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Chrysler

Windsor

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Chrysler

Windsor

1st Gen

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Chrysler Windsor - 1st Gen (1939 to 1942)

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

The Chrysler Windsor 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 Second Generation Windsor.

Chrysler Windsor - 1st Gen FAQs

Model years for Chrysler Windsor - 1st Gen (1939 to 1942)

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Showing 24 of 30 related listings

Indianapolis, IN, USA

1941 Chrysler Windsor

Original & Highly Original

25k mi

Manual

LHD

Last Asking

$22,000

Gateway Classic Cars

Details

SAVE

Lot NDY1886: 1941 Chrysler Windsor

Last Asking

$22,000

25,333 mi
Location: Indianapolis, IN, 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: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

Greensboro, North Carolina, USA

1941 Chrysler Windsor

Original & Highly Original

25k mi

Manual

LHD

Sold

$6,500

GAA

Jul 24, 2025

Details

SAVE

Lot TH0179: 1941 Chrysler Windsor

Sold

$6,500

25,334 mi
Location: Greensboro, North Carolina, 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: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Netherlands

1940 Chrysler Windsor Sedan

Project

80k mi TMU

Manual

LHD

Not Sold

Catawiki

Nov 11, 2023

Details

SAVE

Lot 76380745: 1940 Chrysler Windsor Sedan

Not Sold

79,999 mi TMU
Location: Netherlands
Originality:
Project

Vehicles that are partially operable or non-operable that are suitable for restoration or customization.
Transmission: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Port Huron, MI, USA

1939 Chrysler Windsor Deluxe

Original & Highly Original

64k mi TMU

Manual

LHD

Sold

$16,100

Clasiq Auctions

Oct 26, 2023

Details

SAVE

Lot 2084: 1939 Chrysler Windsor Deluxe

Sold

$16,100

64,275 mi TMU
Location: Port Huron, 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: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Auburn, IN, USA

1941 Chrysler Windsor Coupe

Original & Highly Original

TMU

Manual

LHD

Sold

$15,120

Worldwide Auctioneers

Sep 2, 2023

Details

SAVE

Lot 133: 1941 Chrysler Windsor Coupe

Sold

$15,120

TMU
Location: Auburn, IN, 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: Manual
Driver side: LHD

Vehicle Details

WEBSITE

1941 Chrysler Windsor Highlander Convertible

Santa Barbara, CA, USA

1941 Chrysler Windsor Highlander Convertible

Original & Highly Original

87k mi TMU

Automatic

LHD

Not Sold

$20,018

Bring a Trailer

Oct 12, 2022

Details

SAVE

Lot 87136: 1941 Chrysler Windsor Highlander Convertible

Not Sold

$20,018

87,000 mi TMU
Location: Santa Barbara, 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

Vehicle Details

WEBSITE

Washington, USA

1941 Chrysler Windsor Convertible

Original & Highly Original

77k mi TMU

Automatic

LHD

Not Sold

$38,500

Hemmings

Sep 3, 2022

Details

SAVE

Lot 6437-PC: 1941 Chrysler Windsor Convertible

Not Sold

$38,500

77,708 mi TMU
Location: Washington, 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

Marysville, WA, USA

1941 Chrysler Windsor Highlander Convertible

Original & Highly Original

78k mi TMU

Automatic

LHD

Not Sold

$13,200

Bring a Trailer

Aug 3, 2022

Details

SAVE

Lot 80462: 1941 Chrysler Windsor Highlander Convertible

Not Sold

$13,200

78,000 mi TMU
Location: Marysville, WA, 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

La Vergne, TN, USA

1941 Chrysler Windsor Sedan

Original & Highly Original

24k mi TMU

Manual

LHD

Last Asking

$20,000

Gateway Classic Cars

Apr 6, 2022

Details

SAVE

Lot NSH1367: 1941 Chrysler Windsor Sedan

Last Asking

$20,000

24,146 mi TMU
Location: La Vergne, TN, 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: Manual
Driver side: LHD

Vehicle Details

DEALER'S WEBSITE

El Cajon, CA, USA

1940 Chrysler Windsor

Original & Highly Original

79k mi TMU

Manual

LHD

Not Sold

$11,000

AutoHunter

Dec 6, 2021

Details

SAVE

Lot 14992334: 1940 Chrysler Windsor

Not Sold

$11,000

79,507 mi TMU
Location: El Cajon, 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: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Orlando, FL, USA

1941 Chrysler Windsor Highlander

Original & Highly Original

49k mi

Manual

LHD

Sold

$35,200

Mecum

Jul 30, 2021

Details

SAVE

Lot F138: 1941 Chrysler Windsor Highlander

Sold

$35,200

49,000 mi
Location: Orlando, FL, 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: Manual
Driver side: LHD

Vehicle Details

WEBSITE

Indianapolis, IN, USA

1940 Chrysler Custom Coupe

Custom

TMU

Automatic

LHD

Sold

$27,500

Mecum

May 19, 2021

Details

SAVE

Lot W107: 1940 Chrysler Custom Coupe

Sold

$27,500

TMU
Location: Indianapolis, IN, USA
Originality:
Custom

Highly modified and/or restored vehicles with uprated engine swaps, and/or body conversions. Generally, Restomod and Custom vehicles cannot be easily returned to their original factory specifications.
Transmission: Automatic
Driver side: LHD