Whoopi Goldberg – Chelsea, New York, 2.25 million

Caryn Elaine Johnson, known professionally as Whoopi Goldberg, is an American actor, comedian, author, and television personality. At the early notice of her career, Whoopi purchased a Victorian-style home located in Berkeley, California. The vintage home was built in 1890 and is included a 1,455 square foot main house and a two-story cottage that once served as a barn. There are also five garages in case extra space was needed to house her likely fleet of vehicles. Goldberg purchased the pad in 1985 for an affordable $335,000, but she listed it for $1.275 million back in 2015. Whoopi made a major return on her investment when the Berkeley house sold for $2.25 million.