On the Market Since: 2015
Total Area: 9,535 square feet
Initial Value: $30 million*

Jeff Bridges, star of famous movies like The Big Lebowski and The Last Picture Show, listed his Montecito mansion on the market for $30 million in 2015. That was a far higher price than what Bridges originally paid for it in 1994, which was $7 million. The enormous estate had amenities like vineyards, hiking trails, fruit trees, and an art studio.

The Mediterranean mansion also had an 1,800-square-foot guest house, a second (smaller) guest house, a recording studio, a movie theater, and a pond to swim in. Finally, after two years on the market, Bridges sold the property for $15.93 million, around half the asking price.