Drive It Anywhere: 1953 Chrysler Windsor

Drive it anywhere isn’t a term used all that often when describing a classic car, but it does pop up from time to time. Shiny and clean, this ’53 Windsor looks like a great surviving classic that is in tip top health. Having only a few apparent flaws, this driving classic is offered for a reasonable $5,950. Take a look at it here on craigslist out of Chewelah, Washington.

Beneath the hood is a rather tidy engine bay and a 264 cubic inch flathead inline 6. The only thing I can say I am not in love with, is the fact that this Chrysler is propelled via a Fluid-Drive semi-automatic transmission, but I can’t complain as this car is a flawless driver.

Ignoring the snow leopard seat covers, this interior shows very nicely. The flooring is dirty, but would clean up easily enough. The dash is stunning as is the steering wheel. Appearing quite original, this interior only has a few minor flaws to show. The seats are likely ripped which is why there are covers installed, and secondly the door panels could use a little work, but as a whole are in very reasonable shape.

Sleek and shiny, the exterior is beautiful with no easily apparent flaws to the exterior. The image quality is low, but this looks like a great survivor, or possibly repainted driver. All of the trim is in its place, and all of it is quite shiny as well. The glass is intact, and even the hubcaps are still hanging around after 64 years. With great looks inside and out, and the ability to “drive it anywhere” sure makes this Windsor seem like a great opportunity for a classic driver. Would you jump on this clean affordable cruiser?

Fast Finds


  1. David montanbeau

    The 264 is a highly desired engine for hot roding. Nice care.

  2. Howard A Member

    Seeing these cars brings back such fond memories of youth. In the late 60’s, a guy down the block, George, who was older and had his license, bought a car very similar to this, only a ’54 and yellow. Same 6 only with “Powerflite” trans ( 1st year fully automatic) in perfect shape with a thrown rod from the original owners. I remember, it was spotless. I think they even had a name for it. When he bought it, he had to promise the people he would fix it and take care of “Gretchen” ( or whatever) Sure he would, he said. He fixed it alright. He got a 276 (?) Hemi from a junked ’54 DeSoto, we dropped it in ( one of the 1st motor swaps I can remember) and he literally trashed that car ( did some great burnouts until the trans puked) Goodbye Gretchen. I always felt sorry for those people, if they ever saw what George did to poor Gretchen.
    Love these dashboards. Cool car, and while you’ll win no stoplight drags with this, you might get halfway decent mileage.

    • Dave Wright

      The first car I have conscious memory of that my folks owned. I am sure my little brother came home from the hospital in it. These were really good cars.

      • Eric_10cars

        My dad bought a 1954 Windsor in December of 1953…same Spitfire 6 and fully automatic transmission. 2-tone paint job (black top, medium light blue for the rest), padded dash, fancy radio, power steering. $3000 at Heckman Motors in Croton-on-Hudson. He had several major collisions driving back and forth from Ossining to lower westside Manhattan (below Canal Street) every day. He had it repaired each time. Had to have the transmission rebuilt and it never had the same pop in low range that it did originally. He finally started taking the NY Central train in every day and it became a station car for a few years. He then took it into the city and parked it in a garage close by his machine shop to use around the city as he needed it. By that time it had about 225K on it…a lot for northern commuter vehicle in those days. It finally ended its life when a drunken garage attendant managed to ram all 4 quadrants into the concrete piers of the garage. Big, plush, luxurious and took the family on many trips around the east coast. Several of his friends bought similar vehicles at the same time, some Windsors, some New Yorkers (with the hemi v8). Always wished ours had been a New Yorker, but c’est la vie.

  3. Chris

    I’d trade my 53 chevrolet for it in a heartbeat!!!

    • glen

      Yours looks really good, Ontario Historical plate?

  4. jw454

    I have a very fuzzy memory of one of these being used in a “Baha” type race in Mexico some years back. As I recall, it did quite well.

  5. Dngfld

    When I was 6 or 7 my father bought a similar ’53, but 2 door in maroon….what nice car, but mother was not thrilled as there were 5 kids! It was a great car and I would love to find that car.

  6. Mountainwoodie

    What a great platform and entry into the world of preserving old cars!. Get up and go! While it is stately looking and Howard has a point with it running in the Panamerican races back in the day, I always thought them somewhat dowdy looking in comparison to a ’53 or ’54 Chevrolet. That said, for years there was a commercial limousine variety of the this car sitting on a street in San Diego. No division window but stretched.

  7. Mountainwoodie

    This guy has 18 cars for sale! (if I can add). I’d like to see the Mercury with the breezeway.

  8. Dan

    Maybe the perfect car for my planned trip down Route 66.


    Suicide door conversion…lowered…bagged…all disc brakes…wider vintage look tires/wheels…buffalo hide leather seats…modern infotainment & climate control behind vintage dash…keep the original paint / patina…HEMI.

  10. RNR

    My dad traded the ’52 Plymouth Belvedere he bought new (my first ride home from the hospital) on a used dark blue ’53 Windsor 4 door because he wanted to trade up to a Chrysler. I was playing “car salesman” one day and burned my finger on the cigar lighter. I remember cleaning out the glove box the day Dad traded the Windsor in for a new ’60 Valiant. Any wonder I still drive MoPars?

  11. Timothy Neal

    Nice. I have a 55 Chrysler windsor deluxe needs work on ex and interior but does run.

  12. dr fine

    I love the 1953 tip-toe semi automatic. It’s essentially a four speed manual with electric shift between 1-2 and 3-4. ’53 was the last year for it, and it finally got a torque convertor. My dad traded our ’50 Windsor (6) for a ’53 hemi because the ’50 was such a slug. I wound out the hemi thru all four gears and had a great time. I was very surprised when my friend’s dad drove us downtown in his ’53 Windsor six with the same trans. It had plenty of get up and go. It was the torque convertor more than the six that affected performance.

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