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Classic Chrysler for Sale Under $25,000

94 listings

Buy & Sell Chrysler Classics. New listings added daily.

Chrysler has been at the forefront of American automotive innovation since 1925. From the elegant 300 "Letter Cars" to the luxurious Imperial, classic Chryslers combine engineering excellence with bold style.

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94 listings found
1968 Chrysler Imperial Dealer
Texas

1968 Chrysler Imperial

$25,000
1965 Chrysler 300 Dealer
Texas

1965 Chrysler 300

$16,000
1974 Chrysler Imperial Dealer
United States

1974 Chrysler Imperial

$9,495 65,000 miles
1988 Chrysler LeBaron Dealer
United States

1988 Chrysler LeBaron

$9,995 55,379 miles
1977 Chrysler Cordoba Dealer
United States

1977 Chrysler Cordoba

$12,495 72,000 miles
1978 Chrysler Cordoba Dealer
United States

1978 Chrysler Cordoba

$15,495 73,651 miles
1947 Chrysler Windsor Dealer
United States

1947 Chrysler Windsor

$15,495 29,399 miles
1984 Chrysler LeBaron Dealer
United States

1984 Chrysler LeBaron

$21,495 87,624 miles
1968 Chrysler Imperial Dealer
United States

1968 Chrysler Imperial

$12,995 75,000 miles
1978 Chrysler New Yorker Dealer
United States

1978 Chrysler New Yorker

$18,995 69,000 miles
1964 Chrysler 300 Dealer
United States

1964 Chrysler 300

$18,995 72,000 miles
1986 Chrysler LeBaron Dealer
United States

1986 Chrysler LeBaron

$6,995 5,925 miles
1989 Chrysler 300B Dealer
United States

1989 Chrysler 300B

$12,495 69,257 miles
1968 Chrysler Imperial Dealer
United States

1968 Chrysler Imperial

$18,995 70,250 miles
1936 Chrysler Airflow Dealer
United States

1936 Chrysler Airflow

$17,895 47,017 miles
1964 Chrysler Imperial Dealer
United States

1964 Chrysler Imperial

$12,995 60,000 miles
1976 Chrysler New Yorker Dealer
United States

1976 Chrysler New Yorker

$16,895 25,000 miles
1964 Chrysler 300 Dealer
United States

1964 Chrysler 300

$11,395 104,000 miles
1929 Chrysler 300B Dealer
United States

1929 Chrysler 300B

$15,895 1,300 miles
1947 Chrysler Windsor Dealer
United States

1947 Chrysler Windsor

$12,495 1,000 miles
1951 Chrysler Windsor Dealer
United States

1951 Chrysler Windsor

$6,495 86,000 miles
1963 Chrysler Imperial Dealer
United States

1963 Chrysler Imperial

$14,495 90,000 miles
1964 Chrysler Newport Dealer
United States

1964 Chrysler Newport

$20,495 79,700 miles
1954 Chrysler New Yorker Dealer
United States

1954 Chrysler New Yorker

$23,995 108,000 miles

Frequently Asked Questions about Classic Chrysler

Reliability of a classic Chrysler depends heavily on age, prior maintenance, and originality. Pre-1980s mechanical systems are simpler and easier to service; later electronics-heavy models require specialty diagnostic tools. Regular use prevents rubber/seal degradation.
Classic Chrysler prices on Classic Cars Arena range from $3,700 to $87,995, with an average asking price of $19,864 across 81 active listings.
Export Chrysler variants often had different engines, emissions equipment, lighting, and trim to meet local regulations. Some export-only models are rare in the US market and can command premium prices when imported under the 25-year rule.
Most states grant classic/antique status to vehicles 25+ years old, including Chrysler models from that era. Specialized insurers (Hagerty, Grundy, American Collectors) offer agreed-value policies for classic Chrysler owners.
Value drivers: model, year, body style, engine, originality, condition, mileage, and documentation. Compare current asking prices on Classic Cars Arena, recent auction results (Mecum, Barrett-Jackson, Bring a Trailer), and Hagerty Valuation Tools for objective benchmarks.
Across 81 classic Chrysler listings, the most actively traded models are: Windsor, New Yorker, LeBaron, Imperial, Cordoba. These represent the brand's most recognizable and sought-after classics.
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Classic Chrysler Cars — Engineering Excellence

Walter P. Chrysler founded Chrysler Corporation in 1925, and the company quickly earned a reputation for engineering innovation. Chrysler introduced the first practical high-compression engine, the Hemi, and the first modern minivan, among dozens of other automotive firsts.

Most Popular Classic Chrysler Models

The 300 "Letter Cars" (300B through 300L) were America's most powerful production cars in the late 1950s and early 1960s. The Imperial represented Chrysler's ultimate luxury statement, while the New Yorker offered full-size prestige. The Newport and Town & Country provided stylish family transportation with premium appointments.