Kool Kustom: 1955 Chrysler Windsor Roadster – Sold?

by | Jul 2021 | Classifinds, Topless Thursday

September 16, 2021 Update – We just confirmed the listing for this “Classifind” expired, so with no replacement found we’re assuming this ride “Sold?” While this one got away, please reach out either by email or call us directly if you’d like to be informed when we come across something similar.

August 15, 2021 Update – The seller of this topless Chrysler Windsor just lowered their asking price by one thousand to $17,000.

July 30, 2021 Update – The day after we first featured this Chrysler Windsor Roadster, the seller changed the price from “$1 Trade” to $18,000.

The current caretaker of this 1955 Chrysler Windsor Roadster we first came across in July 2021 on Craigslist in Trumball, Connecticut calls his heavily-patina class “Rockabilly Style” judging by the other classics parked in his driveway, there’s no doubt in our minds he knows what he’s talking about.  When compared to the custom ’47 Oldsmobile featured elsewhere today, it’s easy to see how much custom car tastes have changed over the past thirty years. We’re calling this car a “Roadster” as this car started life as a hardtop that’s had its steel roof removed; consequently, there is no top mechanism in place.

Here’s the seller’s description:


Kustom 1955 Chrysler Windsor Convertible w/ 301 Spitfire engine and auto transmission.

Very unique Rockabilly style classic w patina. Runs and drives, could use a brake adjustment. Car turns on all the time and cruses like a 66-year-old car with some creaks here and there.

Engine runs nice and transmission shifts smoothly. Definitely NOT an LS1 framed swapped restomod!

The exterior looks solid and free from any rust holes. All the exterior trim is there, even has a rear bumper guard (not installed). The interior is very presentable. Some of the dash components don’t function, like the fuel and speedometer gauges. Signal lights are not working, so stick your arm out like the old days.

Has previous floor repair, frame and trunk are solid. Has painted 15 inch steelies w thick whitewall tires and good thread.

Factory dash installed automatic shifter, no parking gear. Just put it in neutral and pull the ebrake, which is also on the dash.

All glass is intact except for the front driver’s side window. It is present, but cracked.

This is a custom convertible, so there is no top mechanism. Everything was nicely done. Bag it, pinstripe and drive it dirty. Paint it or leave it as is.

Again, this is a head turning, 8 cylinder cruiser w Viva Las Vegas attitude. Fun classic for weekend cruising and to stand out in the crowd of everyday Mustangs and Camaros.

It had a clear California title, but now is currently registered in Connecticut. It will be sold with a transferable CT registration and bill of sale.

Connecticut does not issue titles for classic vehicles, please verify this through DMV website for confirmation. There is a picture of the current reg (address blocked) and the vin plate.

Looking for running/driving trades (no projects). Interested in 40s-60s GM or Mopar coupes or pickups (no Fords). I appreciate Fat fenders, fins, body dropped, bagged, ragtops etc.

Show or go: what would you do with this Chrysler Windsor?  Comment below and let us know!

  1. Kool Kustom: 1955 Chrysler Windsor Roadster – Sold?

    I now own it

    • Kool Kustom: 1955 Chrysler Windsor Roadster – Sold?

      Congratulations on the purchase, Frank! If desired, please send us pictures of you with the ’55 Windsor https://www.guyswithrides.com/guys-with-their-rides/ and we will post them in our “Guys With Their Rides” section. We’ll send you some free GuysWithRides.com merch for doing it!


Submit a Comment

Your email address will not be published. Required fields are marked *