The Chrysler Windsor served as the brand's mid-range model for over two decades, positioned below the luxurious New Yorker. Initially powered by the dependable 'Spitfire' inline-6, it later offered optional Poly-head V8s. The Windsor truly hit its stride with Virgil Exner's 'Forward Look' styling in 1955, gaining dramatic tailfins and a lower, longer profile that defined late-50s American automotive design.
Collectors appreciate the Windsor as an accessible entry into 1950s car ownership. It offers much of the same visual impact as the more expensive New Yorker or 300 Letter Series cars but at a fraction of the cost. Two-door hardtops and convertibles are the most sought-after body styles, prized for their classic pillarless or open-air motoring experience. The extensive chrome trim and distinctive styling make them standouts at any car show.
The market for Windsors is modest, with an average price just under $10,000 based on recent sales. This suggests that driver-quality sedans and project cars make up the bulk of transactions. While top-tier restored convertibles can exceed $35,000, most examples remain affordable, making them a great value in the classic car world.
Buying Tips
- Rust is the primary concern. Thoroughly inspect the floor pans, trunk floor, rocker panels, and the areas behind headlights and taillights.
- The inline-6 and V8 engines are durable, but check for signs of coolant leaks or smoke from the exhaust. Ensure the PowerFlite or TorqueFlite automatic transmissions shift smoothly.
- Chrome trim and body moldings are extensive and expensive to replace. A car with complete, undamaged brightwork saves a significant restoration expense.
- Interior components like dash pads, upholstery, and specific trim pieces are not widely reproduced. Prioritize cars with complete and well-preserved interiors.
Prices range from $1,000 for projects to over $35,000 for pristine, show-quality examples.
290 Chrysler Windsor vehicles have been tracked across auctions and listings on Hypercars, with 43 currently live.
Data sourced from Bring a Trailer, Cars & Bids, eBay Motors, PCarMarket, and Collecting Cars. Updated daily.
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