Some classics emerge from hiding and seem to tick many of the right boxes for potential buyers seeking a vehicle to restore or preserve. This 1955 Chrysler Windsor is a perfect example, having spent over a decade in dry… more»
Windsor
Mar 1, 2025 • For Sale • 12 Comments
Marvelous Mopar: 1941 Chrysler Windsor Convertible
The 1940s Chrysler product portfolio offered a near-perfect aspirational ladder for would-be buyers, from the Royal to the Imperial – all aptly named. The Windsor was introduced in 1939, a top-level trim option sitting above the Royal in its… more»
Feb 15, 2025 • For Sale • 27 Comments
1 of 2700 Built: 1956 Chrysler Windsor Town and Country Wagon
In 1956, station wagons continued their popularity across America for a number of reasons. The nation was ten years into the Baby Boom era, more families had moved to the suburbs, the nation’s economy was good, and station wagons… more»
Sep 17, 2024 • For Sale • 7 Comments
Work In Progress: 1959 Chrysler Windsor Convertible
In the pantheon of ChryCo head stylist Virgil Exner’s over-the-top designs, today’s find of a 1959 Chrysler Windsor, courtesy of T.J., is pretty tame by comparison. Sure, it has memorable tailfins, which many automotive designs possessed in ’59, but… more»
Sep 14, 2024 • For Sale • 23 Comments
Cherished: 1947 Chrysler Windsor Club Coupe
Chrysler’s Windsor nameplate was introduced in 1939 on a full-size platform with a blend of luxury interior appointments and an economical engine. The car retained its middle-of-the-road niche after the war, with the New Yorker and the Imperial occupying… more»
Jul 8, 2024 • For Sale • 14 Comments
One Owner Wagon: 1956 Chrysler Town And Country
Chrysler gave its full-size cars a major facelift in 1955, which included the Imperial which was spun off into its own division. The styling gave a prelude to what was coming with the bold “Forward Look” approach of the… more»
Feb 14, 2024 • For Sale • 13 Comments
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»
Jan 7, 2024 • For Sale • 10 Comments
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»
Oct 28, 2023 • For Sale • 12 Comments
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»
Jul 9, 2023 • For Sale • 18 Comments
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»
Feb 26, 2023 • For Sale • 11 Comments
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»
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 • 8 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»
