Porsche 356 Speedster- $75,000-$500,000
The first production automobile that came from Porsche, the 356 Speedster has a lot of history behind it. Despite its huge collectible value nowadays, to the point that even replicas are highly sought after, the Speedster was not the most luxurious vehicle on the market even at the time. A rather sparse car, it had one canvas top and sides, bucket seats with static backrests, and very little in terms of instrumentation inside. That said, the unmistakable visual appeal of the vehicle and its place in automobile history makes it well-sought after, indeed.