Price: £25,935,000 [$34,439,035]

The history of the most expensive car in this list dates back to 1957 when the first out of four 335 S rolled out of production. The Ferrari with chassis number 0674 had its share of great drivers at its cockpit, including Peter Collins and Maurice Trintignant, who both piloted the car in sixth place in the 12 Hours of Sebring of the same year that the car was produced. Then, it finished second at the dreaded the Mille Miglia in the hands of Wolfgang von Trips. It was then upgraded to a 4.1-liter and set the lap record at the 24 Hours of Le Mans, finished fourth in the Swedish GP, and second in the Venezuelan GP. It finally won the 1958 Cuban Grand Prix with Stirling Moss behind the wheel.

With a lot of wins under its belt, partnered with rarity and history, the Ferrari 335 S deserved its price when it was sold in 2016.