Chrysler introduced all-new cars for 1955 and would dub them the “100 Million-Dollar Look” (in advance of the “Forward Look” machines of 1957). They pared down the number of models to three: Windsor, New Yorker, and 300, with the… more»
Windsor
Feb 5, 2023 • For Sale • 16 Comments
Needs Nothing: 1961 Chrysler Windsor
It is common to look at classics with more than six decades under their belts and begin to tally up what it will cost its new owner to return the car in question to a physical, mechanical, and cosmetic… more»
Feb 4, 2023 • For Sale • 25 Comments
No Reserve, No Motor, No Tranny: 1946 Chrysler Windsor 4-Door
I’ve always liked the bulbous, brawny styling and “presence” of the 1946-1948 Chryslers. And this one’s been in a barn for 50 years and is being sold at No Reserve to help settle an estate. Hopefully, Ken the seller… more»
Sep 25, 2022 • For Sale • 7 Comments
Restored then Parked: 1950 Chrysler Windsor
Chrysler first made the Windsor in 1939 as a full-sized luxury car with an economy motor for those who couldn’t quite rustle up the dough for a New Yorker with its straight-eight. Production was interrupted during the war but… more»
Aug 13, 2022 • For Sale • 17 Comments
1 Of 10 Remaining? 1959 Chrysler Windsor Convertible
How many examples of any particular vehicle are still with us is usually a loosely calculated estimate, but the seller of this 1959 Chrysler Windsor Convertible has done a reasonably credible job of consulting with other owners of these… more»
Jul 26, 2022 • For Sale • 9 Comments
Fabulous Fins! 1957 Chrysler Windsor
The Windsor debuted in 1939 and would remain in the Chrysler U.S portfolio through 1961. Typically, it was the entry-level model that led the way to the more luxurious New Yorker (and the Imperial, which didn’t always carry a… more»
Jun 27, 2022 • For Sale • 31 Comments
Sitting for 40 Years: 1948 Chrysler Windsor Business Coupe
When was the last time you saw one of these? Yeah, I can’t remember either. The Chrysler Town & Country with its beautiful and unique wood trim gets all the attention, but this 3-Passenger Coupe with its one bench… more»
Dec 24, 2021 • For Sale • 8 Comments
1 of 1,392: 1955 Chrysler Windsor Deluxe Convertible
1955 was a watershed year for Detroit in regards to styling, new engines, dazzling colors and interiors, and sales. A record year with almost eight million automobiles sold. By comparison, the 1954 Chrysler looks frumpy compared to the all… more»
Nov 15, 2021 • For Sale • 17 Comments
Rust-Free Stunner: 1955 Chrysler Windsor DeLuxe Hardtop
Cars from the 1950s were renowned for two things. Many were stylish and glamorous, while many could dissolve like a soluble Aspirin at the merest hint of moisture. This 1955 Chrysler Windsor Hardtop may be stylish, but it has… more»
Sep 12, 2020 • For Sale • 10 Comments
Last Registered In ’86: 1956 Chrysler Windsor
The 1955-56 Chryslers had the “hundred million dollar look,” according to the marketing pundits. These were large, graceful cars that had a more dynamic appearance than the competition. This certainly was true of the hardtop coupes, like the 1956… more»
Mar 14, 2020 • For Sale • 31 Comments
24k Original Miles! 1956 Chrysler Windsor
The current owner of this 1956 Chrysler Windsor isn’t the car’s first owner, but he has been its custodian for more than 40-years. Now aged in his 80s, he has decided that the time has come for him to… more»
Jan 26, 2020 • For Sale • 19 Comments
Dusty, Not Rusty: 1957 Chrysler Windsor
You know that a car has been sitting parked in a barn for some considerable time when the dust is so thick that it’s impossible to determine what color it is. That’s the story with this 1957 Chrysler Windsor…. more»
Sep 29, 2019 • For Sale • 12 Comments
A Whole Lotta Coupe: 1948 Chrysler Windsor Coupe
When K. T. Keller took over Chrysler after the passing of the company’s founder, he made it clear that styling was to be conservative. He insisted that a man should be able to comfortably wear a hat in a… more»
Sep 26, 2019 • For Sale • 18 Comments
Spotlessly Clean: 1950 Chrysler Windsor Newport
If you parked this green 1950 Chrysler Windsor Newport in your driveway, it would probably be enough to turn your neighbors green with envy. It is a beautifully presented car that I think most classic car enthusiasts would like… more»
Jan 1, 2019 • For Sale • 24 Comments
One Family Since New: 1953 Chrysler Windsor DeLuxe
This 1953 Chrysler Windsor DeLuxe is a very nice car that appears to need only some very minor detail work to really make it stand out. It has spent its entire life owned by the one family, but they… more»
Dec 24, 2018 • Classifieds • 10 Comments
True Barn Find 1950 Chrysler Windsor
Located in Mossyrock, Washington, this 1950 Chrysler Windsor is a true barn find. Covered in light surface rust and layered in dust, this 35,000 mile car does have a clean title. Thankfully the price is not unreasonable either. It… more»
