29. 1962 Ferrari 250 GTO
Probably the most legendary, sought-after, and valuable classic Ferrari is the 250 GTO. The car was introduced in 1962 as the high-performance/racing version of the 250 series. The car was a separate model due to numerous changes to the engine and chassis. The 3.0-liter V12 delivered around 300 HP and the car was a winner on race tracks worldwide as a result of its power.

Only 36 cars were ever made in two distinctive series. The 250 GTO, although it was road legal, was practically a race car for the street. It cost over $20,000 new. But today if you want one, you might need to be a billionaire since the asking prices are over $45 million as a result of its rich history (via Ferrari). In fact, one even sold for a record $48.4 million in 2018, making this car a record-setting model because of its value (via Forbes).