The Haroldyn House, Greenwich, Connecticut
Trump was only 35 when he and Ivana – his first wife – purchased his starter mansion, a 5.8-acre home on a peninsula in Greenwich for $4 million (in 1982).
According to the real estate site, this is Trump’s “first trophy mansion.” When Trump divorced Ivana in 1991, she kept this house as part of the property settlement. Public records show the home was last sold in 1998 for $15 million.