Josh Flagg Lists Reimagined Mediterranean Villa on Miami Beach's Exclusive North Bay Road For $10 Million With Jordan Karp LLC

Flagg Family Capital, in partnership with Carolwood LP, has officially listed its newly rebuilt Mediterranean villa on North Bay Road for $10 million with Jordan Karp LLC, marking one of the most compelling non-waterfront offerings to hit Miami Beach this season. The home, developed by Josh Flagg who has starred on Bravo’s Million Dollar Listing Los Angeles, and redesigned by BuiltIN Studio / Gary Eisner, sits directly across from David and Victoria Beckham’s $72.5 million bayfront compound—placing it in one of the corridor’s most exclusive pockets.

The 4,000-square-foot residence is positioned on a lush 10,000-square-foot lot with a gated entry and resort-style grounds. Inside, vaulted ceilings, new custom wood flooring, bespoke millwork, and a restored limestone fireplace create a warm modern Mediterranean aesthetic. The kitchen features white oak cabinetry, SubZero appliances, and Waterworks fixtures, while the bathrooms showcase travertine accents and custom detailing throughout. A detached pool house functions as a private wellness retreat with a sauna, cold plunge, outdoor shower, and powder room.

Flagg has been clear that the timing of the listing aligns with shifting political sentiment in New York, which he says accelerated his decision to bring the home to market through broker Jordan Karp of Jordan Karp LLC.

“The minute New York elected Mandahmi, I called my broker Jordan Karp,” Flagg says. “I didn’t even wait for the acceptance speech.” Since going live for $10 million, the listing has already generated immediate attention from local, domestic, and international buyers—mirroring a larger post-election migration pattern toward tax-friendly, lifestyle-driven markets like Miami and Palm Beach.

North Bay Road itself remains one of the country’s most prestigious residential streets, home to a roster of global entrepreneurs, investors, entertainers, and legacy families. With multiple recent trades above $70 million—and several pushing past the $100 million mark—the corridor has become synonymous with scarcity, exclusivity, and record-setting land values. Inventory is minimal, and any newly finished product tends to move quickly. Flagg and Carolwood LP's property, headed by Adam Rubin and Andrew Shanfeld, is located across the street from David Beckham's $72.5 million compound on Biscayne Bay.

Flagg describes the home as “essentially brand-new,” with every system, finish, and layout refined during the renovation. Though he maintains a significant real-estate footprint in both Los Angeles and New York, he views this Miami project as part of a broader strategy to position capital in markets with strong momentum. The ongoing influx of Northeastern wealth, alongside interest from London, California, and Europe, has only reinforced that conviction.

“But let me be clear, I love New York. It’s home half the month. I spend two weeks there and two weeks in L.A., and I still own plenty of real estate between Manhattan and Long Island. I’m not changing anything in New York, I’m just taking advantage of what’s happening in Miami. It’s called business.” Said Flagg.

With the listing now active with Jordan Karp LLC, the property adds another high-profile chapter to North Bay Road’s ongoing luxury surge. And while Flagg developed the residence as an investment rather than a personal residence, he hints that Miami remains firmly on his radar.

“Florida’s fine, it’s not going anywhere,” said Flagg. “Once the noise dies down, I’ll probably just buy everything back again. I invest where it’s the right place at the right time. The only things I’m emotionally attached to are Los Angeles, New York, and zoning laws… and Florida’s been on a waitlist for all three since the 1980s.”

Images via Binyan Studio and Jordan Karp LLC

Former Los Angeles Dodgers-Star Alex Guerrero Lists Newly Built North Bay Road Estate For $75 Million

Former Los Angeles Dodgers-star Alex Guerrero has listed his newly built, waterfront North Bay Road estate for $75 million with Lourdes Alatriste of Douglas Elliman. One of the most architecturally ambitious and design-forward homes in Miami Beach — the iconic estate is located at 3100 North Bay Road, located on the prestigious Millionaire’s Row.

Alex Guerrero is a celebrated Cuban-born power hitter and former Los Angeles Dodgers standout, revered for his explosive performance on the field — including his stint as a Nippon Professional Baseball (NPB) All-Star and home run champion in Japan. Guerrero now offers a bold, one-of-a-kind residence that mirrors his dynamic global career.

The estate commands attention with its elevated design and rare architectural fluency. Conceptualized by Valle Valle & Partners and co-curated by LF Development LLC, the home is a study in elevated engineering and artistic vision. Spanning over 10,250 SF under air, the home features seven ensuite bedrooms, including a 1,500 SF primary suite with a private garden oasis. Inside, custom-crafted Italian cabinetry, couture-grade closets, and sculptural volumes set a dramatic yet fluid tone. Two designer kitchens — one for daily use and one fully equipped for catering — make the home ideal for both intimate living and large-scale entertaining.

The resort-style outdoors designed by landscape architect Vincent Filigenzi offers a lush, layered sanctuary with curated gardens, reflecting water features, and expansive entertaining terraces. A heated infinity-edge pool, hot tub, and cold plunge off the primary suite balcony overlook sweeping Biscayne Bay views. The home also features a fire pit, outdoor kitchen, 110’ of prime water frontage and an 80’ L-shaped dock designed to accommodate a 90’ yacht and jet skis.

For car enthusiasts, the home features an 18-car garage experience, including a 15-car undercarriage garage and a three-car air-conditioned garage above — an exceedingly rare feature that cements the home’s status as a true collector’s trophy. Sustainability plays a role, too — a solar-paneled roof supports eco-conscious living.

This exceptional property represents a singular opportunity to own a legacy residence at the crossroads of global sports stardom and cutting-edge design — right in the heart of Miami Beach’s most iconic stretch.

Renderings / Photos via REDVERTEX

North Bay Road Lot With 150' Of Waterfront Trades For $22.85 Million

One of the largest waterfront parcels in the prestigious estate section on Miami Beach’s North Bay Road just sold for $22,850,000 in a landmark transaction. Located at 5840 North Bay Road in Miami Beach, the vacant waterfront lot offers 150’ of unobstructed bayfront views, direct Miami skyline views, and a potential for a multi-structure legacy estate of up to 13,587 SF. Per public record the seller was Land Trust Services Corp TRS Trust NO 5840NBR. Cyril Matz with Douglas Elliman represented the buyer and Zachary Vichinsky with Bespoke Real Estate & Jill Hertzberg at Coldwell Banker Realty had the listing.

Image via Become Legendary

Barneys-Branded North Bay Road Estate Designed By Kobi Karp Sells For $40 Million In Off-Market Sale

A Barneys-branded waterfront residence designed by Kobi Karp on North Bay Road has sold for $40 Million in an off market deal. The seller and developer of the Barneys-branded estate is the Salter family which heads up brand-management company Authentic Brands Group, behind names like Reebok, Juicy Couture and David Beckham. Cyril Matz of Douglas Elliman represented the seller. The buyer, per public record, is consumer goods multimillionaire Anand Khubani, founder and CEO of Ideavillage Products, who made South Florida real estate headlines last year for a $100 million purchase of a La Gorce Island assemblage. The buyer worked with Evan Weiss of 305 Degrees Realty.

The custom home is a stunning showcase of Authentic Luxury Group’s yet-to-be-revealed Barneys New York Home Collection that will launch later this year. With interiors by Slim Keskes, creative director of Barneys Home, the masterfully curated waterfront residence features architecture by Kobi Karp and is nestled on a 30,800 SF lot with 100 feet of water frontage.

“This property was built as a custom home, not a spec home, so the materials and finishes were done at the highest possible level. They did not cut any corners,” said Cyril Matz of Douglas Elliman, who represented the seller. “Inventory is extremely limited on North Bay Road and this was the only home available of this caliber that was brand new construction, turnkey and had never been lived in. North Bay Road is one of the most in-demand addresses in Miami Beach because of its location, large estate size properties, incredible waterfront views and the high-profile neighbors.”

Showcasing 14,520 SF of interiors, the home features 6 bedrooms plus 2 staff rooms, a home office, movie theatre, full wellness center equipped with spa, sauna, steam, cold plunge and hot bath, a wine room, game room and rooftop accessible by elevator. The expansive outdoor areas feature 2 pools, one facing the water and another one facing east on the second floor. The home was fully finished with the highest quality materials and design, and sold completely furnished and accessorized.

Images via Kobi Karp for exteriors / Slim Keskes for interiors

Pair of Neighboring Estates On Miami Beach's Iconic North Bay Road Close For $30 Million

A pair of adjacent estates on Miami Beach’s North Bay Road, internationally known as “Millionaire’s Row,” have traded for $30 million. The North Bay Road properties, purchased by billionaire Richard Saghian, are directly across the street from one another and include a contemporary waterfront mansion and a lush Mediterranean villa.

5718 North Bay Road, which has 75 feet of frontage on Biscayne Bay, and 5725 North Bay Road, which is directly across the street, inland, sold to billionaire Richard Saghian, best known as the founder and CEO of fast-fashion company Fashion Nova. Saghian, who has an impressive collection of trophy homes, will continue to live full-time in Los Angeles, but plans to enjoy both Miami Beach residences as a vacation retreat. Saghian worked with Maurice Boschetti of Boschetti Realty Group, LLC.

The seller, Ami Shashoua, who owned both properties, worked with Berkshire Hathaway HomeServices (BHHS) EWM Realty’s Nelson Gonzalez. Shashoua’s successful career has involved work with financial institutions and tech companies, as well as real estate development and sales.

“Our tropical, tax-friendly market and rapidly growing economy continue to be a hotbed of activity…with these spacious, waterfront enclaves, in particular, being repeatedly singled-out by the globe’s one percent,” Gonzalez continued. “This buyer originally looked at this home 10 months ago, but we stayed on top of him. It took him a little while to recognize the opportunity he had to acquire one of the very few available modern mansions in this exclusive enclave.”

“Richard (Saghian) wanted a prime location and the best view of the skyline and open water – which can be a difficult feat,” said Boschetti. “He knew that the chance to own two luxury homes on coveted North Bay Road, taking full advantage of the ultimate Miami Beach lifestyle and views, was an opportunity that couldn’t be overlooked.”

From its tranquil, private setting along Biscayne Bay, the North Bay Road enclave has historically been one of South Florida’s most sought-after. Just this week, David and Victoria Beckham closed on a $72.25 million sale within the community at 4736 North Bay Road. Other high-profile neighbors, past and present, have included Cindy Crawford and Rande Gerber, Karlie Kloss and Joshua Kushner, and business owners Wayne Boich, Josh Harris, and Marcello Claure.

Each residence in today’s transaction has been a standout in its own right, but together, they have formed the quintessential Miami Beach haven.

Built in 2022, 5718 North Bay Road is marked by a magnificent, 15,536-square-foot lot with 75 feet of premier waterfrontage. Inside, seven bedrooms, eight baths, and two half-baths are spread throughout 7,767 square feet of lavish living space, while walls of glass complement the home’s open, sunlit floorplan. In addition to a wet bar, state-of-the-art theater, an elevator, a gourmet kitchen, wine cellar, interior fishpond with stingrays, gym, and rooftop terrace, the home has a cabana with a summer kitchen, saltwater pool with a spa, and an outstanding, oversized dock. Adding to its unmistakable draw, the dwelling is defined by unobstructed, postcard-worthy views of Biscayne Bay and dazzling sunsets over Miami’s skyline.

Across the street, 5725 North Bay Road is a recently remodeled Mediterranean-style villa with four bedrooms and four-and-a-half baths – punctuated by 3,167 square feet of airy living space. The home’s 8,550-square-foot lot, enveloped in verdant landscaping, is anchored by a sparkling pool and outdoor spaces for breezy alfresco dining and gatherings.

“It’s a combined total of 11 bedrooms, 15 baths, 11,012 square feet of living space, 24,086 square feet of land, and 75 feet of waterfrontage,” Gonzalez concluded. “The uniqueness of this offering cannot be overstated.”

Images via Luxhunters Productions

Waterfront Estate on North Bay Road Hits Market For $44 Million Listed With OFFICIAL's Oren Alexander

5050 North Bay Road, a classic post-modern design waterfront Miami Beach estate, has come back on the market for $44 million, down from a previously asked $49 million, and is now listed with Oren Alexander of OFFICIAL. The elegant North Bay Road estate was recently reimagined by Dara Huang, showcasing an air of timeless sophistication, meticulously crafted living spaces, six bedrooms, and seven bathrooms, that reflect South Florida living to its core.

Featuring breathtaking, unobstructed views of Downtown Miami and Biscayne Bay, 5050 North Bay Road is a 7,746 SF home located on an oversized 32,085 SF lot with 139’ of water frontage. The remarkable home is the perfect blend of modern luxury and classic elegance with sleek architectural details.

The open floor plan and large windows create a light-filled and welcoming atmosphere. Wood paneling throughout evokes a sense of warmth and coziness while impeccable detailing can be found in every room from the embroidered curtains and trimming to the furnishing and artwork. The kitchen features a large dining area, separate prep kitchen, breakfast nook, and a dedicated butler’s pantry with a rotisserie oven. The layout includes four bedrooms with the primary suite situated upstairs along with two additional rooms. The primary suite is a private oasis with a terrace overlooking the bay and spa-inspired bathroom with a sauna.

The guest house spans 1,500 SF and features two separate entrances that can be configured as four bedrooms – in its current state it is situated as two separate bedrooms with one living area each.

The outdoor living spaces are akin to a private resort, featuring perfectly manicured grounds adjacent to the wide-open views of Biscayne Bay and 139’ on the water complete with an oversized dock. A backyard pool offers an entertaining area with a covered pizza oven and grill. The pool on the side of the house boasts a steam and sauna, cold plunge and hot tub.

Images via OFFICIAL / DADA Goldberg

Witkoff Lists Waterfront North Bay Road Lot For $19.95 Million With Approved Plans For Kobi Karp-Designed Mansion

The iconic real estate investment and development firm, Witkoff, who recently announced Auberge Shore Club and is planning three mixed-use towers in Miami Worldcenter, has listed a waterfront lot on North Bay Road for $19.95 million. The property comes with approved permitted plans by star architect Kobi Karp, whose vision calls for seven beds, nine baths on the lot with 100 linear feet of west facing waters to indulge in Miami’s famous sunsets.

The tropical modern home design encapsulates South Florida’s tropics with lush greenery set to surround the perimeter of the home while walls of glass offer direct views of Biscayne Bay and indoor/outdoor living.

Offering impeccable design and expansive living spaces, the home design features a towering great room, multiple entertaining spaces, and dual waterfront lounges are just a few features within the versatile layout. Ample light is set to pour through the Primary and VIP suites that offer bayfront terraces with open water views. A show kitchen, a chef's kitchen, elevator, service room, and an office with a private entrance are also included in the floorplan.

The backyard is slated to feature an incredibly sleek 50’ resort pool and spa reminiscent of a tropical retreat, plus an indoor/outdoor gym, and a rooftop putting green with star-lit lounge area.

4766 N Bay Rd is listed for $19.95 million by Dina Goldentayer with Douglas Elliman.

Images via Legendary Productions/ Dina Goldentayer, Renderings via Douglas Elliman/ Dina Goldentayer and Kobi Karp

Former CEO of SoftBank Marcelo Claure Lists Vacant North Bay Road Lot For $39.9 Million Complete With Permitted Plans By Iconic Architect Kobi Karp

The former CEO of SoftBank, Marcelo Claure, has listed one of the largest and most spectacular waterfront vacant lots to recently enter the Miami Beach prime property market for $39.9 million. The property is listed with Berkshire Hathaway HomeServices EWM Realty Senior Vice President and top-producer Nelson Gonzalez and comes complete with fully permitted plans by renowned architect Kobi Karp.

Presented for $39.9 million, the listing, 5212 North Bay Road, is an expansive, 27,334-square-foot vacant lot – equating to $1,459 per square foot. The property offers 150 feet on Biscayne Bay, providing stunning, unobstructed panoramas of the Miami skyline, sunset, and Biscayne Bay. The vacant property’s availability is unique for the area, which currently has few, if any, empty lots for sale, and none comparable to this property’s size and scope.

The property comes with permitted plans by internationally revered architect Kobi Karp, whose vision calls for a nine-bedroom, 14-bath (eight full-bath and six half-bath) mansion with 14,000 square feet of lavish interiors, an abundance of amenities, and extraordinary exterior spaces, including a rooftop that has been positioned to capture the sheer magnitude and entirety of the views. A new seawall and dock are also currently under construction.

“This is a landmark opportunity for a savvy buyer who’s looking to build their waterfront dream home,” said Gonzalez. “For someone seeking a large piece of land with the best price and location, this listing cannot be overlooked. And because of Kobi’s permitted designs, a buyer can put a shovel in the ground on the day they close.”

Featuring a central and tranquil location, the property is additionally located within minutes of the La Gorce Country Club and golf course, beaches, the Sunset Harbour and Bal Harbour neighborhoods, downtown Miami, and the Brickell financial district.

Images via Berkshire Hathaway HomeServices EWM Realty

NBA Star Tim Hardaway Jr. Buys Non-Waterfront North Bay Road Home Built By Todd Michael Glaser For Record $9.15 Million

Todd Michael Glaser has broken the record on North May Road for most expensive non-waterfront single-family home purchased to date. NBA star Tim Hardaway Jr. closed on the newly developed 6015 North Bay Road for $9.15 million. Nelson Gonzalez of Berkshire Hathaway HomeServices EWM Realty represented the seller in the transaction.

The new contemporary luxury home on exclusive North Bay Road developed by Todd Michael Glaser with ultra-modern design and architecture by DOMO Architecture + Design. Situated on a large 9,371 SF lot, the home features a two car garage and driveway. The 4,684-SF home offers 6 bedrooms, 6 bathrooms and 1 half-bath. The downstairs features an open floor plan with open chef’s kitchen and living areas overlooking the lush pool areas. Upstairs offers an upper family room as well as 4 large bedrooms, including a lavish master suite taking the entire pool side of the house. Outdoors is finished with lush landscaping, 2 pools including a lap pool, covered porches, summer kitchen, and garden for ample space for outdoor living in Miami Beach.

Chris Bosh's Former North Bay Road Estate Sells To Crypto Industry CEO Of MoonPay For $38 Million

Ivan Soto-Wright, the co-founder and CEO of crypto payment system MoonPay, has acquired Miami Heat icon Chris Bosh’s former Miami Beach estate on North Bay Road for $38 million. MoonPay is a London-based online payment system for cryptocurrencies which just recently MoonPay hit a $3.4 billion valuation following a new $555 million funding round led by Tiger Global Management and Coatue. Albert Justo and Mirce Curkoski with The Waterfront Team at One Sotheby’s International Realty were the listing agents and Dina Goldentayer of Douglas Elliman represented the buyer. No comment has been made about the method and terms of transaction.

Bosh sold the same home in January 2021 for $14.4 million to AquaBlue Group, led by Philippe Harari, who would renovate the home before relisting it for $42 million and selling to Soto-Wright for $38 million. The massive price increase reflects the strong demand for waterfront real estate in Miami.

Upon arrival into the lushly landscaped property, guests will be greeted by a living green wall and a garden courtyard area with water installations that highlight the home's perimeter. The gut-renovated home features seven bedrooms and eight bathrooms, with wood and stone finishes throughout. The double-height great room is surrounded in glass, highlighting the captivating views of the bay and garden. Each corner of the home is intentionally and perfectly positioned to flow seamlessly together with high-end finishes from custom millwork to Italian marble slabs.

The grand master suite offers large closets, oversized bathroom with tub and dual sinks, morning kitchen and of course, stunning views. The kitchen features a custom Italian expansive chef’s kitchen with a huge island. The outdoors offers a mosaic tile infinity pool, a detached outdoor kitchen and cabana bathroom plus a separate guest quarters. The fully automated smart home also features a commercial-grade elevator and more.

Celebrity neighbors include Cindy Crawford and Rande Gerber, Karlie Kloss and Joshua Kushner, with former star owners including Dwyane Wade and Gabrielle Union. The home is seeking an overall record, but still lower price per square foot ($3,500) when compared to other recent sales like the sale of Phil Collins and Jennifer Lopez’s former home at 5800 North Bay Road which sold for $39 million at about $4,000 per square foot.

Imagery via ONE Sotheby’s International Real Estate