Chrysler does not build many cars like the Chrysler Windsor with 241.5 CID Chrysler I6, built from 1939 to 1966 when streamlining and independent suspension were arriving together.
Where it came from
The Chrysler Windsor is a full-size car which was built by Chrysler from 1939 through to the 1960s. The final Chrysler Windsor sold in the United States was produced in 1961, but production in Canada continued until 1966. The Canadian 1961 to 1966 Windsor model was for all intents and purposes the equivalent of the Chrysler Newport in the United States. The Windsor was almost identical to the more luxurious Chrysler New Yorker in terms of size, interior and standard features except that it was only available with the Chrysler Straight Six that originally started the company in 1925, which offered customers a luxurious car with a more modest and economic engine.
As the years progressed and technology and manufacturing costs improved, the Windsor offered items that were initially optional as standard equipment while maintaining a market position lower in the Chrysler product hierarchy. The Windsor was mechanically similar to the Royal from 1939 to 1950 and offered more standard equipment and an upscale interior to the well equipped Royal while both vehicles came with the Chrysler Straight Six. As the Royal nameplate was discontinued for the 1951 model year the Windsor became Chrysler's six cylinder coupe until 1955 when the Poly V8 was introduced. For the 1961 model year the Chrysler Newport assumed the market position originally held by the Royal, keeping the Windsor positioned one level above the Newport. Chrysler replaced the Windsor name in 1962 with the introduction of the non-lettered series Chrysler 300.
Under the skin
Under the skin sits 241.5 CID Chrysler I6. The gearbox is a 3-speed manual. The layout matters: a front engine drives the rear wheels, the classic proportion — long bonnet, cabin set back — that most people picture when they picture a sports saloon or a grand tourer. The wheelbase is 119 in (1939) / 122.5 in(1940-42) / 139.5 in (1940-42). These are manufacturer figures carried by Wikipedia and Wikidata, not road-test measurements.
In context
Where it sits in Chrysler's history is not in doubt: the Chrysler Royal came before it; the Chrysler Newport followed it; it was built at Jefferson Avenue Assembly. On a showroom list of its day it stood against the Lincoln Continental, the Volkswagen Beetle, the GM (General Motors) Bedford OY. Nearby in the Chrysler catalogue sit the Chrysler Falcon and the Chrysler Chronos.
The money
MotorJury scores cars on the United States complaint and recall record, and the Chrysler Windsor has none: too old, too rare, or never sold there. Its value today is a collector's question, decided by provenance and condition rather than by a class average.