Leonardo DiCaprio has come a long way in 20 years. Leapfrogging from Romper Room and Friends to Hollywood A-Lister and, at the same time, acquiring a real estate portfolio that might make Ellen DeGeneres envious. Part of his collection: an L.A. home he bought in the 1990s from Madonna, a fabulous mid-century modern home in Palm Springs that was built for Dinah Shore he bought in 2014, and a $23 million Malibu home he grabbed in 2017. But all of his buys don’t stay in his portfolio – some are given as gifts to family members. In a very generous act, Leonardo recently purchased the Los Feliz home of Modern Family star, Jesse Tyler Ferguson, for his mother, Irmelin Indenbirken, for $7.1 million. A few years ago, he also purchased a Los Feliz home for his dad, George DiCaprio, for $4.9 million.