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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.

    Naples Kenny Photography More

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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


    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


    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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    A Tech CEO’s Oceanfront Florida Mansion Is Up for Grabs at Nearly $22 Million

    After barely two years of ownership, Mike Tuchen has decided to hoist his Florida estate on an exclusive Hillsboro Beach barrier island in northeast Broward County back on the market. The San Francisco-based tech executive is asking a smidge under $22 million for the waterfront spread, which rests on almost three-quarters of an acre of land tucked between the Atlantic Ocean and Intracoastal Waterway.

    The CEO of Onfido, a global provider of identity and verification services, and his wife Sarasina purchased the property from Russian casino owner Maxim Smolentsev for almost $17 million in spring 2021. Built and designed in 2009 by Everton Development, the stately pink and white-trimmed structure offers five bedrooms and 10 baths spread across nearly 11,000 square feet of chic living space adorned throughout with a mix of marble and dark hardwood floors, decoratively trimmed walls and high wood-beam ceilings.

    The home is located on a barrier island known as “Millionaire’s Mile,” between the Intracoastal Waterway and Atlantic Ocean.

    The Carroll Group

    “This trophy estate represents the pinnacle of coastal living, offering the best of both worlds overlooking a pristine beach on one side and the Intracoastal with a boat dock on the other,” says listing agent Chad Carroll of The Carroll Group at Compass. “The property offers everything one could ever need; from prime location and gated privacy to immaculate design and incredible amenities, the level of luxury is incomparable.”

    Sited in the sought-after “Millionaire’s Mile” community, about 20 minutes north of Fort Lauderdale, the three-story structure boasts numerous amenities, including a club room, golf simulator, bar, wine cellar and gym. There’s also a spacious five-car garage, plus 100 feet of waterfront footage on the Intracoastal sporting a 70-foot dock and 30,000-pound boat lift.

    A cozy fireside club room is the ideal spot for entertaining guests.

    The Carroll Group

    Especially standing out inside is an entry foyer flanked by recessed wall niches. From there, a living room with a fireplace is highlighted by sliding glass doors spilling outside, a formal dining room has a built-in buffet, and a gourmet kitchen is outfitted with an eat-in island and top-tier stainless appliances. An adjacent dining area connects to a family room, while a posh upstairs master retreat is tricked out with a sitting room, private balconies, and a luxe bath flaunting a soaking tub and separate rainfall shower.

    Outdoors, the palm-laced grounds are showcased by Italian marble terraces a summer kitchen, and pool and spa abutting a grassy lawn and lounging patio, along with steps leading directly to the beach below.

    A set of steps leads directly to the beach below.

    The Carroll Group

    Per property records, the Tuchens also maintain an ocean-view residence in Pebble Beach, Calif., that they paid $6 million for a little more than six years ago, back in winter 2017.

    Click here for more photos of Mike Tuchen’s Florida house.

    The Carroll Group More

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    A Mortgage Mogul’s Waterfront Estate in South Florida Just Sold for a Record $30 Million

    Just 40 days after it hit the South Florida real estate market with a hefty $33 million ask, a lavish waterfront home in Fort Lauderdale’s gated Harbor Beach enclave already has sold for the still substantial amount of $30 million, as first reported by The Wall Street Journal.

    Broward County’s priciest real estate transaction so far this year, the deal also set a square footage price record for the area at $3,174 per square foot.

    But it’s not quite the most ever paid for a home in the region nestled between Miami-Dade and Palm Beach counties. That milestone occurred this past August, when a billionaire self-storage tycoon doled out $32.5 million for a 13,060-square-foot waterfront spec mansion in the Lauderdale Harbours community.

    Though the buyer is currently unknown, records show the seller of the Harbor Beach spread is Ronald Leonhardt Jr., the founder, president and CEO of Ohio-based CrossCountry Mortgage, who paid hotelier Mikhail Avrutin $23 million for the property a little more than two years ago.

    The double-height living area is spotlighted by a massive marble fireplace, walls of glass and an adjacent 200-bottle wine display.

    Daniel Petroni

    Completed on spec in 2021 by Randall Stofft Architects and Sarkela Corp., the mansion rests on a third of an acre, amid 120 feet of water frontage on the eastern side of the Intracoastal Waterway, and offers six bedrooms and nine baths sprawled across almost 9,500 square feet of two-level living space decked out with Duchateau oak floors, Terzani light fixtures, and walls of glass overlooking picturesque water and skyline views.

    Posh amenities range from a glassy wine display that holds 200 bottles and wet bar-equipped game room/lounge, to a roof deck and dock big enough to accommodate a mega-yacht.

    Additional highlights include a living room sporting a soaring marble fireplace, along with a “show” kitchen equipped with Italian cabinetry, an eat-in island, top-tier appliances, a breakfast nook and an additional prep kitchen. There’s also a sumptuous upstairs master retreat boasting a fireside sitting area and balcony, as well as dual closets and baths.

    The master retreat comes complete with two baths, including this one sporting a large oval soaking tub with a view.

    Daniel Petroni

    Outdoors, the grounds host a covered terrace ideal for al fresco entertaining, a barbecue area and lap pool embellished with fire features; and rounding it all out are a Crestron smart-home system, full-home generator and two attached garages with room for four vehicles, plus access to a residents-only beach club that has its own private marina.

    No stranger to the South Florida real estate market, Leonhardt also flipped two neighboring waterfront homes on Miami Beach’s Hibiscus Island in 2021 for an impressive $27 million.

    The listing was held by Chad Carroll of Compass; Brady Thrasher of Re/Max repped the buyer.

    Click here for more photos of the Laguna Drive estate.

    Daniel Petroni More

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    Rick Ross Just Dropped $35 Million on a Waterfront Mansion on Miami’s Star Island

    Rick Ross may have a track entitled “I’m Not a Star,” but he is the newest resident of Miami’s Star Island.

    Last month, it was reported that The Boss had his eyes on a waterfront estate on the exclusive island, and this week, the “Hustlin” rapper officially closed on the residence in question. Rozay threw down a whopping $35 million for the 40,000-square-foot mega-mansion that’s located near the middle of the star-studded and guard-gated enclave. From Diddy to billionaire Ken Griffen to Jennifer Lopez and Gloria Estefan, scads of high rollers maintain opulent abodes here. And, with only 30 homes on the island, it’s pretty impressive that the record exec was able to snag himself a coveted piece of the Star Island pie.

    “We are so excited to have hit a high note in finding the right buyer for this spectacular property so quickly after listing it,” said Jill Eber of The Jills Zeder Group, who represented the seller alongside colleagues Jill Hertzberg, Felise Eber, and Fabio Lopes. “There is only one Star Island, and we know the buyer will be so happy with his new residence on the much-sought-after island.” Kimberly Knausz with ONE Sotheby’s International Realty and Tawanda Roberts of Florida Realty of Miami represented Ross.

    Rapper Rick Ross just dropped $35 million on a mansion on Star Island in Miami

    The Jills Zeder Group/1 Oak Studios

    “He instantly fell in love with the grand entry, it has a very long driveway stretching towards the mansion that creates an air of real luxury,” added Knausz. “The architecture also played a part as it’s far beyond the ordinary modern home and he plans to enhance it to reflect his personal style.”

    The 12,374-square-foot spread offers up six bedrooms and nine bathrooms, plus a generous 100 feet of water frontage on Biscayne Bay. Currently, there’s a two-car garage on-site, but the Maybach Music Group founder will need way more room than that to fit all of his prized cars. And, when he decides to travel by boat, there’s a 40-foot dock equipped with an electric and water pedestal. Maybe he’ll get that Lamborghini yacht after all—if he hasn’t already.  

    The waterfront estate has views of the ocean and Biscayne Bay

    The Jills Zeder Group/1 Oak Studios

    The record exec is known for throwing his fair share of celeb-laden parties, so the spacious swimming pool, outdoor kitchen, and massive stone terrace should definitely come in handy. Inside, the two-story estate is decked out with a glass-enclosed foyer, a living room with 30-foot ceilings and a custom mahogany fireplace, a media room, and a library. Nearby, the chef’s kitchen is outfitted with granite counters, top-of-the-line appliances, a butler’s pantry, and a separate breakfast room.

    Ross clearly has a taste for the finer things in life so, naturally, the primary suite is fit for rap royalty. Think remote-controlled shutters, a wet bar, two walk-in closets, and dual marble bathrooms.

    Click here to see all the photos of Rick Ross’s Star Island mansion.

    The Jills Zeder Group/1 Oak Studios More