Chrysler Corporation’s dramatic new styling caught a lot of attention for 1957. Unfortunately, build quality for those gorgeous machines was spotty, and that reputation combined with an almost-industry-wide sales dip for 1958 means that finding a nice Chrysler from that model year is an uncommon treat. This nearly immaculate Windsor hardtop underwent a big change for 1958, although it’s tough for a casual fan to tell. The Windsor now shared a platform with Dodge, including its 122-inch wheelbase (compared to the 126-inches of other Chryslers). That means that the front sheet metal was built to match up with the Dodge body, and Chrysler did a nice job; it’s not apparent until you look at a Saratoga that something’s a little different. These days, few will care that your Chrysler is based on a Dodge when you’re driving around with all four windows rolled down in your ’50s spaceship. This beautiful Windsor is for sale on craigslist in Orange Park, Florida, and the ever-reliable T.J. sent it our way for a closer look.
I’ve always been fascinated by Chrysler’s engine program in the 1950s; it takes a cheat sheet to keep up. In 1958, Dodge used the old flathead six, the 325 cubic-inch Dodge Hemi, and two versions of the new wedge V8: 350 and 361 cubic inches. Even though the Windsor was based on a Dodge, however, it used a Chrysler 354 cubic-inch “Poly” V8, which is seen in our featured car. With a Carter BBD two-barrel carburetor, it made 290 horsepower, 20 less than the four-barrel 354 in the Saratoga. Plain as day, right? The engine compartment is nicely detailed on this Windsor, and you can see the fascinating Kelsey-Hayes “accordion-style” brake booster at the top of the picture. It sits right on top of the master cylinder, which makes adding fluid an interesting process.
The seller claims that the car is a 40,318-mile original, and the interior looks as if we’ve accidentally awakened in 1958 (aside from perhaps the dashboard upholstery). Chrysler used pushbutton drive for the Torqueflite, with the selector in a handy place to the left of the steering wheel, out of reach of nefarious passengers.
In its handsome Bamboo Yellow and Ermine White two-tone paint, nobody will care these days that you didn’t spring for a Saratoga or New Yorker; they’ll be too busy ogling you and commenting on your unimpeachable taste in cars. Nice Forward-Look Chryslers don’t come cheap, and the seller is asking $42,500. That’s out of reach for many of us, but if you want a solid ’57 or ’58 Chrysler hardtop, you just don’t have that many options. I can’t imagine that this one will stick around for long.
Driving this in my hood would definitely make a bold statement.
Sweet Windsor wow.
“Spotty build quality” is sort of the elephant in the room for this era Chrysler products, sad to say. How did this one survive looking so nice?
The front end (basically Dodge) was also used for DeSoto entry level Firesweep. LIke Firesweep it was actually shorter. While I am a fan of Exners finned fantasies, I always felt this side treatment was strange. But many two tones of the time were strange 🤪. As noted build quality was an issue, making this a rare survivor. BTW, I believe WINDSOR was retired after 59? Along with SARATOGA while only NEW YORKER remained at the top of the line.
The Windsor lived on after 1959. My dad had a 1960 Windsor 2-door hardtop. With the introduction of the Newport series in 1961, the Windsor became the mid-level offering, replacing the Saratoga. The Sport 300’s replaced the Windsor in 1962, except in Canada.
If it Is too much money! Go find another one!
Always wanted one of these when they were newish.
A pleasant color combo, and the visual flow of the body and trim defies Chryslers’ tendency during those years to combine way too many angles and way too much chrome. Just my opinion. This one looks sweet to me.
Like Joe says: Go find another one!
Many of us today seem to prefer the lower end models simply because they are less decorated with chrome. We’ve become so accustomed to the simplicity of modern cars.
Parents had a 57 Saratoga. Beautiful car that had lots of power.
If George Jetson was earthbound in 1958, this is the car he would have driven.
Everything about the design execution is fine, EXCEPT for that front bumper! Truly looks like an afterthought from something laying around in the parts bin.
If I had a late 50s Chrysler Corp. collection (any other fans of alliteration here?), this Windsor would be mine. It could sit near the pinnacle which would be a ’57 DeSoto Adventurer Hardtop.
One of the nicer of the Forward Look cars. Helped out by the new headlamp regs.
I don’t care ! I love this car. I wish I could afford it.