturesque North Eleuthera, famous for its pink sand beaches, the 430-acre private island is asking for a whopping $45 million, The Daily Mail reported. However, you can’t really put a price on paradise, can you?

      Altogether, the palatial spread has five residences, a private gym, a yoga center, a spa, and a large oval-shaped swimming pool. The turnkey property also comes with its furnishings, so essentially all you have to do is wire the purchase funds and pack your toothbrush.

      In 2021, Royal Island appeared in season one of the travel-centric Netflix series The World’s Most Amazing Vacation Rentals, hosted by Megan Batoon, Jo Franco, and Million Dollar Listing New York star Luis D. Ortiz. Awarded as one of the top resorts on the planet by Condé Nast Traveler, the idyllic private island was bookable earlier this year for a hefty $18,500 per night, Forbes reported.

      At the heart of the Caribbean compound is an oval-shaped swimming pool.

      J. Christie & Vladi Private Islands

      Surrounded by nothing but crystal-clear turquoise waters, the secluded island makes for the perfect party pad and can host up to 18 people at once.

      Royal Island will accommodate 18 guests among its five one-bedroom beachfront villas and separate guest house. Each of the tropical-inspired bungalows is nestled among the lush greenery and sports vaulted ceilings, an en suite bathroom, and a spacious wraparound deck for languidly gazing out toward the ocean.

      Accommodations on the 430-acre island include five waterfront villas.

      J. Christie & Vladi Private Islands

      “Royal Island, as set up currently, is excellent for private gatherings,” notes the listing, which is held by Vladi Private Islands. A perfect party pad for hosting friends and family, the secluded island has its own bar and restaurant within the grounds. 

      There are plenty of ways to keep busy during the day, but, naturally, the highlights of the property are the water sports. Think everything from snorkeling to paddleboarding, jet skiing, and kayaking.

      Of course, if you’re looking to create an even more epic escape, the island getaway was granted preemptive approval in 2007 for additional development, including an expansive marina. There are also plans for an 18-hole waterfront golf course; however, the sky is really the limit here. And if you’re ever worried about feeling too isolated, rest assured you’re approximately 40 miles northeast of Nassau, the capital of The Bahamas.

      Click here to see all the photos of Royal Island. 

      J. Christie & Vladi Private Islands

      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, dining, travel and topics…

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      in Vacation Homes

      Royal Island in Photos

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      Published on January 11, 2024

      J. Christie & Vladi Private Islands

      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, dining, travel and topics…

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      in Vacation Homes

      A First Look at The Ocean Club, Four Seasons Residences in The Bahamas

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      You can now permanently live in one of the world’s most glamorous resort communities. 

      A quick jaunt from Miami, the famed Ocean Club, now a Four Seasons Resort on Paradise Island in the Bahamas, has long been an escape for the world’s elite. The Ocean Club first opened in 1962 and, thanks to its wealthy and well-connected bon vivant businessman owner Huntington Hartford II, immediately became the ultimate Caribbean getaway for a glamorous assortment of international jet-setters and multi-millionaires, Hollywood A-listers, and European royalty. Slim Aarons was a regular; The Beatles recorded a video here; and Zsa Zsa Gabor was a frequent patron. In 2017, Four Seasons was brought in to brand and manage the property, as well as expand the resort’s offerings while honoring its venerable legacy.

      Floor-to-ceiling windows open to covered terraces.

      Ocean Club, Four Seasons Residences, Bahamas

      “The Ocean Club has that beautiful, elegant, understated sense of tranquility that very few places get, especially in Nassau or Paradise Island,” says Reid Boren, managing partner at Two Roads Development, a partner on the project. “There’s a really loyal following for The Ocean Club, and families have been coming here for generations.” 

      The brand recently unveiled the soon-to-come Ocean Club, Four Seasons Residences, Bahamas, in partnership with Two Roads Development and Access Real Estate to bring a new ownership opportunity to the Bahamas. Set to open in 2027, the 67 turnkey residences will sit in close proximity to the hotel and will be managed by Four Seasons. The residences, designed by SB Architects and Champalimaud Design, will contain between two and five bedrooms and span from a roomy 3,124 to a commodious 7,459 square feet. There will also be a select number of penthouses measuring almost 5,300 square feet, each with a private pool.

      Pricing ranges from $6.5 million to $23 million, and, when not in use, owners can opt to put their Bahamian getaways into a vacation rental pool. 

      “The residential aspect is an experience that regular guests of The Ocean Club want,” he says. “When you’re there, you have your own home and space with your family and friends, yet you can still feel like you’re at the resort.”

      A spacious ocean view terrace is the perfect spot for alfresco meals.

      Ocean Club, Four Seasons Residences, Bahamas

      Each home will have a neutral color palette infused with warm, organic materials and will feature a sophisticated take on classic, relaxed Bahamian style, with subtle hints of pink blush in the stonework, stately columns, and deep terraces. There will be seamless access to the outdoors from nearly every room.

      The residences are split between four low-rise structures with beachfront villas along the first levels of each building. At the center of the residential complex is an expansive resident-only pool area and pool deck with a private clubhouse and private cabanas. There’s also direct beach access. 

      The residences will be separate from the resort and have a dedicated team exclusively to service the residents. There will also be a bevy of exclusive amenities in addition to the pool, including an owners’ library, a wine cellar and rum room, a co-working space, a children’s playroom, a media room, indoor and outdoor spa treatment rooms, a fitness center, a beachfront restaurant and bar, and private dining rooms.

      The many amenities include a resident-only library.

      Ocean Club, Four Seasons Residences, Bahamas

      Should you want to visit the resort, residents have access to the legendary Ocean Club’s five-star amenities. In addition to three swimming pools and Versailles-inspired gardens that showcase a 12th-century Augustinian cloister, there’s the restaurant Dune, helmed by celebrity chef Jean-Georges Vongerichten, six Har-Tru tennis courts, and eight Balinese-style spa villas. The resort also offers daily yoga and Pilates, as well as a shuttle service to an 18-hole Tom Weiskopf-designed championship golf course.

      The Ocean Club isn’t your typical Four Seasons Resort; it’s infused with period details, European-style gardens, and glamorous grounds. There’s a 12th-century Augustinian cloister and impeccable gardens modeled after Versailles. It’s also set along a five-mile stretch of pristine, white-sand beach.

      Click here for more photos of The Ocean Club, Four Seasons Residences, Bahamas.

      Ocean Club, Four Seasons Residences, Bahamas More

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      in Vacation Homes

      From Mexico to Sardinia: Here Are the Most Expensive Airbnb Beachfront Rentals Around the World

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      Nothing says vacation like a trip to the beach. But how much would you splash out for a totally over-the-top rental? 

      For those yearning for a luxury weekend by the sea, a new study combed through the most expensive beachfront Airbnb listings in every country and came up with a ranking of the world’s top 10 priciest vacation properties. To put things into perspective, the report found that the average Airbnb rental goes for $137 per night. Naturally, the nightly rate for a billionaire-style villa on the beach is going to cost way more. Let’s get into it.  

      The most expensive beachfront Airbnb is an $18,000-per-night private island in the Bahamas.

      Courtesy of Airbnb

      There are two properties that rank as the most expensive Airbnbs on the planet. For an eye-watering $18,000 a night, you can book a stay at Middle Cay, an idyllic private island in the Bahamas, or live it up at Casa del Oso, a 10-bedroom waterfront mansion in Punta Mita, Mexico.

      In the third spot is Villa Harrah in Glenbrook, Nevada, which ranks as the most expensive rental in the United States. The 20,000-square-foot Lake Tahoe chalet, originally built in 1963 by casino operator William F. Harrah, runs a cool $17,000 per night. In comparison, the next most expensive vacation rental in the U.S. is the $11,000 per night Villa Salt Acres in Stonington, Connecticut, which includes 2,000 feet of pristine coastline with 400 feet of private beach, along with a boat dock, a tennis court, a movie theater, and a wine cellar.  

      Villa Harrah on Lake Tahoe is the priciest beachfront vacation rental in the United States.

      Courtesy of Airbnb

      Coming in at the fourth spot is Mansion Villa at Daios, a sea-facing retreat in Crete. The $16,995-per-night residence on Daios Cove, the most expensive Airbnb in Europe, offers panoramic ocean views, an infinity pool, a sprawling stone terrace, and an indoor spa area that’s replete with a sauna, a massage room, and a gym.

      If you’ve got $16,311 to burn, you can enjoy a stay at Finca J in the medieval Spanish village of Begur, and for $15,000, you can book a stay for up to 24 guests at Villa Punta Aguila inside the swanky Casa de Campo Resort in the Dominican Republic.  

      CieloMar in Costa Rica ranks seventh on the list and goes for $13,265 per night; the villa can accommodate up to 12 guests in six bedrooms. The home is shaped like the bow of a ship and comprises every enviable amenity imaginable, from a volcanic stone-lined infinity pool to a wet bar and a Zen garden.  

      Rounding out the top 10 are Crystal Springs, a $12,500-per-night beachfront compound in Barbados that provides a staggering 12,000 square feet across six buildings serviced by a staff of 14; the $12,000-per-night Pearns Bay House in Antigua, which can accommodate up to a dozen guests; and, for $11,946 per night, there’s Villa Hortensia on the coast of Sardinia. More

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      International Treasure? Nicolas Cage Is Unloading His Private Bahamas Island for $7.5 Million

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      Nicholas Cage is feeling the unbearable weight of one massive private island.

      The Oscar-winning actor, who once owned as many as 15 luxury homes, sold off the majority of his real estate portfolio roughly a decade ago to pay back a hefty tax debt. (You might also remember reading how he blew his $150 million fortune on outlandish things like a… dinosaur skull.) But he’s still struggling to offload Leaf Cay in the Bahamas.

      The idyllic island, which is located in the Exumas archipelago about 85 miles southeast of Nassau, was reportedly purchased by the Hollywood heavyweight in 2006 for $3 million. Spanning a total of 30 acres, it offers three immaculate beaches, as well as protected deep water access for anchoring yachts or tenders.

      Leaf Cay comes complete with three beaches. 

      AP/Christie’s International Real Estate

      What’s more, the island is completely undeveloped and essentially a blank canvas for buyers. According to the listing, which is held by Christie’s International Real Estate, there are “full development approvals” to construct five cottages, along with additional support buildings. You also have the green light to convert one of the island’s two large ponds into a marina.
      Leaf Cay is in a great location, too. It’s surrounded by some 365 cays and islands that stretch more than 120 miles and feature some standout attractions. The nearby Bock Cay, for example, is reportedly welcoming a $75 million development that will include a golf course, luxury resort, marina and helipad. Leaf Cay is also surrounded by natural wonders and there is excellent fishing in the nearby Exuma Sound.

      One of the island’s two large ponds can be converted into a marina. 

      AP/Christie’s International Real Estate

      “Leaf Cay represents the last great private island opportunity at a reasonable price for a fee simple island with crystal clear title, like the beautiful waters that surround it,” Christie’s writes on the listing.
      Though Christie’s says Leaf Cay’s price is available upon request, another site called Private Islands Inc. has the island listed at $7.5 million. That means The Unbearable Weight of Massive Talent star will have made a profit of $4.5 million over 16 years. Maybe he can buy himself another dinosaur skull. More