Chrysler Windsor
Positioned as Chrysler's mid-range model, the Windsor is best known for its dramatic 'Forward Look' tailfins from 1955. It's an accessible entry for collectors wanting an iconic car from the late-50s.
Chrysler Windsor sold for a median of $10,555 over the last 12 months, based on 8 auction sales; the middle 50% sold between $5,788 and $15,938. 43 currently for sale.
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Chrysler Windsor prices by year
| Year | Median (3 yrs) | Middle 50% | Sales (3 yrs) | For sale now |
|---|---|---|---|---|
| 1939 | $16k | – | 1 | 0 |
| 1940 | $17k | – | 1 | 3 |
| 1941 | $12k | – | 1 | 1 |
| 1942 | $118k | – | 1 | 1 |
| 1947 | $22k | $21k–$25k | 5 | 4 |
| 1948 | $6.6k | $1.1k–$7.8k | 5 | 3 |
| 1949 | $6.6k | – | 1 | 6 |
| 1950 | $7k | – | 3 | 2 |
| 1951 | $11k | – | 1 | 0 |
| 1953 | $1.9k | – | 2 | 0 |
| 1954 | $15k | – | 1 | 1 |
| 1955 | $11k | – | 2 | 7 |
| 1956 | $2.8k | – | 1 | 5 |
| 1957 | – | – | 0 | 3 |
| 1959 | $31k | – | 2 | 1 |
| 1960 | $9.2k | – | 1 | 0 |
Auction sales in the last 3 years; prices leave out salvage and other branded titles.
Listings
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.
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.
304 Chrysler Windsor vehicles have been tracked across auctions and listings on Hypercars, with 43 currently live.
Data sourced from auction results and dealer and private listings, including Bring a Trailer, Cars & Bids, Mecum, RM Sotheby’s and eBay Motors. Updated daily.
Frequently Asked Questions
How much does a Chrysler Windsor cost?
Over the last 12 months, Chrysler Windsor sold for a median of $10,555 across 8 auction sales tracked on Hypercars; the middle 50% sold between $5,788 and $15,938. There are 43 currently for sale.
How many Chrysler Windsor listings are for sale right now?
There are 43 Chrysler Windsor listings currently live across auctions, dealers, and marketplaces tracked by Hypercars.