The 1950s saw the rapid advancement of the automobile. While many love styling that includes ample chrome and tail fins, those traits didn’t really show up until about 1955 across the industry board. Design evolved quickly, but so did performance and drivability, with things like automatic transmissions and power steering becoming more common. If you’re looking for a cheap classic car for sale, we found five from the 1950s that are certainly worth a second look.
1950 Chrysler New Yorker – $3,999

Located near Detroit, this Chryler has a roof tall enough for your hat. Seriously, not having to take your hat off was one of the most important parts of this car’s design. Talk about strange automotive history. In any case, this is a cheap ride, but no basket case. Featuring relatively fresh paint and a restored interior, it’s certainly eye candy. It appears to have a Spitfire straight-8, which would have made 135 horsepower. Plenty for then and now. Check it out here on Craigslist before it’s gone for good.
1954 Hudson Hornet – $9,500

For those seeking a little NASCAR fun, check out this classic Hudson Hornet for sale! It has the 308 flat head with Twin-H carbs! Yep, this was the tuner car of the 1950s, mostly thanks to Smokey Yunick’s tricks. It looks a little tired, but it seems to have been gone through and is ready for a new owner to enjoy. That’s exactly what this car needs, someone to drive it. This Hudson is a classic car for sale on Craigslist near Bellingham, Washington.
1955 Oldsmobile Super 88 – $6,000

The mid 1950s really saw a shift in automotive styling and power, and Oldsmobile was no different. Since its founding in the 19th century, Oldsmobile had always been a stable player in the marketplace. It kept that going with the redesigned 1955 88. This one is sporting the Rocket V8, supposedly original, according to the seller. It’s all there and ready for someone to shine it up! Find this classic Oldsmobile for sale on Craigslist near Milwaukee.
1958 Triumph TR3a – $10,000

Here’s something a little different. Triumph has played a significant role in motorsports history, and their cars for the roadway reflect that. This running and driving roadster has had signiicant restoration work done, as well as a few upgrades to make it more drivevable. Could this be a classic Miata alternative. If you’re near Houston, go check it. This Triumph TR3 for sale is on Craigslist here.
1959 Plymouth Savoy – $7,500

While it’s not Christine (1958 Fury), it sure plays the part. In storage for quite some time, this classic Mopar for sale is fresh out of the crypt and ready to rock. OK, it’s likely going to need a bit of work to make it totally roadworthy, but it’s a solid example and deserved of another chance. And if you’re not into the straight-6, you could always put a HEMI in it. This vintage Plymouth is for sale in southern California and can be found here on Craigslist.













