Classic Chrysler Windsor for Sale

18 listings

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18 listings found From $6,000 to $74,950

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1956 Chrysler Windsor

$22,500 $25,900

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Recently Sold Chrysler Windsor

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Vehicle	Sold For	Date
1950 Chrysler Windsor	$13,495	Apr 2026
1949 Chrysler Windsor	$39,900	Jan 2026
1956 Chrysler Windsor	$25,900	Dec 2025
1948 Chrysler Windsor	$27,895	Nov 2025
1948 Chrysler Windsor	$24,995	Sep 2025
1950 Chrysler Windsor	$15,295	Sep 2025

Frequently Asked Questions about the Chrysler Windsor

Based on listings on Classic Cars Arena, the Chrysler Windsor appears in years 1947–1962. We currently have 12 Chrysler Windsor listings spanning these years.

Agreed-value classic car insurance for a Chrysler Windsor typically runs $300–$1,200 annually, depending on stated value, mileage limits, and storage conditions. Hagerty, Grundy, and American Collectors are common providers for vintage policies.

Many classic Chrysler Windsor examples have notable provenance — celebrity ownership, racing history, or movie/TV appearances add significant value. Documented history (signed titles, magazine features) can multiply a vehicle's value by 2–5x.

Performance enthusiasts gravitate toward the V8 for its balance of power and reliability. Among 12 listings, V8 examples are most actively traded, indicating strong demand.

Full body-off restoration of a classic Chrysler Windsor typically costs $25,000–$80,000+ depending on condition starting point, parts availability, and labor rates. Mechanical-only refresh runs $5,000–$15,000. Always factor in unexpected discoveries during teardown.

Reversible upgrades (electronic ignition, modern A/C, audio) generally don't hurt value. Irreversible mods (cut-up bodywork, non-original engines, painted-over trim) reduce collector value. Original numbers-matching examples command 20–40% premium over modified ones.

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