Chrysler Windsor Classic Cars for Sale

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1940 Chrysler Windsor for sale 101057931
120 Photos
1940 Chrysler Windsor for sale 101057931 1940 Chrysler Windsor for sale 101057931

1940 Chrysler Windsor

$39,900

  • 2
  • 3,956 miles
1940 Chrysler Windsor Convertible The Chrysler Windsor automobile, named after the Royal House of the UK, first came out in 1939. It was a junior model to the larger Chrysler New Yorker. In 1940, t... More Info ›
Classic Auto Mall Inc
Morgantown, PA 19543 (115 miles from you)
(877) 516-3869
1955 Chrysler Windsor for sale 101212835
40 Photos
1955 Chrysler Windsor for sale 101212835 1955 Chrysler Windsor for sale 101212835

1955 Chrysler Windsor

$12,400

  • 1
  • 301 ci Poly
  • 37,045 miles
1955 Chrysler Windsor Sedan The Chrysler Building is one of the most beloved of New York Citys skyscrapers, an architectural manifestation of both the Art Deco era and the automobile age. Famous as... More Info ›
Classic Auto Mall Inc
Morgantown, PA 19543 (115 miles from you)
(877) 516-3869
1960 Chrysler Windsor for sale 101205686
4 Photos
1960 Chrysler Windsor for sale 101205686 1960 Chrysler Windsor for sale 101205686

1960 Chrysler Windsor

$17,500

  • 4
  • RED
  • 383
  • 86,000 miles
1960 Chrysler Windsor (Waynesville, OH) $17,500 obo | You are looking at a very sharp all original Windsor with only 86k actual. The red exterior was recently repainted and it came out even better ... More Info ›
Auto Market King
Pittson, PA 18640 (181 miles from you)
(833) 724-1713
1948 Chrysler Windsor for sale 101304916
5 Photos
1948 Chrysler Windsor for sale 101304916 1948 Chrysler Windsor for sale 101304916

1948 Chrysler Windsor

$21,995

  • Blue
  • 8,000 miles
1948 Chrysler Windsor 4 door with suicide rear doors and original motor and fluid drive trans runs and drives great and is a good eye Turner and also has a speaker System. Please Note The Followin... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
1953 Chrysler Windsor for sale 101039561
5 Photos
1953 Chrysler Windsor for sale 101039561 1953 Chrysler Windsor for sale 101039561

1953 Chrysler Windsor

$9,995

1953 Chrysler Windsor a rare beauty. Runs great! Can drive this anywhere! Can be an everyday driven if you wish. ZERO mechanical issues. New tires, Clean original interior, (one 2inch rip on front ... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
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1950 Chrysler Windsor for sale 100890306
21 Photos
1950 Chrysler Windsor for sale 100890306 1950 Chrysler Windsor for sale 100890306

1950 Chrysler Windsor

$15,295

1950 Chrysler Windsor 49K Original Miles Rare Barn Find. Mechanically the car is excellent with only 49,804 ORIGINAL miles. Nice easy starting, whisper quiet motor with smooth shifting transmission... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
1954 Chrysler Windsor for sale 100824173
6 Photos
1954 Chrysler Windsor for sale 100824173 1954 Chrysler Windsor for sale 100824173

1954 Chrysler Windsor

$6,695

1954 Chrysler Windsor Deluxe 2 door coupe. Original 6 in line engine and powerglide transmission, runs and drives, fuel tank needs to be cleaned, electrical fuel pump, all new brakes. Will need a b... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
1953 Chrysler Windsor for sale 101318694
24 Photos
1953 Chrysler Windsor for sale 101318694 1953 Chrysler Windsor for sale 101318694

1953 Chrysler Windsor

$11,795

  • Green
  • 265
1953 Chrysler Windsor Deluxe Completely restored reconditioned daily driver. New high quality high luster cloth upholstery with new carpet. Original headliner because it still looks new. The origin... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
1949 Chrysler Windsor for sale 101144556
12 Photos
1949 Chrysler Windsor for sale 101144556 1949 Chrysler Windsor for sale 101144556

1949 Chrysler Windsor

$9,795

1949 Chrysler Windsor. Great cruising sedan. New tires, am/fm/cd under dash. No rust, solid car. Some pitting of chrome. Super soft ride. Fluid drive transmission, you use the clutch to begin, then... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
1948 Chrysler Windsor for sale 100823500
4 Photos
1948 Chrysler Windsor for sale 100823500 1948 Chrysler Windsor for sale 100823500

1948 Chrysler Windsor

$12,495

1948 Chrysler Highlander Project !!! More Photos will be posted later. This is a rare car that needs to be restored. Does run and yard drive with a small block Chevy motor and trans. More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
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1948 Chrysler Windsor for sale 100860619
7 Photos
1948 Chrysler Windsor for sale 100860619 1948 Chrysler Windsor for sale 100860619

1948 Chrysler Windsor

$18,995

1948 Chrysler Windsor. Restored. New interior, grill has been re-chromed, radial wide white wall tires, fender skirts, 6 cylinder 3 speed manual shift, and a new fuel tank and sending unit. Lots of... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
1957 Chrysler Windsor for sale 101278460
12 Photos
1957 Chrysler Windsor for sale 101278460 1957 Chrysler Windsor for sale 101278460

1957 Chrysler Windsor

$40,995

  • Beige
1957 Chrysler Windsor Station Wagon All Original This car is absolutely a time capsule. Its like going back in 1957 and buying it then. This car is all original absolutely a gorgeous vehicle.Must ... More Info ›
Classic Car Deals
Cadillac, MI 49601 (548 miles from you)
(844) 676-0714
1946 Chrysler Windsor for sale 100881686
10 Photos
1946 Chrysler Windsor for sale 100881686 1946 Chrysler Windsor for sale 100881686

1946 Chrysler Windsor

$9,750

  • 32
  • Blue
  • 8 Cylinder
St Rod, small block Chevy V8, auto trans, nice body and paint, original interior, original chassis, runs/drives. | More Info ›
Country Classic Cars
Staunton, IL 62088 (658 miles from you)
Click for Phone ›
1950 Chrysler Windsor for sale 101244577
11 Photos
1950 Chrysler Windsor for sale 101244577 1950 Chrysler Windsor for sale 101244577

1950 Chrysler Windsor

$13,950

  • 3
  • Blue
  • 6 Cylinder
1950 Chrysler Windsor 2door sedan, well kept, solid southern body, nice paint, nice redone interior, 54,xxx actual miles, flathead, 6cyl fluid drive, www tires, nice chrome, runs and drives. | More Info ›
Country Classic Cars
Staunton, IL 62088 (658 miles from you)
Click for Phone ›
1949 Chrysler Windsor for sale 101344881
12 Photos
1949 Chrysler Windsor for sale 101344881 1949 Chrysler Windsor for sale 101344881

1949 Chrysler Windsor

$12,850

  • Blue
  • 6 Cylinder
4dr sedan, same owner for years, 64,xxx miles believed to be actual, nice quality older restoration, good body and paint, nice redone interior, flathead 6cyl fluid drive, www tires, runs and drives | More Info ›
Country Classic Cars
Staunton, IL 62088 (658 miles from you)
Click for Phone ›
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1950 Chrysler Windsor for sale 101330628
11 Photos
1950 Chrysler Windsor for sale 101330628 1950 Chrysler Windsor for sale 101330628

1950 Chrysler Windsor

$9,950

  • 4
  • Gray
  • 6 Cylinder
1950 Chrysler Windsor 4dr sedan, well kept original car, believed to be 58,xxx actual miles, good body, original paint, good redone interior, recently serviced , full tune up and trans, flathead 6 ... More Info ›
Country Classic Cars
Staunton, IL 62088 (658 miles from you)
Click for Phone ›
1956 Chrysler Windsor for sale 101090071
27 Photos
1956 Chrysler Windsor for sale 101090071 1956 Chrysler Windsor for sale 101090071

1956 Chrysler Windsor

$10,500

  • 7
  • Teal/Mint
  • 331 CID V8 Polly
  • 30,198 miles
Gateway Classic Cars is excited to present this 1956 Chrysler Windsor for sale by our Tampa Showroom. This awesome piece of history is sure to stand out with its mint green and dark green exterior ... More Info ›
Gateway Classic Cars
O Fallon, IL 62269 (669 miles from you)
Click for Phone ›
1949 Chrysler Windsor for sale 101084843
28 Photos
1949 Chrysler Windsor for sale 101084843 1949 Chrysler Windsor for sale 101084843

1949 Chrysler Windsor

$33,500

  • 3
  • Blue
  • Inline 6
  • 2,000 miles
Gateway Classic Cars of Orlando is proud to offer this 1949 Chrysler Windsor. This classic Windsor runs very well and drives just like it looks. It is powered by a Flathead inline 6-cylinder and It... More Info ›
Gateway Classic Cars
O Fallon, IL 62269 (669 miles from you)
Click for Phone ›
1951 Chrysler Windsor for sale 101343949
99 Photos
1951 Chrysler Windsor for sale 101343949 1951 Chrysler Windsor for sale 101343949

1951 Chrysler Windsor

$9,950

  • 1
  • Blue
  • I6 250.6 cid 116 hp
  • 64,300 miles
ALL VEHICLES ARE SHOWN BY APPOINTMENT ONLY, AND MAY OR MAY NOT BE LOCATED IN OUR STANLEY, WI SHOWROOM! | In 1951, the Windsor became Chryslers price leader (entry level) and retained the styling ... More Info ›
Cody's Classic Cars
Stanley, WI 54768 (801 miles from you)
(833) 540-0738
1955 Chrysler Windsor for sale 101353548
1 Photo

1955 Chrysler Windsor

For Auction

  • TWO TONE
  • 76,562 miles
1955 CHRYSLER WINDSOR More Info ›
A Better Bid Car Auctions
North Miami Beach, FL 33162 (920 miles from you)
(877) 771-6224
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1950 Chrysler Windsor for sale 101133060
51 Photos
1950 Chrysler Windsor for sale 101133060 1950 Chrysler Windsor for sale 101133060

1950 Chrysler Windsor

$12,000

  • 8
  • Green
  • 6 Cylinder
  • 105,000 miles
Very well maintained 1950 Chrysler Windsor 4-door sedan. This is the second owner 19 years. The car is rust-free, all original with Factory color green and has a new interior. Windsor was garaged. ... More Info ›
Old Iron AZ LLC
Tuscon, AZ 85743 (1937 miles from you)
(844) 320-0378
1955 Chrysler Windsor for sale 101322698
32 Photos
1955 Chrysler Windsor for sale 101322698 1955 Chrysler Windsor for sale 101322698

1955 Chrysler Windsor

$11,850

  • 1
  • 8-cyl. 301cid/188hp 2bbl
  • 76,562 miles
THIS 1955 CHRYSLER WINDSOR IS LOCATED IN: VAN NUYS, CA The Chrysler Windsor is a full-size car which was built by Chrysler from 1939 through to the 1960s. The final Chrysler Windsor sold in the Uni... More Info ›
Vintage Car Collector
Glendale, CA 91203 (2268 miles from you)
(833) 295-3354
1948 Chrysler Windsor for sale 101287335
45 Photos
1948 Chrysler Windsor for sale 101287335 1948 Chrysler Windsor for sale 101287335

1948 Chrysler Windsor

$18,500

  • 1
  • Beige
  • 6 Cylinder
  • 95,000 miles
ORIGINAL-ORIGINAL-ORIGINAL rare Highlander interior package. Purrs like a kitten.  New period correct brakes ($4000), semi-automatic, nicely operating trans, properly tuned. No rust, stored insid... More Info ›
Portland, OR 97232 (2320 miles from you)
Click for Phone ›
Private Seller
Enhanced Listings
1949 Chrysler Windsor for sale 100996005
10 Photos

1949 Chrysler Windsor

$19,900

  • 3
  • Yellow
Goldenrod Garage
Freeport, ME 04032 (506 miles from you)
(866) 678-0179
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