Estimated high price: $3,410,000
The 911 is, overall, the most successful sports car-turned-race car in the world, having won virtually everything there is to win. This 911 GT1 Evolution, though, is different. It was designed as a race car first, to get around the rules, then carefully adapted to be street legal. Even by the most tightly scrutinized definition of the term, this is the "street-legal race car" archetype.
This exact car competed in the 24 Hours of Daytona, then won a bunch of races in Canada, no doubt aided by the "600+" hp lurking between the driver and the rear wheels... and it's absolutely legal to drive down the street today.
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Aaron Miller is the Cars editor for Thrillist, and can be found on Twitter. He's still crazy about the Alpine A110.