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    Jeff Bezos Just Dropped $90 Million on a Third Indian Creek Island Property

    Jeff Bezos’s South Florida spending spree continues.

    The Amazon founder has splashed out a whopping $90 million in an off-market deal for a third waterfront estate on the coveted Indian Creek Island, Bloomberg reported on Tuesday. According to the outlet, Bezos, who recently landed in third place on Forbes’s ranking of the world’s richest people, will live at the six-bedroom mansion while work is done on the two other properties he previously purchased.

    Tax records reveal that the Blue Origin founder’s new digs were last sold in 1998 for just $2.5 million, which goes to show how much home prices on the guard-gated Billionaire Bunker have skyrocketed. The Real Deal reported that the roughly two-acre spread was originally built in 1956 and later expanded upon in 1986 and once again in 2014. Altogether, the palatial pad features a swimming pool, a boat dock on Biscayne Bay, and 10,000 square feet of living space. 

    An aerial view of Jeff Bezos’s new home on Indian Creek Island, his third purchase on the guard-gated enclave.

    Google Earth

    Last November, the former CEO of Amazon announced in the most modern of ways—on his Instagram—that he was officially relocating from Seattle to Miami, noting that he wanted to be closer to his parents and his fiancée, Lauren Sanchez. “I’ve lived in Seattle longer than I’ve lived anywhere else and have so many amazing memories here,” he captioned the post. “As exciting as the move is, it’s an emotional decision for me. Seattle, you will always have a piece of my heart.”

    Several months earlier, in August 2023, Bezos dropped $68 million in a clandestine, off-market transaction for a three-bedroom, three-bath home on the man-made barrier island. At the time, he was reportedly eyeing the house next door too, and it was only a few months before he worked out another under-the-radar deal to acquire it for $79 million. The existing home, with seven bedrooms, spans more than 19,000 square feet.

    The estate includes a swimming pool, a pool house, a putting green, and a small dock.

    Google Earth

    Bezos now owns three of the roughly 40 homes on the 300-acre island, at a cost of nearly a quarter billion dollars—$237 million, to be exact.

    Other notable figures that reside on Indian Creek include Tom Brady, Jared Kushner and Ivanka Trump, and investor Carl Icahn. The community, which is connected to the mainland via a short bridge, sports a private 18-hole golf course, and residents have access to the country club. 

    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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    A Healthcare Mogul Is Selling Three Oceanfront South Florida Properties for $76 Million

    A trio of oceanfront properties owned by Michigan-based health-care entrepreneur Mark Mitchell are simultaneously up for sale in South Florida. Consisting of two mansions and a vacant parcel resting in the exclusive Veromar neighborhood of Vero Beach, directly overlooking the Atlantic, the total asking price is a whopping $76 million. The two homes are listed separately by Cindy O’Dare, Richard Boga and Kristin Dobson with the O’Dare Boga Dobson Group of ONE Sotheby’s International Realty for $42 million and just under $20 million, while the spare lot is asking $14 million.

    The properties were acquired by Mitchell and his wife Colby in two separate deals. The couple purchased a contemporary residence at 3700 Ocean Drive from Alloy founder and chairman Katherine McConvey in summer 2021 for $16.8 million, and subsequently picked up two adjacent lots at 3750 Ocean Drive and 3746 Ocean Drive also owned by the developer for $4.2 million. Together, the three-parcel spread spans over 2.7-acres of land and 400 feet of waterfront footage.

    3700 Ocean Drive features a main house and guesthouse, for a total of eight bedrooms and 12 bathrooms in 18,000 square feet of living space.

    Pat Vidas

    Containing 18,000 square feet of living space with eight bedrooms and 12 baths, the largest modernist structure (above) was built and designed in 2014 by architect Erik Helgen in collaboration with Alloy, then renovated inside and out to the tune of $2 million by the Mitchells. Sitting on roughly 200 feet of oceanfront footage, the walled and gated abode is highlighted by a soaring glass-lined living area centered around a massive two-way fireplace and a pair of fiber-optic lighting installations by Sharon Marston.

    Elsewhere is a sumptuous master retreat boasting a marble and teak bath spotlighted by a steam shower and shell-shaped tub nestled alongside a linear fireplace. Other amenities include four fireplaces, several kitchens, dual offices, a gym, wet bar-equipped screening room and Savant home-automation system, with the palm-laced grounds spanning 1.4 acres and hosting a fire-pit, an 80-foot infinity-edge pool flanked by a tiki hut, and an al fresco lounging and entertaining patio with a pizza oven. There’s also a separate two-story guesthouse and garage space for up to 10 vehicles.

    3750 Ocean Drive has seven bedrooms and nine bathrooms in just over 7,600 square feet.

    M. James Northen

    As for the smaller of the two dwellings (above), it’s perched on a 0.6-acre parcel offering 100 feet of waterfront footage. Completed this year by architect Gregory Anderson and Waters Edge Estates—and originally offered for $21 million, before having been recently reduced to just under $20 million—the custom-built structure features seven bedrooms and nine baths spread across a little more than 7,600 square feet of two-level living space offering a mix of limestone and wide-plank hardwood floors, wood-beam ceilings and picturesque ocean views via floor-to-ceiling walls of glass.

    A great room outfitted with living, dining and family room areas connects to a gourmet kitchen decked out with custom cabinetry, marble countertops, an eat-in island, a butler’s pantry, and top-tier Miele, Sub-Zero and Wolf appliances; and other standout features include an elevator, two primary bedrooms, an office space and entertainment room with a wet bar. A beachfront lanai sporting a saltwater pool and spa also can be found on the premises, complemented by a guesthouse resting atop the three-car garage.

    3746 Ocean Drive is primed for an 11,000-squre-foot estate.

    M. James Northen

    Rounding it all out is the 0.69-acre vacant parcel (above), which features 100 feet of direct ocean frontage and includes plans available for an 11,000-square-foot estate, per the listing.

    Mitchell founded the nationwide house-call service Visiting Physicians Association and U.S. Medical Management, which sold to Centene Corp. in 2019 for around $325 million. Currently managing partner of Mitchell Family Office, a private-equity firm that invests in health-care ventures, he also maintains a primary home in Michigan, as well as Daxton Hotel in the Detroit suburb of Birmingham.

    Click here for more photos of Mark Mitchell’s Florida compound.

    Pat Vidas More

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    A Private Island Off the Florida Keys Returns to Market for $75 Million

    Tired of renting vacation homes with obnoxious and nosy neighbors? Prefer your tropical getaways to be hideaways that are far from the maddening crowd? Why settle for a rental at all when you could have your own private island sanctuary instead? 

    Pumpkin Key, a lush 26-acre isle off the Florida Keys, is looking for its next owner—and at a reduced rate. The picturesque spread has reemerged on the market for $75 million, a $20 million price chop from back in 2020 when it was listed for $95 million. Located in Key Largo’s serene Card Sound Bay, the tropical compound includes automatic membership to the Ocean Reef Club, an exclusive private club community that’s less than five minutes by boat. The island is also a quick 10 minutes from South Beach via helicopter. 

    Pumpkin Key, a 26-acre private island off the coast of Florida, includes a pristine private beach.

    Become Legendary

    Whether as a private retreat, legacy investment, or a sanctuary for generations, this property stands as a beacon of distinction and exclusivity,” notes the listing, which is held by Compass agent Liz Hogan. According to Mansion Global, Pumpkin Key was originally purchased in 1970 by a family of industrialists hailing from Chicago. At the time, the island was undeveloped and uninhabitable. Today, nearly 75 years later, the island is a serene retreat that is totally self-sufficient when it comes to water and electricity. 

    So, what does $75 million get you? Aside from the massive amounts of privacy and tropical tranquility, the buyer of Pumpkin Key will get a three-bedroom residence, a pool house, three guest apartments, and a pristine stretch of beach. There are two side-by-side tennis courts (one also has pickleball court lines) that double as a helipad. There’s also a large swimming pool and a 20-slip marina that offers plenty of room to park your megayacht along with a whole bunch of your friends’ boats. Paved golf cart paths link the island’s various locales.

    For those who prefer their vacation retreat to not be so isolated, the island has 12 one-acre vacant lots for development. The homesites could be sold off to friends (or strangers) or built out and added to the existing structures to create a super-sized island compound. 

    The property also has two side-by-side tennis courts that can serve as a helipad.

    Become Legendary

    The buyer of Pumpkin Key will also take possession of a waterfront home on Key Largo, within the 2,500-acre, guard-gated Ocean Reef Club. The resort community, which is accessible by car, comprises 1,700 mostly waterfront homes, and residents have access to all of the club’s many swanky luxuries. Think pristine championship golf courses, a 175-slip world-class marina, a slew of fine dining restaurants, and a state-of-the-art spa and fitness center. Ocean Reef even sports its own private airstrip if you plan on flying in on your PJ.

    Click here to see all the photos of Pumpkin Key. 

    Become Legendary

    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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    A Hot Dog Mogul Is Serving Up This Oceanfront Florida Penthouse for $32.5 Million

    Totally bummed you can’t swoop in and grab America’s most expensive home that just hit the market in Southwest Florida with an eye-popping $295 million price tag? Now’s your chance to snap up the next best Naples thing, and it’s currently up for sale. But you’ll still need almost $33 million to pick up the keys to the freshly remodeled penthouse, which would set a record for the priciest resale unit in the affluent area if the place goes for anywhere near that amount.

    Property deeds show the residence was last sold in fall 2022 for $11 million. Dick Portillo—the Chicago-born founder of the Portillo’s restaurant chain, best known for its Chicago-style hot dogs and Italian beef sandwiches—subsequently embarked upon an extensive renovation of the 2002-built premises in collaboration with an investment team consisting of C&E Builders and Theory Design’s Ruta Menaghlazi. The listing is held by The Earls | Lappin Team of John R. Wood Christie’s International Real Estate.

    The spacious living room is flanked by a fireside lounge area.

    Naples Kenny Photography

    Resting on the 20th floor of The Seasons at Naples Cay—a gated beachfront high-rise building bordering Park Shore to the south and Pelican Bay to the north—the revamped abode offers five bedrooms and seven baths in almost 12,000 square feet of living space boasting herringbone oak floors, high ceilings and designer lighting throughout. Floor-to-ceiling walls of glass and 4,800-plus square feet of outdoor terraces also offer up panoramic vistas stretching from the Gulf of Mexico and Outer Clam Bay to the city lights of Naples.

    Highlights include an elevator-accessible foyer leading to an open-plan great room holding a fireside living room and dining area, along with a gourmet kitchen sporting champagne eucalyptus cabinetry, white Macaubas quartzite countertops, an expansive eat-in island, top-tier Miele appliances and an accompanying breakfast nook flanked by a family room. A secluded master wing features a water vapor fireplace, wraparound balcony with a spa, separate morning lounge, sauna-equipped fitness studio, and dual dressing rooms and baths.

    The ocean-view terraces come complete with an outdoor kitchen and spa surrounded by a “living” wall.

    Naples Kenny Photography

    Elsewhere are four additional en-suite bedrooms, including one with its own kitchen and living area, along with glitzy amenities ranging from a backlit onyx entertainment bar and glass-encased wine vault to a handsome study warmed by a fireplace; and topping it all off are plenty of community amenities—courtesy of a hefty $11,563 monthly HOA charge—which include a guard-gated entry, 24-hour doorman, swimming pool, fitness center and billiards room.

    A self-made billionaire and longtime real estate investor, Portillo also maintains an additional Naples condo and has renovated several properties in the Chicago area.

    Click here for more photos of Dick Portillo’s Florida penthouse.

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    The ‘Queen of Versailles’ Is Looking to Flip a Palatial NYC Condo for $19.5 Million

    Jackie and David Siegel, stars of the cult-favorite 2012 documentary The Queen of Versailles, are at it again. This time, the opulence-loving real estate power couple has returned to market a swanky New York City penthouse they bought together just last year.

    Now asking $19.5 million, the Siegels originally shelled out $8.7 million for the Tribeca duplex, as The New York Post first reported. The palatial pad spans 4,800 square feet and comprises three bedrooms, three bathrooms, two powder rooms, and a sprawling private terrace. The apartment is atop 49 Chambers Street, an iconic Beaux Arts building that was built in 1912 by architect Raymond F. Almirall and once served as the former home of the Emigrant Industrial Savings Bank. 

    Jackie and David Siegel are aiming to flip their duplex penthouse in Manhattan for $19.5 million.

    Evan Joseph Photography for Douglas Elliman

    “49 Chambers is one of Downtown’s most recognizable landmarks,” Douglas Elliman agent Kirsten Jordan, who’s representing the property along with colleague Lindsay Coleman, tells Robb Report via email. “The facade is so intricate, and then inside you have this iconic contemporary penthouse with sleek interiors and massive living spaces.”

    The home itself has an open floor plan, and Jackie told The Post that they often use the apartment for entertaining. The couple even hosted the cast of the Queen of Versailles Broadway musical starring Kristin Chenoweth at the palatial pad and threw a party for the Victoria’s Voice Foundation, which they founded in 2015.

    The kitchen is equipped with SubZero, Gaggenau, Wolf, and Miele appliances.

    Evan Joseph Photography for Douglas Elliman

    The chef’s kitchen is sleek, clean-lined affair that’s decked out with custom Cypress wood cabinets with the waterfall island, countertops, and backsplash all clad in marble. Elsewhere, the living room opens to an 850-square-foot landscaped terrace with a grill, sink, refrigerator, outdoor speakers, and tons of lush greenery.

    Back inside, the primary suite is equipped with custom walk-in closets and an ensuite bathroom that steals the show with double vanities, crowned mirrors, a freestanding soaking tub, and heated floors. “It’s a great apartment with endless square footage, amazing views on three sides, and a private terrace. A palace of a pied-a-terre,” adds Jordan.

    Currently, the Sigels are in the midst of finishing their main residence, a 90,000-square-foot behemoth in Orlando, Florida, that has been two decades in the making. Once completed, the Versailles-aspiring mega-mansion will include a 35-car garage, a 150-person dining room, a British-style pub, and a replica of the cabin of a private jet. After several setbacks, including being flooded during Hurricane Ian in 2022, Jackie told the newspaper she’s hoping construction on the mega-manse will finally be finished “around a year from now.” The process was recently featured in the HBOMax series Queen of Versailles Reigns Again.

    Click here to see all the photos of Jackie Siegel’s NYC penthouse. 

    Evan Joseph Photography for Douglas Elliman

    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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    Tennis Champ Caroline Wozniacki’s Miami Penthouse Swings Onto the Market for $42.5 Million

    Game, set, match. Tennis pro Caroline Wozniacki and her husband, former New York Knicks player David Lee, have served their sprawling Florida penthouse on the market for a whopping $42.5 million with Dina Goldentayer of Douglas Elliman. Located on Fisher Island, an exclusive 216-acre enclave off the coast of Miami, the waterfront condo is perched at the top of the 10-story Palazzo Del Sol development.

    The couple, who married in 2019, originally purchased the palatial pad back in 2021 for $18.7 million, property records show, and according to The Wall Street Journal, they upgraded to the penthouse apartment after selling a different unit in the luxury Kobi Karp-designed complex that same year for a cool $16.25 million.  

    The penthouse features a custom bar that overlooks Biscayne Bay and the South Beach skyline.

    Dina Goldentayer/Legendary Productions

    Altogether, the 7,000-square-foot spread comprises five bedrooms and five full baths across its two floors. There’s an additional 5,000 square feet of outdoor space divided between two terraces. Goldentayer told the WSJ that after Wozniacki and Lee bought the residence, they went on to transform the raw space by reworking the floorplan and adding high-end touches such as white oak herringbone flooring throughout and a striking custom bar. 

    The lavish duplex opens to a dramatic great room with soaring 18-foot ceilings and glass pocket doors. The huge space is broken up into four different entertainment spaces, including a hosting salon, a bar area, a TV watching space, and a formal dining area. Elsewhere, the kitchen feels super sleek and contemporary. Here, you’ll find top-of-the-line Gaggenau appliances, a swanky dine-in marble island, a massive wine wall, and an Art Deco-inspired hood above the stove.

    The residence sports a private rooftop lap pool alongside an alfresco dining area.

    Dina Goldentayer/Legendary Productions

    Of course, the aerie has a few aces up its sleeve. For starters, the screening room is equipped with a state-of-the-art Bang & Olufsen sound system, and on one of the terraces, there’s a hot tub and fire pit. The real pièce de résistance, however, is without a doubt the private rooftop pool, which has sweeping views of Biscayne Bay.

    The 47-unit condominium, which was completed in 2016, is positioned on the north end of Fisher Island and is complete with its own fitness center, movie theater, hair salon, and spa treatment rooms. The ultra-elite, members-only island is known for being one of the priciest ZIP codes in the country and has counted Oprah Winfrey, Mel Brooks, Julia Roberts, and Andre Agassi among its residents.

    Click here to see all the photos of Caroline Wozniacki’s Miami penthouse. 

    Dina Goldentayer/Legendary Productions

    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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    MLB Legend Johnny Damon Lists His Massive Florida Mansion for $30 Million

    Move over, Walt Disney World. Retired MLB star Johnny Damon built his own adult playground in Florida, and the over-the-top Florida mansion is now on the market for an eye-watering $30 million.

    Located in Windermere, a suburb of Orlando, the sprawling property sits on a nearly five-acre lot with 540 feet of frontage along Lake Butler. According to The Wall Street Journal, which first reported on the listing, the retired MLB star and his wife, Michelle, acquired the land in 2007 for $4 million. The 30,000-square-foot estate was later completed in 2010, and from the looks of it, no expense was spared in the construction.

    “The owners really took the time to envision, design, and build a dream home, one that meets every standard of luxury, ideal for both family living and also perfect for entertaining,” said Alice Anne Jackson with Corcoran Premier Realty in a press statement.

    Johnny Damon’s mansion in near Orlando includes a two-lane bowling alley with graffitied walls.

    Uneek Image

    Altogether, the palatial residence comprises nine bedrooms and a whopping 15 bathrooms. In terms of amenities, well, it’s got just about every perk you could think of. Hair salon? Check. Two-lane bowling alley. Of course. A gym? As a matter of fact, there are two! The abode also features a cigar lounge, an arcade, a sports bar, a movie theater, a music room, plus a sauna, steam room, and meditation area. “You never run out of things to do,” Damon told the WSJ.

    The 30,000-square-foot home includes a custom sports bar.

    Uneek Image

    The primary suite is ensconced in a dedicated wing on the first level and is decked out with a coffee bar, a two-story closet, and both indoor and outdoor showers. Elsewhere, the kitchen is any aspiring chef’s dream, equipped with large islands, a walk-in pantry, and a breakfast bar. There’s also a separate catering kitchen, because why not? 

    Outside, the grounds could definitely be mistaken for a theme park. There’s a massive, resort-style saltwater pool with a grotto, spa, slide, and even a swim-up hibachi grill and bar. For the adventurous types, you can soar through the skies on the property’s zipline or channel your inner athlete on the sports court.

    The backyard has a saltwater swimming pool with a waterfalls and a grotto.

    Uneek Image

    The former outfielder for the New York Yankees and Boston Red Sox told the newspaper he’s selling the home so he and his wife Michelle can travel more now that their six kids are grown. (Damon has two other kids from a previous marriage.) Since Damon’s retirement in 2012, the two-time World Series champ and his wife have made their rounds the reality TV circuit. Most recently, they appeared (twice!) as charter guests on Bravo’s Below Deck. Damon also had a brief stint on Dancing With the Stars in 2018 and Celebrity Apprentice, hosted by Donald Trump. In 2020, he was even appointed to Donald Trump’s Council on Sport, Fitness, and Nutrition. 

    Click here to see all the photos of Johnny Damon’s Florida mansion.  

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