Mecum Louisville (2019)

1955 Chrysler Windsor Newport Deluxe

RM Sotheby's Auburn Spring (2018)

1955 Chrysler Windsor Deluxe Sedan

GAA Early March (2018)

1956 Chrysler Windsor Newport

Mecum Los Angeles (2017)

1956 Chrysler Windsor Convertible

Mecum Portland (2016)

1955 Chrysler Windsor Convertible

1956 Chrysler Windsor

Chrysler Windsor - 5th Gen

Chrysler

Chrysler is an American automotive manufacturer founded in 1925 by Walter Chrysler. Long known for creating high end luxury cars, Chrysler is considered one of the &quot;Big Three,&quot; alongside General Motors and Ford. Over the course of its history, Chrysler has acquired and created brands such as <a href="https://www.classic.com/m/desoto">DeSoto</a>, <a href="https://www.classic.com/m/jeep/">Jeep</a>, and <a href="https://www.classic.com/m/dodge/">Dodge</a>, as well as itself being acquired first by Daimler AG, and then <a href="https://www.classic.com/m/fiat/">Fiat</a>. Notable models produced by Chrysler include the <a href="https://www.classic.com/m/chrysler/imperial/">Imperial</a>, <a href="https://www.classic.com/m/chrysler/new-yorker/">New Yorker</a>, <a href="https://www.classic.com/m/chrysler/300-letter-series/">300 Letter Series</a>, <a href="https://www.classic.com/m/chrysler/airflow">Airflow</a>, and <a href="https://www.classic.com/m/chrysler/cordoba/">Cordoba</a>. Chrysler was also responsible for the creation of the <a href="https://www.classic.com/m/imperial/">Imperial</a> brand, which was built by Chrysler, but branded separately in order to be marketed as an ultra high end car.

Chrysler is an American automotive manufacturer founded in 1925 by Walter Chrysler. Long known for creating high end luxury cars, Chrysler…

Windsor - 5th Gen

Chrysler Windsor

The Chrysler Windsor was introduced in 1939. The Windsor was a series of full size cars initially introduced above the entry level <a href="https://www.classic.com/m/chrysler/royal/">Chrysler Royal</a>. Starting in 1951, and for the vast majority of remaining production, the Windsor was Chrysler&#39;s lowest priced model. The Chrysler Windsor was built in seven generations: <a href="https://www.classic.com/m/chrysler/windsor/1st-gen/">1st Gen (1939-1942)</a>, <a href="https://www.classic.com/m/chrysler/windsor/2nd-gen/">2nd Gen (1946-1948)</a>, <a href="https://www.classic.com/m/chrysler/windsor/3rd-gen/">3rd Gen (1949-1952)</a>, <a href="https://www.classic.com/m/chrysler/windsor/4th-gen/">4th Gen (1953-1954)</a>, <a href="https://www.classic.com/m/chrysler/windsor/5th-gen/">5th Gen (1955-1956)</a>, <a href="https://www.classic.com/m/chrysler/windsor/6th-gen/">6th Gen (1957-1958)</a>, and <a href="https://www.classic.com/m/chrysler/windsor/7th-gen/">7th Gen (1959-1961)</a>. The Windsor would go on to be replaced by the <a href="https://www.classic.com/m/chrysler/newport/">Chrysler Newport</a>, although the Canadian market Windsor continued production until 1966, being a largely rebadged Newport.

The Chrysler Windsor was introduced in 1939. The Windsor was a series of full size cars initially introduced above the entry level Chrysler…

Windsor

The fifth generation of <a href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced for the 1955 model year. The fifth generation Windsor remained Chrysler&#39;s entry level model, and like all Chrysler&#39;s at the time, featured a dramatic redesign by Virgil Exner. This latest generation of Windsor was offered as a coupe, sedan, or convertible, and was fitted with Chrysler&#39;s 5.0L &#39;Spitfire&#39; V8 engine. Production of the fifth generation Windsor continued until 1956, when the <a href="https://www.classic.com/m/chrysler/windsor/6th-gen/">Sixth Generation Chrysler Windsor</a> was unveiled.

The fifth generation of Chrysler Windsor was introduced for the 1955 model year. The fifth generation Windsor remained Chrysler's entry…

Chrysler Windsor - 1st Gen

The <a href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced in 1939. Introduced alongside the Chrysler New Yorker, the Windsor was launched as a full size intermediate model. The first generation Windsor was available in a variety of sedan body styles, as well as convertible and coupe options. A 4.0L inline six engine powered the first generation Windsor, which was built until 1942, when production ceased for WW2. After the war, Chrysler would introduce the <a href="https://www.classic.com/m/chrysler/windsor/2nd-gen/">Second Generation Windsor</a>.

The Chrysler Windsor was introduced in 1939. Introduced alongside the Chrysler New Yorker, the Windsor was launched as a full size…

Windsor - 1st Gen

1st Gen

Chrysler Windsor - 3rd Gen

The third generation of <a href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced for the 1949 model year. The third generation Windsor was offered in sedan, coupe, convertible, and <a href="https://www.classic.com/m/chrysler/town-country">Town &amp; Country</a> station wagon body styles, as well as base, Deluxe, and Highlander trims. Third generation Windsor cars were fitted with a 4.1L inline six engine, and were in production until 1952, when the <a href="https://www.classic.com/m/chrysler/windsor/4th-gen/">Fourth Generation Chrysler Windsor</a> was introduced.

The third generation of Chrysler Windsor was introduced for the 1949 model year. The third generation Windsor was offered in sedan, coupe,…

Windsor - 3rd Gen

3rd Gen

Chrysler Windsor - 2nd Gen

The second generation of <a href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced for the 1946 model year. The second generation Windsor was largely similar to the previous generation due to WW2, but there were small improvements including a larger 4.1L inline six engine. This latest generation was available as coupes, sedans, and convertibles, and was built until 1948, when the <a href="https://www.classic.com/m/chrysler/windsor/3rd-gen/">Third Generation Chrysler Windsor</a> was unveiled.

The second generation of Chrysler Windsor was introduced for the 1946 model year. The second generation Windsor was largely similar to the…

Windsor - 2nd Gen

2nd Gen

Chrysler Windsor - 4th Gen

The fourth generation <a href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced for the 1953 model year. This new generation of Windsor was available as a coupe, sedan, or convertible, and was fitted with an enlarged 4.3L inline six engine. The fourth generation Windsor was only offered in Deluxe trim, and was built until 1953, when it was replaced by the <a href="https://www.classic.com/m/chrysler/windsor/5th-gen/">Fifth Generation Chrysler Windsor</a>.

The fourth generation Chrysler Windsor was introduced for the 1953 model year. This new generation of Windsor was available as a coupe,…

Windsor - 4th Gen

4th Gen

5th Gen

Chrysler Windsor - 6th Gen

The sixth generation <a href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced for the 1957 model year. The sixth generation Windsor featured redesigned bodywork, and was offered in sedan, coupe, convertible, or hardtop body styles, all fitted with Chrysler&#39;s 5.8L &#39;Spitfire&#39; V8 engine. Production of the sixth generation Windsor continued until 1958, when it was replaced by the <a href="https://www.classic.com/m/chrysler/windsor/7th-gen/">Seventh Generation Chrysler Windsor</a>.

The sixth generation Chrysler Windsor was introduced for the 1957 model year. The sixth generation Windsor featured redesigned bodywork,…

Windsor - 6th Gen

6th Gen

Chrysler Windsor - 7th Gen

The seventh and final generation of <a href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced for the 1959 model year. This final generation of Windsor was offered in hardtop, coupe, sedan, and convertible body styles. Power for the seventh generation Windsor came from a 6.3L V8 engine, with production lasting until 1961. A Canadian version of the Windsor was built until 1966, but it was largely a rebadged <a href="https://www.classic.com/m/chrysler/newport/">Chrysler Newport</a>.

The seventh and final generation of Chrysler Windsor was introduced for the 1959 model year. This final generation of Windsor was offered…

Windsor - 7th Gen

7th Gen

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The fifth generation of <a href="MKT:6934" old-href="https://www.classic.com/m/chrysler/windsor/">Chrysler Windsor</a> was introduced for the 1955 model year. The fifth generation Windsor remained Chrysler&#39;s entry level model, and like all Chrysler&#39;s at the time, featured a dramatic redesign by Virgil Exner. This latest generation of Windsor was offered as a coupe, sedan, or convertible, and was fitted with Chrysler&#39;s 5.0L &#39;Spitfire&#39; V8 engine. Production of the fifth generation Windsor continued until 1956, when the <a href="MKT:6940" old-href="https://www.classic.com/m/chrysler/windsor/6th-gen/">Sixth Generation Chrysler Windsor</a> was unveiled.

Vehicle	Price	Date
1955 Chrysler Windsor Newport Deluxe Mecum Louisville (2019) Lot #S153	$19,800 SOLD	Sep 21, 2019 2 years ago
1955 Chrysler Windsor Deluxe Sedan RM Sotheby's Auburn Spring (2018) Lot #5030	$15,950 SOLD	May 12, 2018 3 years ago
1956 Chrysler Windsor Newport GAA Early March (2018) Lot #FR0255	$43,000 SOLD	Mar 02, 2018 3 years ago
1956 Chrysler Windsor Convertible Mecum Los Angeles (2017) Lot #S129.1	$77,000 SOLD	Feb 18, 2017 4 years ago
1955 Chrysler Windsor Convertible Mecum Portland (2016) Lot #F30	$24,500 SOLD	Jun 17, 2016 5 years ago
1956 Chrysler Windsor Mecum Portland (2016) Lot #F99	$24,000 SOLD	Jun 17, 2016 5 years ago

Chrysler Windsor - 5th Gen (1955 to 1956)

Model years for Chrysler Windsor - 5th Gen (1955 to 1956)

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