1959 Chevrolet Impala Convertible – $470,000
There are certain models of the Impala that come to mind first when you think of classic cars. The 1959 model was special in its own right with a big powerful V8 engine and a nice attractive exterior styling. That was not the only thing that made the 59 Impala great. The car was also available in many body styles, which made it appealing to consumers (via Motor Trend).

1959 became a surprise hit with the classic car community. The value continued to rise for the car, and it can be expensive to get your hands on one. The aftermarket community for the Impala is great and there are a lot of upgrades that you can do to the car. The 1959 Impala was one of the most attractive cars of its era.