Golden Lion V8: 1959 Chrysler Windsor Coupe

Chrysler’s Windsor nameplate stretches back to 1939 when the model was launched to occupy a niche below the New Yorker. By the mid-1940s, the Windsor accounted for 63% of Chrysler’s sales. Virgil Exner’s “Forward Look” brought fins to its… more»

True Barn Find: 1955 Chrysler Windsor DeLuxe

By the mid-fifties, design guru extraordinaire Virgil Exner was calling the shots at Chrysler when it came to styling, with the new look of the 1955 Windsor DeLuxe credited to his skills along with the rest of the brand’s… more»

Dusty Red Ragtop: 1948 Chrysler Convertible

Doesn’t this look like the quintessential barn find? A stylish 1948 Chrysler Convertible with just the right amount of dust and patina on its faded red paint and tan canvas top. The listing by the seller as a “1948… more»

Same Family Since New: 1956 Chrysler Windsor

From 1939 through most of the 1960s, the Windsor was Chrysler’s “everyman” car, an automobile for those who wanted a Chrysler but weren’t ready to spring for a New Yorker or Imperial. This 1956 Windsor 6-passenger station wagon was… more»

Semi-Hemi! 1955 Chrysler Windsor Deluxe

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»

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»

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»

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»

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»

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»

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»

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»

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»

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»

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»

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»

Barn Finds