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David Gebbia, CEO of Gebbia Media and co-CEO of Big Machine Rock, just sold his Palm Island home, setting a new benchmark for a dry-lot sale on the exclusive Miami Beach island. He bought the property at 254 Palm Avenue for $5.4 million in late 2021. Roughly four years later, he walked away with a few million more. It’s a tidy return on its own, but that single deal is just one beat in a much longer Florida story.
Over the past several years, the Gebbia Family, the New York family behind New York Stock Exchange-listed Siebert Financial Corp. (NASDAQ: SIEB) and several other businesses during the last 30 years, has poured more than $50 million into South Florida real estate. The portfolio spans Miami Beach, Fort Lauderdale, and Boca Raton, with at least seven disclosed transactions across Palm Island, Hibiscus Island, Rio Vista, and South Beach.
By then, the Gebbias were already established in the market, having begun with David’s 2018 investment in three condos in the Ritz-Carlton in Miami Beach, soon followed by family patriarch John J. Gebbia and other family members in October 2020, with a Fort Lauderdale home at 500 Desota Drive for $7.9 million. From there, the family’s footprint expanded steadily: David’s Palm Island purchase in late 2021, the family’s South Beach office acquisition in January 2022, and a flurry of additional deals by his twin brother, Richie Gebbia, Co-CEO of Muriel Siebert & Co., throughout that spring.
Anchoring the family’s commercial portfolio is 653 Collins Avenue in Miami Beach. Bought for $6.8 million in January 2022, the 12,000-square-foot former retail space was retrofitted into the Florida headquarters for Siebert Financial and its subsidiaries, including Gebbia Media and its sports division, as well as rock label BMR. Today, it is valued between $15 and $18 million, with rare Miami Beach air rights that allow for further vertical expansion. Inside, the space breaks from financial industry convention with a built-in podcast studio, event space, and full bar at the center of the office; a rare sight for a financial firm, but a choice that makes Siebert stand out.
Richie Gebbia, co-CEO of Muriel Siebert & Co., paid $7 million in February 2022 for a waterfront teardown at 1025 North Rio Vista Boulevard in Fort Lauderdale, a 1-acre property on the New River with direct boat acces, a 150-ft. docking space and plans for a new spec mansion. Once the works are completed, its value is estimated to surpass $30 million. Two months later, he picked up a 4,500-square-foot non-waterfront spec house at 112 West Palm Midway on Hibiscus Island for $6.5 million.
The timing matters. Most of these deals landed before Miami’s Wall Street rush fully kicked into gear. Ken Griffin’s Citadel didn’t announce its Miami headquarters move until June 2022, five months after the family closed on their South Beach office. Stephen Ross’s “Florida Gold Coast” push and the Ambition Accelerated campaign came later. David’s Palm Island exit is far from a farewell. He is now looking for his next home in Miami, while the Gebbias continue expanding their residential and commercial holdings across the region.
And there are already signs of what comes next.
In March 2026, Siebert added an office on Fort Lauderdale’s Rio Vista waterfront, deepening its wealth management presence across the region. The Gebbia Family is now actively looking to buy a property to firmly establish Siebert Financial and their holdings in the city.
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