Hemi Convertible: 1955 Chrysler Windsor

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After many years of storage this not so common Chrysler Windsor Convertible is a nice large convertible that needs help. Featuring great style, loads of seating, and a Hemi V8 engine, this Chrysler is a cool example of an American Convertible.  Unrestored, but in need of restoration, this Windsor can be yours for $15,000. Take a look at it here on craigslist out of Lombard, Illinois. Thank you Roger for this uncommon drop top find!

The Hemi heart is still in place, but is not a runner. Quite complete and not looking too shabby, the engine may still hold some compression.

Inside you will find the interior to be very complete and in reasonable condition for its age. Although with the interior photos you start to see some of the drawbacks of this Chrysler. The floors are very crispy with rot along the front edge of the floors, and rot in the rear floors.

You can’t deny that this Chrysler has a neat style that is quite different from a Cadillac, or other 50’s era convertibles. This convertible it stylish and plenty large enough to comfortably fit any and every one you could need in one convertible. Although this looks like a nearly ready to drive survivor, my guess is that the Chicago-land weather lead to the rough floors. The seller has also mentioned that the rockers and quarters also suffer from rust, but it is unclear what the exterior rust looks like overall. Would you take on this classic convertible?

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Comments

  1. Tooyoung4heyday Tooyoung4heydayMember

    Would make a sweet cruiser if someone had the funds. For those who made it to the MCACN this year shouldve seen this gorgeous custom.

    Like 12
    • Bud

      Definitely a poly motor, not a hemi. Through 54 the Windsors only came with 6 banger Spitfire motor. In 55 the poly motor replaced the Spitfire 6.

      Like 3
    • Will Fox

      Your photo is the Imperial Chrysler never built in `55. There was no Imperial cvt. after 1952 until the `57 models. This is a beautiful “what if” someone built, and it looks convincing. I’ve seen photos of this car before; this was no small feat to build!!

      Like 0
  2. Chinga-Trailer

    Is that a one barrel carburetor strangling the Hemi?? Talk about mixed messages!

    Like 0
    • Beatnik Bedouin

      Naw, it’s a Carter two-barrel, Chinga-Trailer. Hemis look a bit under-dressed without a 6-71 and bug catcher on top…

      Like 0
  3. hatofpork

    Martin and Lewis drove a red ’56 New Yorker convertible in Hollywood or Bust. Different grille (possibly other differences). This would be amazing for anyone who can afford the restoration.

    Like 1
  4. Dargon

    It Does appear to be a One Barrel, which would dictate that the engine though a V8 is Clearly of Relatively Small Displacement. Probably a 300 or 305. Chrysler made a Huge range of Her V8’s over the years. They were the First to experiment with the hemispherical cylinder head.

    Like 0
    • Will Fox

      Correct. This is NOT the 331 C.I. Hemi; it’s the 301 poly-head V8 that was standard on Windsors. The Hemi was standard on New Yorkers, Imperials, and of course, the C300.

      Like 0
  5. Gaspumpchas

    wow. As you can see these are drop dead gorgeous done. Hope someone can do her up. Good luck to the new owner!!

    Cheers
    GPC

    Like 1
  6. Shane Bates

    How did a 55 Windsor end up with a Hemi engine? Proper engine would be a 301 Spitfire.

    Like 0
    • Will Fox

      It didn’t. It IS the 301 poly-head Spitfire.

      Like 0
  7. Bob Snyder

    Windsor’s do not have Hemi engines and that doesn’t look like a Hemi in this one.
    331 CI Polyspheric motor is what it should be and what it looks like

    Like 1
    • Will Fox

      301 cubes; not 331. That was the hemi.

      Like 0
  8. David Zornig

    The original Craigslist ad does not mention Hemi.
    My gut says it is a 301 Spitfire.
    The engine photo is not wide enough to determine it.
    From what I’ve read, the 331 Hemi was only available in New Yorker and the 300 models in `55.

    Like 1
    • Will Fox

      ..and on Imperials.

      Like 0
  9. Maestro1

    If I had the room and the time I’d jump on it. Very elegant Chrysler, deep pockets required, worth doing.

    Like 1
  10. Tiger66

    The Windsor had the poly-head engine, not the Hemi.

    Like 1
  11. Del

    Very rare. Never seen one before.

    Write up says floor rust in cabin but I do not see any and carpet was pulled to show this. Trunk has perforation.

    Nada says 14 grand low and 44 grand high retail.

    Seller says Hemi but posters contesting that. No good pics to prove either way.

    This is another non runner that owner is hoping to cash in on. Price to high

    Like 1
    • David Zornig

      Except the Seller does not say Hemi.
      The writer of the article said that.
      Click on the Craigslist ad, and there is no mention of Hemi.

      Like 1
  12. DETROIT LAND YACHT

    A beauty absolutely worth restoring.
    15K is a tad ambitious…but someone might get there.

    Like 0
  13. David Zornig

    Just got an e-mail back from the seller.
    “The engine is a 301 not a Hemi.”
    The author should update the article accordingly.

    Like 2
  14. stillrunners

    Vary low production on these coverts makes them seldom see and if y’all can get past that carb…you can see the scalloped valve covers of a Spitfire Poly.

    Like 1
  15. David Zornig

    Well apparently it is a flipper.
    More pics here, and the price was originally for 2 cars from the previous seller if I’m reading this right.

    http://topclassiccarsforsale.com/chrysler/475682-1955-chrysler-windsor-convertible-amp-1956-chrysler-new-yorker-sedan.html?fbclid=IwAR0xaf8AhW7IXbbzrYz_3tLtTjGA2UTdHlV9A-e3V8gf7a8QGNfL7OdsZP4

    Like 2
  16. Jack G.

    Chrysler produced 1,395 Windsor Deluxe convertibles in 1955. The base price was $3,090, and shipping weight was 4075 lbs. The 301 Spitfire Poly put out 188 hp.

    Like 1
  17. Bruce Fischer

    I miss my 56 Chrysler Windsor.She had the 331 motor.It would cruise down the interstate at 75 M.P.H. with no problems at all.Bruce.

    Like 0
  18. Del

    Bruce….it should be able to cruise all day at 85 MPH

    Like 0
  19. PatrickM

    With all these knowledgeable comments, it leaves one with the knowing that I shall not purchase said, mis-informed trick. On to the next car.

    Like 0

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