It’s only natural that Leonardo DiCaprio, an IRL Wolf of Wall Street/Jay Gatsby hybrid, has swapped real estate these past three decades as often as he switches girlfriends (all under 25, until recently). The Academy Award-winning actor-who once shared a raft in freezing waters with Kate Winslet and has been adored worldwide ever since his splashy Hollywood entrance with What’s Eating Gilbert Grape-currently owns properties in locations from California to New York to a private island in Belize. Casual.