In 2004, as part of the bankruptcy, the property went up for auction. Mr. Trump topped at least two other bidders with an offer of $41.35 million. After the sale, he told The Palm Beach Daily News that he would turn the estate into the “second-greatest house in America,” after his Mar-a-Lago home down the road. He would then sell it to “create terrific value.”

The extent of Mr. Trump’s improvements after the purchase remain unclear. Mr. Trump initially said he had “gutted the house” and made $25 million in extensive renovations. Yet in the application for demolition, filed in February, the architect for the project said that the 2005 and 2006 renovations were limited to a new kitchen, the creation of new bedrooms and bathrooms, and “some minor interior alterations of doors, frames and windows.”

Mr. Trump put the home on the market in 2006 for $125 million, making it the most expensive listing in America at the time. When no buyers emerged and Mr. Trump replaced several brokers, he trimmed the price to $120 million.

Image Dmitry Rybolovlev, photographed last year at his apartment in Monaco, bought the Maison de l’Amitié, in Palm Beach, Fla., from Donald Trump in 2008 for $95 million, making it the most expensive single residential property ever sold in town. Credit... Benjamin Bechet for The New York Times

In the summer of 2008, just before the real estate market crashed, Mr. Trump found his buyer: Mr. Rybolovlev, a former medical student who took his fertilizer company public in 2007 and later moved to Switzerland and Monaco. He had toured several homes in Palm Beach but hadn’t found what he wanted.

“I showed him five big oceanfront homes,” said Carol Digges, a real estate broker representing Mr. Rybolovlev at the time. “But he said, ‘I want something more grand, something bigger.’” When she showed him Maison de l’Amitié, Mr. Rybolovlev was impressed and eventually negotiated a deal. Mr. Trump maintains he sold the property for $100 million, yet people involved in the deal, as well as the sales deed, put the price at $95 million.

At the time, Mr. Rybolovlev said he bought the property as an investment. “This acquisition is simply an investment,” he said in a statement and “does not represent a decision by me to live in the U.S.”