£52.3 million – Sold recently to WeatherTech CEO and famed Ferrari collector David MacNeil in a private deal, this 250 GTO is one of two GTOs on this list and one of five 250s. This particular car has one heck of a history.

Winner of the 1964 Tour de France car race, a year earlier it finished fourth at Le Mans too. The car hasn’t even been crashed despite the fact it’s been used, and used well. That bumped the price up even further.