12: 1966 Chevrolet Corvette – $60,000
The C2 Corvette is undoubtedly the one that broke the mold. This was the Corvette model that introduced the world to the high-performance ‘Vette models we have today. The sheer design of the car was beautiful and the split window was even better looking. But the 1966 Corvette is way overpriced for what it is (via Work & Money).
Sure, it’s a classic, but that doesn’t justify almost being as much as a house. These older Corvette models had many reliability issues and replacement parts are hard to come by and expensive.