Josh Flagg, one of the most recognisable faces in luxury real estate, will appear at AREC26, giving Australian agents the rare opportunity to hear directly from the broker whose career sales have surpassed US$3 billion.
Known for selling multimillion-dollar homes to celebrity clients, Josh’s own portfolio, valued at around US$50 million (AUD$72 million), shows how he invests when the deal is personal.
Expanding his LA footprint
His Los Angeles holdings include a mansion at 710 North Bedford Drive in Beverly Hills, purchased in 2022 for about US$8.4 million (AUD$12 million).
The roughly 7,100-square-foot property was reported by The Real Deal as part of Josh’s ongoing expansion in LA’s luxury market.
In 2024, he acquired a midcentury modern home in Trousdale Estates, Beverly Hills, formerly owned by singer Charlie Puth.
The 4,800-square-foot residence, built in 1965 and nicknamed the “de Cordova House” after former resident producer Freddy De Cordova, was purchased off-market for US$9 million (AUD$13 million) after reductions from its original US$17 million asking price.
Architectural Digest reported that renovations by architect Stephen Shortridge preserved the midcentury style while incorporating modern luxury touches.
Florida, Miami Beach’s Billionaires’ Row
In 2023, Josh expanded into Florida with a Mediterranean-style villa at 4727 North Bay Road, Miami Beach, for US$4.25 million (AUD$6 million), according to TMZ.
North Bay Road, nicknamed “Billionaires’ Row,” is home to David and Victoria Beckham, Michael Bay, and the Von Furstenberg family, with sales regularly topping US$70–100 million.
The 4,000-square-foot property, rebuilt from a 1930s structure, features vaulted ceilings, custom millwork, a restored limestone fireplace, travertine bathrooms, a spa-like primary suite, a pool with Baja shelf, and a detached pool house with sauna and cold plunge.
The home is now listed for US$10 million (AUD$14.4 million).
East Hampton, bi-coastal luxury
By 2025, Josh went bi-coastal with a Hamptons retreat in East Hampton Village.
The luxury broker, along with childhood friend and business partner Justin Gruenberg, purchased the six-bedroom traditional home for US$8.45 million, spending an additional US$150,000 on furnishings for a total of US$8.6 million, according to The NY Post.
The 4,400-square-foot residence includes 1,500 square feet of covered outdoor terraces and balconies. Sitting on half an acre, the property also features a pool, a pool house, and a garage.
Inside, a dramatic ‘great room’ boasts 38-foot accordion glass doors opening to a bluestone-floored porch with a fireplace, an automated screen, and an outdoor kitchen.
Palm Beach, shifting to ultra-luxury
Most recently, Josh appears to be reshaping his Florida holdings. While preparing to sell the Miami Beach home, he has reportedly gone under contract on a Palm Beach residence priced around US$9 million (AUD$13 million), reflecting a shift toward Palm Beach’s ultra-luxury market.
