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Windsor

5th Gen

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Chrysler Windsor - 5th Gen (1955 to 1956)

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

The fifth generation of Chrysler Windsor was introduced for the 1955 model year. The fifth generation Windsor remained Chrysler's entry level model, and like all Chrysler'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's 5.0L 'Spitfire' V8 engine. Production of the fifth generation Windsor continued until 1956, when the Sixth Generation Chrysler Windsor was unveiled.

Chrysler Windsor - 5th Gen FAQs

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

1955
1956

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Showing 15 of 39 related listings

Dearborn, MI, USA

1955 Chrysler Windsor Deluxe Newport

Original & Highly Original

57k mi

Automatic

LHD

Not Sold

$14,750

Hemmings

Mar 7, 2023

Details

SAVE

Lot 8588: 1955 Chrysler Windsor Deluxe Newport

Not Sold

$14,750

57,000 mi
Location: Dearborn, MI, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

West Columbia, SC, USA

1956 Chrysler Windsor

Original & Highly Original

18k mi

Automatic

LHD

Sold

$9,525

Hemmings

Jan 20, 2023

Details

SAVE

Lot 8149: 1956 Chrysler Windsor

Sold

$9,525

18,247 mi
Location: West Columbia, SC, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

West Columbia, SC, USA

1956 Chrysler Windsor

Original & Highly Original

18k mi

Automatic

LHD

Not Sold

Hemmings

Dec 17, 2022

Details

SAVE

Lot 5511-PC: 1956 Chrysler Windsor

Not Sold

18,247 mi
Location: West Columbia, SC, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Chicago, IL, USA

1956 Chrysler Windsor Newport

Original & Highly Original

76k mi

Automatic

LHD

Sold

$17,050

Mecum

Oct 13, 2022

Details

SAVE

Lot T48: 1956 Chrysler Windsor Newport

Sold

$17,050

76,218 mi
Location: Chicago, IL, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Fayetteville, NC, USA

1956 Chrysler Windsor Sedan

Original & Highly Original

66k mi TMU

Automatic

LHD

Sold

$20,500

Bring a Trailer

Oct 3, 2022

Details

SAVE

Lot 86236: 1956 Chrysler Windsor Sedan

Sold

$20,500

66,000 mi TMU
Location: Fayetteville, NC, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

West Columbia, SC, USA

1956 Chrysler Windsor

Original & Highly Original

18k mi

Automatic

LHD

Not Sold

$12,000

Hemmings

Aug 12, 2022

Details

SAVE

Lot 5511: 1956 Chrysler Windsor

Not Sold

$12,000

18,247 mi
Location: West Columbia, SC, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Harrisburg, PA, USA

1955 Chrysler Windsor

Original & Highly Original

4k mi TMU

Automatic

LHD

Sold

$16,500

Mecum

Jul 28, 2022

Details

SAVE

Lot T112: 1955 Chrysler Windsor

Sold

$16,500

4,612 mi TMU
Location: Harrisburg, PA, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

Kissimmee, FL, USA

1956 Chrysler Windsor Newport

Modified

76k mi

Automatic

LHD

Sold

$11,000

Mecum

Jan 16, 2022

Details

SAVE

Lot U16: 1956 Chrysler Windsor Newport

Sold

$11,000

76,218 mi
Location: Kissimmee, FL, USA
Originality:
Modified

Vehicles with a period-correct engine and body, with multiple significant modifications such as change in color, increased displacement, added performance equipment (Turbo, Supercharger), spoilers or bumpers, etc. Generally, removable modifications.
Transmission: Automatic
Driver side: LHD

Vehicle Details

WEBSITE

1955 Chrysler Windsor 4 Door Deluxe Sedan

Torrance, CA, USA

1955 Chrysler Windsor 4 Door Deluxe Sedan

Original & Highly Original

64k mi

Automatic

LHD

Price Undisclosed

West Coast Classics

Jun 25, 2019

Details

SAVE

Lot 927: 1955 Chrysler Windsor 4 Door Deluxe Sedan

Price Undisclosed

63,950 mi
Location: Torrance, CA, USA
Originality:
Original & Highly Original

Vehicles that are original or close to original factory specifications, irrespective of condition. May include vehicles that have minor, removable modifications such as aftermarket wheels, exhaust, or accessories such as cargo/roof rack, stereos, etc.
Transmission: Automatic
Driver side: LHD