Chrysler Windsor

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.

Prices range from $1,000 for projects to over $35,000 for pristine, show-quality examples.