1. 1957 Ferrari 250 Testa Rossa
This same model was previously 6th on this list of the most expensive cars ever sold at auction, and with a number of other vintage Ferrari’s on the list, it was just a matter of time before the price was ratcheted up even higher. This particular car is quite rare, as one of only 32 ever made (from 1956-1961), a participant of the 1957 24 hours of Le Mans, and a winner in Buenos Aires and Sebring formula One events. Showing just how good of an investment classic cars can be, this exact car was bought for $12.2 million in 2009. The car is unrestored, but appears practically new thanks to it long being held by the Henry Ford Museum outside of a Detroit, where the experienced Henry Ford team kept it in pristine condition. In 2014 the car was sold for an insane $39.8 million.