5. Oprah Winfrey and Drew Barrymore
Oprah has had a vast estate in Santa Barbara’s Montecito neighborhood for years. Comedians Steve Martin and John Cleese (of Fawlty Towers and A Fish Called Wanda) happen to live in the neighborhood, too. In 2011, Drew Barrymore decided to join the party, dropping $7 million on a 72-year-old Mediterranean-style estate. She did not stay there long, though. She sold it in 2013 at a slight loss.