1957 Ferrari 250 Testa Rossa – $39.8 Million

Next up is another rare racing classic, the 1957 Ferrari 250 Testa Rossa, or Ferrari 250 TR. Aptly named Testa Rossa, which means redhead, it is Ferrari’s second-most valuable car in existence. Only thirty-four redheads were manufactured, the most famous of which were made between 1957 and 1958.

As you might know by now, the Ferrari 250 TR is the rival of the Aston Martin DBR1. The two dominated the 1950s era, and the 250 TR only got ahead by an inch. This Ferrari got credit for winning ten World Sportscar Championships and three 24 Hours of Le Mans, among others. All these accolades boiled down to the Ferrari 250 TR being valued at at least $8 million. In 2011, one of these classics was sold at $16.4 million. Three years later, another one was sold for a whopping $38 million.