The 1949 model year was a milestone for Chrysler. The company celebrated its 25th anniversary in the automobile business, and it promoted its new lineup as the Silver Anniversary models. This 1949 Chrysler Windsor convertible is part of that celebration. Finished in cream with a brown convertible top, it features plenty of postwar Chrysler styling, including bright chrome, big whitewall tires, and distinctive rear-fender trim. The seller says it still wears its original paint, imperfections and all. It’s located in Eustis, Florida, and is listed for $10,000 on Facebook Marketplace.
The interior is another reason this Windsor caught my attention. The colorful red, green, and blue plaid seat inserts appear to be Chrysler’s optional Highlander upholstery, paired with contrasting brown trim. It is a distinctive combination, and the red steering wheel adds another splash of color. Highlander plaid was available on Windsor models, including convertibles, making this a particularly interesting feature if the upholstery is original to the car. The dashboard has a great period look, with a large central speedometer and plenty of bright trim. The exterior paint shows its age, with cracking and peeling in places and noticeable imperfections on the driver’s door and rear quarter panel.
Under the hood is Chrysler’s 250.6-cubic-inch flathead inline-six, rated at 116 horsepower in the factory specifications. It’s paired with the Prestomatic semi-automatic transmission, part of Chrysler’s Fluid Drive system. This is one of the car’s more unusual features. You still have a clutch pedal and column shifter, but you don’t have to work through every gear yourself. Select Low or High range, get rolling, and when the engine reaches the right speed, lift off the throttle. The transmission handles the upshift. High range was intended for ordinary driving, while Low provided extra pulling power. It’s an interesting piece of pre-automatic technology that gives this Windsor a personality beyond its good looks. Chrysler built 3,234 Windsor convertibles in 1949.
The seller reports approximately 34,000 miles, although the actual mileage is unknown. The car reportedly runs and drives, but a flatbed is recommended. It currently needs carburetor work, a rubber fuel line, an accelerator pump, and tires. The seller also reports earlier fuel system and transmission work, along with a new battery installed in February 2026. The title is in the owner’s name, and the Chrysler is being sold as-is. I’d be tempted to sort out the mechanical needs, preserve that original paint, and enjoy this Silver Anniversary convertible with its unusual Prestomatic setup. Have you ever driven a Chrysler with Fluid Drive?
Nice!!! You can see it’s been taken care of.
I have! Pops owned a 1952 Dodge with fluid drive and he taught me how to drive it. I liked it because I hated shifting and this was ALMOST an automatic.
This is a beautiful car. You know I love yellow convertibles, and this one with its wide whites is gorgeous. Although I would rethink that interior. We had a 1938 Pontiac sitting in one of the barns with a red plaid interior. Yuck!