10 Expensive Vintage Sports Cars

The inductees on our list of 10 expensive vintage sports cars had to meet certain criteria. They had to look cool. They had to be fast. Finally, they had to cost a small fortune. Coolness knows no monetary limit. Without further ado, listed by price our picks are:

  1. 1953 Chevy Corvette. You simply have to love America’s first sports car. Considering the car started as just an experiment for a car show, and was given its name by the All-American Soapbox Derby founder, you gotta admit, it’s a fine piece of machinery. Compared to the rest of the cars on our list of expensive vintage sports cars, it’s a steal at around $200,000.
  2. 1967 Lamborghini 400 GT 2+2. Originally designed from the 350GT prototype, what became the 400 GT 2+2 sacrificed some power. Even going from 360 hp to 320 hp, the 4-liter option was still impressive. Only 23 cars ever saw the light of day, and for just $250-350,000, you could own one of these rare expensive vintage sports cars.
  3. 1956 Jaguar D-Type Sports Racer. It looks like it has a jet pack in the rear, suggesting this particular Jag might shoot flames on take-off. However, according to the most recent sale in 2010 by Gooding & Company, this expensive vintage sports car could set you back more than $3.7 million.
  4. 1964 Aston Martin DB5. It’s the James Bond car. Need we say more? If you have a cool $4-5 million to blow, one of these rare gems can be yours.
  5. 1966 Shelby Cobra 427 Super Snake. Aside from holding the record for the most expensive vintage sports car made in America, this baby boasts 800 hp. Eight hundred! And since there are only two in existence, it’s not surprising this beauty sold for $5.5 million in 2007.
  6. 1937 BMW 328 Mille Miglia. This was BMW’s very first sports car. It set the standard for other sports cars. Surprisingly, this beautiful example of expensive vintage sports cars only had 80 hp, a measly 2-liter inline 6, and could barely break 100 mph. At $5.84 million for the last model auctioned in 2007, it’s more cool than fast.
  7. 1933 Alfa Romeo 8C 2300 Monza. In 1933, having 178 hp, a 2500+ cc inline 8 with supercharger meant you were ready to race. When it comes to expensive vintage sports cars, paying nearly $7 million doesn’t sound so bad when you consider each of these cars were handmade.
  8. 1929 Mercedes-Benz 38/250 SSK. With a frame designed by Ferdinand Porsche, in its day, the Mighty Mercedes, as it was dubbed, was the fastest sports car in the world. Many collectors of expensive vintage sports cars consider this gem to be something of the Holy Grail. If you want one, look to spend $7.4 million or more for the privilege.
  9. 1962 Ferrari 330 TRI/LM Testa Rossa. This automotive icon has topped the list of the world’s most expensive vintage sports cars twice in the last decade. At 355 hp, it is the one and only 4-liter Testa Rossa model ever built. In terms of race cars, it's legendary, even today. Owning one will set you back a staggering $9.29, according to the most recent auction in May, 2007.
  10. 1961 Ferrari 250 GT SWB California Spyder. This particular Ferrari tops the list for being the absolute most expensive vintage sports cars sold at auction, ever. It’s also the infamous car from “Ferris Bueller’s Day Off.” James Coburn’s V-12, 280 hp 250 GT sold at the Ferrari museum in Italy for $10,894,000. Now where did we put that checkbook…
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