2 Owner Mopar: 1955 Chrysler Windsor Deluxe

How great is it to find a vintage car that has only had two owners? Sometimes a low owner car can look like a train wreck, but in the case of this 1955 Chrysler Windsor Deluxe, it almost looks new. The seller has taken great care of this one since he purchased it in the early 90’s, and the seller even claims to have the original title from 1955! Although a real stunner in looks, this Windsor needs some fine tuning to be road worthy once more. This two owner beauty is offered for $12,500. Find it here on craigslist out of Gloucester, Virginia.

Although not road worthy just yet, this 301 cubic inch Spitfire V8 with its two speed automatic transmission do operate, but are in need of some fine tuning. The seller has installed many newer tune up parts and the seller suspects the point gap, and float level may be off. With very little rust present, the engine bay appears original. The owner claims this Chrysler has only covered 65,000 miles in its lifetime, which is certainly possible. The condition of this car overall certainly reflects that it has been well maintained. Perhaps with only time and patience, this one would be road ready.

Although the word “original” is thrown around in the for sale listing, the interior is not original, but is reupholstered in factory fashion. Despite using non-original fabrics, the interior is clean, and tidy, adding to the cars appearance versus an aged and damaged interior. The steering wheel is faded, and cracked, but thankfully the dash made out much better in its trip through time. A custom carpet kit was added, and the headliner was replaced as well. All of the interior aspects match nicely. I applaud the seller for the nicely done interior, despite it not being original.

Looking over the exterior of this Windsor can almost fool you into thinking it has way less than 65,000 miles. The paint is wonderful, with a rich shine and excellent color. The chrome work on this car is excellent, and 99% complete. The 1% of trim missing comes from two missing “Deluxe” badges that go on the front fenders. Rust, corrosion, paint chipping, or any other defects, are not visible from the photos, making this Chrysler appear as an excellent survivor, or perhaps a moderately restored vehicle. What do you think? Is this a survivor, or has this Mopar seen more work than just the interior restoration?


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  1. Howard A Member

    Nobody,,,in 2 hours, for shame. What a striking automobile. Who cares whether it’s original or not, try and find another. If you want to cruise in one of the finest cars of the mid-50’s, here it is, but it’ll cost ya, but comparatively speaking, in 1955, it cost someone a heck of a lot more. This car sold for, what, $3800 maybe (?) new in ’55, that’s like $34,400 bucks in today’s money. If you didn’t go the Caddy, Imperial, Lincoln ( Packard?) route in ’55, this was the next step down. The hemi is a slug and for pure nostalgia, I suppose it could remain, but a modern motor puts out more hp and gets way better mileage.( but you lose the hemi “charm”) Out of my league, but a fantastic car nonetheless.

    • Don

      It’s a poly not a hemi .wiki

      • Howard A Member

        Oops, thanks Don.

      • John H. from CT

        in ’55 the top motor was the 331 Hemi. in the New Yorker Deluxe St. Regis with a 4 BBL and in the ’55 Chrysler 300 it was the 331 with twin 4 BBLs. You could get 20 MPG on the highway with these. I know because the NYDSR was my family car and the first car I learned to drive on. I still miss ours….

        Like 1
      • CR Parish

        1957 was the first year for the poly.

  2. JW454
  3. Adam T45 Staff

    Cool looking car. Like it a lot.

  4. Coventrycat

    Good looking, honest car. If factory style interior upholstry can be found, great, if not, fine as is. Love those taillights.

  5. Paul B

    I always felt these were more interesting and had more presence than a Buick, Oldsmobile, Nash or Mercury. Packards were somehow up a notch and very classy, and by this time Hudsons were warmed-over Nashes. Not my kind of car but very impressive nevertheless and deserving of a new life.

  6. Bruce Fischer

    Mines got 85,000 original miles on it but needs paint. All the gadges and all in side lights still work. I have gone over the brakes and new tires, just waiting for a master cylinder to come in for it before I start getting her ready for a nice gun metallic gray paint job and I am going to leave the pink stripe. Bruce.

    • Eric 10Cars

      Nice one, Bruce. I personally like the 56’s better than the 55’s…cleaner look to my eyes. Also they got rid of that awful dashboard shifter and went to the pushbuttons which I thought was too cool as a kid. Agree with keeping the pink stripe. Chrysler loved their 2-tones (my Dad’s 54 Windsor was medium blue with black top) and this less aggressive pink stripe would be great with a gray combo (which looks to be the color you have already sort of). Pink is such an idiosyncratic and potentially controversial color on a car that I personally prefer it used as an understated accent color, as yours does.

  7. Lorraine Schmertzing

    Any leads on where I can find parts for a 55 Chrysler Windsor Deluxe Convertible? thanks – I tried ebay.

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