Used Chrysler Windsor Convertible For Sale (23 results)

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Model:Windsor

Body:Convertible

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highlander convertible fluid drive low mile ca car
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1955 chrysler windsor convertible barn find

Discover this stunning 1955 Chrysler Windsor Deluxe Convertible, a rare barn-find featuring original red exterior and interior. This classic needs total restoration, showcasing its vintage charm and factory wire wheels

1 mi.

Red

Convertible

automatic

$1,500,000

1949 chrysler windsor convertible -- restored 77,000 mile west coast car

Discover the beautifully restored 1949 Chrysler Windsor Convertible with just 77,000 miles. This classic car features a power soft top, inline six-cylinder engine, and a stylish blue exterior that turns heads wherever it goes

77,343 mi.

Blue

Convertible

manual

1949 chrysler windsor highlander with fluid drive - low mile california car

This stunning 1949 Chrysler Windsor Highlander Convertible boasts only 82,000 miles and comes as a fully equipped classic car with a power convertible top and a smooth Fluid Drive transmission, making it a rare gem for collectors

82,640 mi.

Yellow

Convertible

gasoline

$1,850,000

1955 chrysler windsor convertible barn find, no reserve

This 1955 Chrysler Windsor Deluxe is a barn find with a striking Navajo Red exterior. Although it requires a total restoration, it features original paint and interior, and comes with factory wire wheels. A rare opportunity for classic car enthusiasts

1 mi.

Red

Convertible

automatic

1963 chrysler windsor rare classic convertible

Dive into classic luxury with this 1963 Chrysler Windsor Convertible, a Canadian-only model. This unique vehicle combines rich history with elegant design, featuring a sophisticated green exterior and a stylish black interior

91,750 mi.

Green

Convertible

automatic

1950 chrysler windsor convertible street rod

Experience the beauty of this stunning 1950 Chrysler Windsor Convertible, featuring a Viper Red exterior and a beige interior. With only 3,051 miles since a complete frame-off restoration, this classic is a true head turner with all the power you need

3,051 mi.

Red

Convertible

automatic

gasoline

1951 chrysler windsor deluxe/plus convertable

Introducing a 1951 Chrysler Windsor Deluxe/Plus Convertible. This solid Coupe comes with new cloth interior, while the convertible is being sold for parts. Both vehicles have titles, making it a great project for restoration enthusiasts

Convertible

for sale: 1955 chrysler windsor in parkers prairie, minnesota for sale in parkers prairie, mn

For sale is a 1955 Chrysler Windsor convertible. It requires restoration with a rusted frame and missing parts, but includes original side windows and components for a conversion

Convertible

Parkers Prairie, MN

$1,501

rod & custom magazine car 1957 barris bailon kustom

This unique 1950 Chrysler Windsor convertible, customized in the 1950s, features classic touches like Cadillac bumpers and Lincoln taillights. It runs freely with some rust needing repair, and it's an originally Californian car with a fascinating custom history

24,529 mi.

Red

Convertible

automatic

gasoline

1949 chrysler windsor convertible no reserve

Presenting a 1949 Chrysler Windsor convertible that’s seeking a new owner. While it has significant mileage, this classic beauty boasts minimal rust and is a restoration project waiting to happen

9,999,999 mi.

Blue

Convertible

gasoline

1955 chrysler windsor convertible & 1956 chrysler new yorker sedan

Discover a rare 1955 Chrysler Windsor Convertible, a straight car requiring restoration with classic lines. It features factory red paint, original door panels, and includes factory wire wheels with white wall tires. A true barn find with great potential!

Red

Convertible

$1,350,000

1949 chrysler windsor convertible, 350ci v8, power top / vintage air / custom!

Experience a one-of-a-kind 1949 Chrysler Windsor Convertible featuring a modern powertrain, stylish leather interior, and ICE COLD AIR, perfect for cruising in style!

3,670 mi.

Red

Convertible

automatic

gasoline

$4,500,000

convertible original classic florida car

This beautiful 1950 Chrysler Windsor Convertible features a light yellow exterior and green leather interior, powered by a robust 250 CID engine with 116 horsepower, and comes equipped with a Prestomatic fluid drive semi-automatic transmission

61,510 mi.

Yellow

Convertible

automatic

1955 chrysler windsor convertible barn find, rebuilt engine and transmission

This stunning 1955 Chrysler Windsor Convertible in Navajo Red is a rare barn find. With original paint, interior, and optional wire wheels, it only needs minor restoration to be road-ready

1 mi.

Red

Convertible

automatic

$1,690,000

1940 chrysler windsor convertible~resto 350 v8/ 700r automatic~power top

This stunning 1940 Chrysler Windsor Convertible boasts a body-off restoration and a powerful 350 V8 engine with only 20k miles. Enjoy features including power steering, AC, and a power top, all while driving a true classic

22,030 mi.

White

Convertible

automatic

1959 chrysler windsor convertible

This 1959 Chrysler Windsor convertible is one of only 961 built and features a rust-free body with new rear floor and trunk sheet metal. It has a clear title and a well-maintained mechanical system

90,000 mi.

Blue

Convertible

automatic

1950 chrysler windsor highlander convertible

Experience classic elegance with this stunning 1950 Chrysler Windsor Highlander Convertible, featuring a striking Pepper Red exterior, luxurious red leather interior, and iconic chrome details, all powered by a reliable inline-six engine

39,000 mi.

Red

Convertible

automatic

gasoline

$31,000

1963 chrysler windsor convertible - ultra rare classic convertible

This stunning 1963 Chrysler Windsor Convertible is one of just 289 ever produced, featuring a rare hunter green metallic exterior. A cherished family car, it’s well-maintained and ready for cruising

91,750 mi.

Green

Convertible

automatic

1947 chrysler windsor convertible lead sled cruiser hot rod low reserve

This 1947 Chrysler Windsor Custom Convertible Sedan is a stunning lead sled with a unique design. It features a Carson style removable hard top, custom modifications like a chopped windshield, and a fully freshened driveline for pure enjoyment

6,547 mi.

Blue

Convertible

manual

1949 chrysler windsor convertible

This 1949 Chrysler Windsor convertible is a classic that, despite its extensive mileage, is mostly all there and holds the potential for restoration. Rust is minimal, making it a great project car

9,999,999 mi.

Blue

Convertible

gasoline

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