How Trump's sprawling beachside 11-bedroom estate, for sale at a reduced price of $16.9 million, managed to avoid damage when so many other estates nearby were seriously or catastrophically ruined is unknown, Fleishman told USA Today.
President Trump's $17 million Chateau des Palmiers on the French Caribbean island of St. Martin survived Hurricane Irma.
USA Today has reached out to the Trump Organization for comment.
Meanwhile, the fate of Trump's other major property in the path of Irma, his Palm Beach Mar-a-Lago resort-turned-winter White House, remains up in the air.
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But the expectation is that it, too, will suffer little damage, having survived multiple hurricanes in the 90 years since it was built on an island between the Atlantic Ocean and Florida's Intercoastal Waterway. Besides that, Irma veered more to the west as it moved up the Florida peninsula.
The same can't be said about the Caribbean properties of other celebrities affected by Irma, though the status of some remains unknown.
So far, there's no word on any damage to luxury homes owned by Gloria Estefan and Sean "Diddy" Combs on the star-studded Star Island, a man-made retreat off Miami Beach. Nor is it known how Johnny Depp's private Little Hall's Pond Cay or Eddie Murphy's private Rooster Cay in the Bahamas fared. Or Oprah Winfrey's Caribbean getaway mansions on Antigua and Paradise Island in the Bahamas.
But some other celebrity owners of Caribbean islands and properties have gone public with their losses.
British billionaire Richard Branson of the Virgin empire posted pictures online of his private Necker Island in the British Virgin Islands, which was nearly destroyed by the hurricane while he and his staff rode out the storm in a concrete wine cellar.
"We felt the full force of the strongest hurricane ever in the Atlantic Ocean," he wrote. "But we are very fortunate to have a strong cellar built into Necker's Great House and were very lucky all of our teams who stayed on Island during the storm are safe and well."
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Now he's raising money for a disaster recovery plan for the BVIs.
Tiny Barbuda, one-half of the dual state of Antigua and Barbuda, was flattened by Irma. Most of the island's residents are homeless.
Robert De Niro, a co-owner of the Paradise Found Nobu resort under development on Barbuda, issued a statement to the New York Daily News saying he was "beyond saddened" by the Barbuda devastation and vowed to "rebuild what nature has taken away from us."
Milo Yiannopoulos, the right-wing journalist/provocateur whose speeches roil campuses and whose remarks seeming to condone sex between men and boys forced him to resign from Breitbart, posted on his Facebook page Sunday that his house in the West Brickell area of Miami is "gone."
This post came after Yiannopoulos joked last week on Facebook about "positive Irma news" in describing how Branson's Necker Island had been devastated. A representative for Yiannopoulos hasn't responded to USA Today's request for comment about his Miami house.
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But good news: The historic Hemingway House museum on Key West survived with little damage, according to general manager Jacque Sands, who spoke to The Orlando Sentinel.
The personnel are safe, as are all 54 of Hemingway's famous six-toed cats.
Associated Press reports were used in this article.