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Flagler Beach Blocks Oceanfront Home’s Proposed Vacation-Rental Conversion

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Florida Real Estate Market

Celebrities Flock to Florida’s Luxury Markets, Snapping Up Mega-Mansions

October 21, 2025
Luxury Florida mansion with waterfront view and palm trees.
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Florida’s most exclusive enclaves are witnessing a surge in high-profile real estate acquisitions, as celebrities and wealthy individuals are reportedly investing heavily in the state’s luxury property market. From the Florida Keys to the elite enclaves near Palm Beach, record-breaking sales are becoming the norm, signaling a robust demand for opulent waterfront estates.

Key Takeaways

  • Barstool Sports founder Dave Portnoy recently purchased a record-setting $27.75 million waterfront estate in the Florida Keys.
  • Manalapan, near Palm Beach, is seeing properties listed for significantly higher prices than their original sale values, with one mansion asking $134 million.
  • Fisher Island, south of Miami, boasts America’s most expensive zip code, with a median sale price of $9.5 million and a $500,000 membership fee for its exclusive club.

Record-Breaking Sales in the Florida Keys

Barstool Sports president Dave Portnoy has reportedly acquired a stunning waterfront compound in Islamorada, Florida Keys, for $27.75 million. This purchase sets a new record for the highest property sale in the village. The expansive eight-bedroom, 9.5-bathroom estate spans over 10,000 square feet and features amenities like private pools and a boat dock. Portnoy’s acquisition adds to his substantial real estate portfolio, which is estimated to be worth over $95 million.

Skyrocketing Prices in Manalapan

In Manalapan, a town known for its exclusivity and proximity to Mar-a-Lago, luxury properties are commanding astronomical prices. One waterfront estate is listed for an astonishing $134 million, five times its original sale price from 2013. This 22,355-square-foot mansion sits on 2.31 acres and offers dual waterfront access. The area is attracting ultra-wealthy buyers seeking privacy and luxury, with median list prices reaching $38.5 million. Other notable listings in Manalapan include a $285 million modern spec mansion and a $150 million Balinese-inspired estate.

Fisher Island: America’s Most Exclusive Address

Fisher Island, a secluded island south of Miami, has earned the title of the most expensive zip code in the United States. With a median sale price of $9.5 million, the island offers unparalleled privacy, accessible only by yacht, helicopter, or a dedicated ferry. The most expensive property on the island is a nearly 10,000-square-foot penthouse listed at $85 million. Beyond the property prices, residents must also pay a one-time equity membership fee of $500,000, plus annual dues of approximately $40,000, to access the island’s extensive amenities, including a private beach, numerous restaurants, and a state-of-the-art fitness center.

Sources

  • Barstool Sports founder Dave Portnoy buys record-setting $28 million waterfront estate in Florida Keys<!–
    –>
    , MarketWatch.
  • Megamansions in Florida’s Most Elite Enclaves Are Listed for Up to 5 Times Their Original Price, Realtor.com.
  • Florida island with America’s most expensive zip code has a $500,000 membership fee and homes up to
    $85million
    , Daily Mail.

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