
The Windsor was a Chrysler staple throughout the 1940s and 1950s. When Chrysler rolled out the first round of its “Forward Look” products in 1955, it applied the Nassau name to an entry-level Windsor 2-door hardtop. It was a one-year offering. Nearly 18,500 copies were built that year, yet when was the last time you saw one? This project has bad floors but reportedly has good exterior sheet metal. Located with a dealer in Redmond, Oregon, this once-mighty Mopar is available here on craigslist for $4,500.

In 1955-56, Chrysler had some of the boldest-looking cars on the market. They ramped up the effort in 1957-59, and bold turned into wild with some of the craziest tailfins of the era. This ’55 edition of the Windsor Nassau Deluxe was probably quite the looker back in the day, with one of the most aggressive front ends on the market. Under the hood, a 301 cubic inch “Poly” V8 called the shots, though the engine in the seller’s car isn’t confirmed as original.

We suspect this Chrysler has been on the back burner for several years. It doesn’t run, so dormancy is probably mechanically related at north of 100,000 miles. But the photos provided by the seller show a bad case of rust in the floorboards and probably the trunk. The seller proposes the buyer do a body swap, but would that be more trouble than welding in some new pieces to the chassis?

If you’re a fan of Virgil Exner automobiles, this Windsor is a classic example of his work. He became head of design at Chrysler in 1953, so he certainly would have had a heavy hand in the development of these cars. If the sheet metal is as good as the seller says, and the chrome bits look great, would you invest the time and money to restore this one? Thanks for another cool tip, “Curvette”!


That’s a 331 Hemi not a Poly.I like the 55-56 alot more than the huge fin 57-and beyonds :P
Yes, Hemi. Where did the 301 poly thought come from?
That should be the base motor…..through the years the Windsor would get the poly instead of the Hemi as base….
My family had a 1956 2 door like this one back in the mid 1970’s when I was about 5 years old faded red with a white roof back in NJ. My Dad told me year later that the exhaust and maniflolds were rusted bad and sold it for 300 dollars to his local mechanic shop owner for the demo derby.
If it is the correct engine, it would be a 331 Hemi!
Gotta be a Hemi. Spark plugs through valve covers is a certain giveaway. 331I believe.
It’s not a crazy price for this 55 Chrysler roller, non running Windsor. It’s a good starting point for an entry level project. And at this price, it won’t break the bank.
The base engine in the base Windsor line was a Poly motor…..
Nice looking Chrysler! Much better looking than how they closed out the decade. And yes a hemi under the hood. This would be a great project to get up and running. Clean it up, patch as necessary and get it road worthy.
Love that front end.
Could make a good C 300 clone if someone wants to put in the effort.
I’d pass. If you like these the one to buy is the New Yorker Deluxe St. Regis. You’ll put exactly the same money into restoring this one but it won’t be nearly as valuable when you are done.