Two Door Survivor: 1959 Chrysler Windsor

Packing loads of style, a beautiful survivor appearance, and some neat features, this 1959 Windsor is hard to ignore. Simple with its white and red paint, this surviving example has covered only 83,000 miles in its lifetime while always being pampered with a garage to sleep in. Needing little to nothing, this great looking Mopar is offered for $20,000. Take a look at it here on craigslist out of San Francisco, California.

Beneath the hood lies a low mileage Golden Lion 383 V8 mated to an automatic transmission. With a good detailing job this bay would “pop” and offer a very nice view. The seller has owned this car for 14 years and is the second owner of this beauty, making the mileage seem more valid. I would assume the drive-train to be in good health with no major issues or concerns.

Optioned with the legendary swivel seats, this Mopar is easy on the knees and back getting in and out of. Also this Mopar has the optional mirrormatic mirror, and a large back window.

The cockpit offers an awesome view of this miraculously clean and tidy dash layout. Appearing flaw free, the dash is a beautiful work of craftsmanship with all of its fine details. The only major gripe from the interior is that the driver seat has a few split seat seams, but otherwise this one is clean and in very nice survivor shape.

Being a two door earns this Mopar some points, among many other great features and styling cues. The large back window offers a wealth of sight, and the fins and taillights are just enough to make you say “Oh Yea.” The paint and body work appear very nice, and after spending some time studying this fine machine there is little in the way of visible exterior flaws. The only real flaw I could manage to find is a very small ding on the rear bumper on the passenger side. Otherwise there is no visible rust, rot, or dents. Absolutely stunning, are you a fan of this 59 Windsor?

Fast Finds


  1. Gunner

    Wow. Nice reference Brian on the “cockpit”. This model really stands out for the late 50’s Chrysler products. They had the “bubbletop” before bubbletop. So cool in every way…..and those swivel seats! 59 was indeed a great year for Detroit. The problem with us gearheads? We want sooooooooo many beautiful automobiles! How do we choose?

  2. 68 custom

    beautiful Mopar and the swivel buckets and the 383/torque flight would make this one for me if I had the cash in my sock drawer. sadly I do not so I hope the next owner cherishes this sweet ride!

  3. jdjonesdr

    I had a 72 Monte Carlo with Swivel seats. I always thought they were the coolest things ever.

    • Graham

      Didn’t think the ’72 Monte came with swivel buckets. I know my 72 didn’t and the first ones I saw working at a Chev dealership were in ’73

  4. Howard A Member

    Friend’s dad across the alley had a ’59 Chrysler. May have been a 4 door, but I remember those tail lights. It stuck out of their garage by a foot. I believe that alternator was added. The 1960 Valiant was the 1st Mopar with an alternator. My dad’s partner had a DeSoto with those seats. Just a tank by today’s standards. Great find.

  5. Will

    Price seems a bit steep but I do love that swivel out seat. Here’s the saved ad with all the images


    what a car!

  7. Dave

    Looks like the Dodge version in the background. Dude has both of them?

    • Imperialist1960

      If that’s who I think it is, dude has 10 that he rotates around a neighborhood with the most vicious meter maids west of the Lower East Side. He was up to it in the early 1990’s when I lived in that neighborhood.

      If you buy the car and the seller is a ringer for Kramer, you are dealing with one dedicated Fin Fanatic.

  8. Rustytech Member

    This would have been manufactured with a generator, so yes the alternator is an upgrade. Beautiful car, and being a Mopar guy I would love to have it, $20k doesn’t sound high to me, but too high for me!

  9. Sam Sharp

    The 1959 tv ad salesman quoted about the seats; “the doors swing wide to greet ya’, and the seat swings out to seat ya.’ ” Can’t remember the exact verbage.

    As a Chrysler engineer’s kid I was able to see a clay mock-up that was to be this model, and others. Still don’t know how I was privileged to get to see the clays.

    The big Chryslers of the day did well at the drags. I saw a 59 Chrysler coupe beat a 59 Impala. Soundly. If this car was a chebby it would be listed at $48,000.

    • Kevin W

      I’ll take the Chrysler. 59 shevrolays are ugly enough to stop an eight day clock. Lol.

  10. Kiwi Cortina

    This car and others from the same stable all 59-60 era come up for sale every year on Craigslist and a friend of mine has tried to buy them several times but the seller seems to be on a fishing expedition just to see how many people are interested. As you can see in one of the pictures another finned beauty lurking in the background which as I mentioned my friend has tried to purchase. Good luck to potential buyers, hope they have more luck than we have had in the past 6 years trying to buy one from this collection.

  11. Ed P

    This car has a 383 rb engine that was only made for 59-60 Chrysler cars. Oddly, the 383 b engine was used in Desoto & Dodge from 59 on and Plymouth starting in 60.

  12. RicK

    I take exception to the author’s characterization of the dash as flawless (or whatever). From the photo, what appears to be the original black vinyl dash cover on the passenger side, especially next to the radio speaker grill looks totally warped and whooped out unless I’m not seeing it right in the photo. Otherwise I like the Dodge way better, and would like it even more if it was in as nice condition as the Chrysler.

  13. Kevin

    That’s a delco alternator. There’s always gotta be a government motors component in the mix to spoil it.

  14. leiniedude leiniedude Member

    I saw a convertible of this year last week at a show in New Glarus Wisconsin with the swivel seats. I never knew. Pretty good idea, with the fifty way power seats of today I am surprised it is not offered these days. Can someone tell me what the mirrormatic mirror does? Thanks, Mike.

    • Kevin W

      I believe it is an automatic day/night mirror.

  15. Johnrm

    I have seen this and others from the collection off and on for years. No idea how many he has but it is indeed a full time job rotating them around and not getting tickets in SF.

    • Kevin W

      You mean these cars are parked on the street all day? Night time too? Seriously? Is this guy nuts or something?

  16. Sam Sharp

    Uh oh. The ref to the eight day clock gives away the background of Kevin. The cockpits of ‘nex-gen’ aircraft bear no semblance to the ‘pit on the Chizzler.

    The Ponchos of the day were the scourge of many chubby chebby drivers in stock production class. I hate being poor… the Chizzler and Poncho would be in my shop.

  17. Nick

    I own this car. Barnfinds: Nice embellishment of my ad from Craigslist. Maybe it will help sell it. Kiwi Cortina: make a good offer and I’ll sell. Yes, I am fickle with my cars, because once they’re gone they’re hard to find again.

    • Stanley

      Hey nick,

      I sold you this family 59 Windsor. Just happened upon this and knew it was certainly the same car. Do you still have it?

      • Nick Nichols

        Yes, still have it! I almost sold it but I got cold feet. Decided to keep it.


  18. Michael

    Nick- hey it’s michael, you sold me that 56 Studebaker long ago- still running strong!

    • Nick Nichols

      Great to hear! Where are you living now? Nick

      • Michael

        Lodi- I’m at will send you photos. Hope you are well! m

  19. Fred

    Wow, My first car was a ’59 Windsor like this, except mine was lavender with a white top and grey interior. Mine was a one-owner, having been bought new by my dad’s aunt and was in excellent condition. Dad bought it at her estate sale in 1970 for $150, it had 38,000 miles and became my first car two years later. That Golden Lion 383 would smoke the tires from here to there LOL.

  20. Miguel

    What bothered me most about these big Chryslers was that there was no park.

    You had to use the emergency brake to keep the car still when parked.

    The most expensive cars from Chrysler in the early ’60s didn’t have park but the Valiant’s did.

    It was a very weird world back then.

    • Kevin W

      Try throwing a vehicle into park while it’s rolling sometime. Although it will make a ratcheting sound as the parking pawl jumps, it will keep rolling. Push button Chrysler’s had a transmission mounted park brake, the same as heavy duty pickups years ago. Probably more reliable than a park gear.

      • Ed P

        Some folks have complained that the parking brake would not hold. I wonder if they ever adjusted or repaired the unit. I have driven many trucks with this setup and they worked fine.

    • Ed P

      It depended on the automatic transmission. The early Torqflite A488, used from 56-61 did not have a parking paw. The Valiant used the, new for ’60, A904 6 cyl transmission. The A727 came out for 62 and had a paw.

      • Kevin W

        I had a 62 Chrysler 300H, still kicking my ass for selling it, and it had no park gear, parking brake only

      • Ed P

        The parking pawl must have become available on 63 m.y. cars built in ’62

  21. Fred

    Yep, it was a band-brake on the transmission output shaft operated by a pull-type actuator under the right side of the steering column. I clearly remember using it for a panic stop one time!

  22. donald jones

    Istill would rather have this car than the lowest priced new car the nissan versa 13759 and besides upside potential , you never know what a good offer may do .

  23. Hide Behind

    Heard no bad, no spoken bad, an see no bad.
    Three monkeys all agree.
    Worthy auto for buy and drive, at $20-22k.
    Just out of my reach, and should go farther yet.
    Nice comfortable gas guzzling auto for a weekend leisurely drive to the beach.

  24. howard maryles

    Hmmm,too bad it’s a 2 door!

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