Price: £18,214,976 [$24,187,630]

There were only five DBR1s ever made by Aston Martin, and this is the first of them. Aside from its rarity, it also has a winning bloodline, with this particular car winning the 1959 Nürburgring 1,000 km. Several known motorsport figures had a chance to race in this car, including Roy Salvadori, Stirling Moss, Jack Brabham, and Carroll Shelby, among others. Better yet, this car is maintained by Aston Martin specialists R.S. Williams.