One of the top 35 highest grossing actors of all time, Matt Damon paid $10.3 million for this 11,331-square-foot abode in April 2005. Damon rose to fame after the success of the film Good Will Hunting, a screenplay he co-wrote and co-starred with friend Ben Affleck, for which the two bagged an Academy Award for Writing Original Screenplay and a Golden Globe Award for Best Screenplay. He went on to star in other award nominated films such as Saving Private Ryan, The Talented Mr. Ripley and The Departed, as well as in two movie franchises, the Ocean's series and the Bourne series.