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Donald Trump was born into the real estate business in 1946 in New York City where his father, Fred Trump, was a developer. Donald got a jump-start in the business while he was in college in the 1960s, working menial jobs at his father’s lower-middle class apartment complex in Cincinnati. In 1971, he moved back to New York City where he took over his father’s company, changing the name to The Trump Organization and eventually earning a reputation as a fast-rising real estate tycoon on hotel, condominium and casino projects.

Trump was only 35 in 1982 when he and wife, Ivana, purchased their first mansion, a 5.8-acre home on a peninsula in Greenwich, Conn., for $4 million. Always a family-oriented business, Ivana was also remodeling the Plaza Hotel in Manhattan in the early 1980s and was able to incorporate many of the same materials in the decoration of their new home, creating a residence dripping in gold leaf, elegant chandeliers and crown moldings. When they divorced in 1991, Ivana won the mansion in the property settlement. She sold the Greenwich home for $15 million in 1998, and the mansion’s new owners immediately began a renovation to tone it down to more livable neutrals, add tennis courts and a 4,000-square-foot addition that includes guest suites, a lap pool and a sauna. It is currently listed for sale at $54 million.

Originally built in 1939, the 19,773-square-foot Georgian Colonial-style main house and guesthouse have eight bedrooms, 13 baths, a three-story rotunda foyer with double grand staircase, formal rooms overlooking the pool, grounds and Long Island Sound, a home theater, a putting green, multiple terraces and patios, tennis courts and three fully-equipped staff apartments. Awaiting a new Greenwich billionaire resident, Donald Trump’s former Connecticut mansion comes packed with major additions, including six waterfront acres and private boat dock.

Listed for: $54 million

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