BaT Bash: 1941 Chrysler Highlander Convertible – SOLD!

by | Apr 2023 | Craigslist ClassiFINDS, Topless Thursday

(To stop the slideshow and expand the pictures, click on the current photograph below)

April 26, 2023, Update – We confirmed the seller of this “Classifind” deleted their listing, so we’re now able to call this one “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.

Contrary to popular opinion, not everything offered on Bring a Trailer (“BaT”) sells at record prices. In fact, twenty percent of the rides offered do not meet their reserve price.  While the excellent pictures of this Yellow 1941 Chrysler Windsor Highlander convertible last listed in April 2023 on Craigslist in Santa Barbara, California, are what first attracted us to the car, a bit of research revealed the sellers managed to get their car listed as Lot #87136 on BaT Auctions in October of 2022. Unfortunately, with a high bid of only $20,018, it did not meet the reserve price.  Reported to be family-owned for 37 years, the seller’s father bought the car in 1985 and completed a frame-off restoration of what appears to be a well-preserved example. Many of the dashboard parts are considered unobtanium these days, so this Chrysler appears to be a nicely restored example.  The only downside for some may be that the seller’s father elected to paint the car yellow instead of its original shade of red that matched the Tartan plaid interior.

Last offered for $30,000,, the analytics and search engine for the collector car market, confirms the ask is in line with this guide’s summary for Chrysler Windors of all body and trim styles produced between 1940 and 1941.  By clicking on the green dots in the graph below, you can navigate to each comparable car sold as a way to help you evaluate the price of the truck featured here:

As a second data point, the downloadable 2023 Old Cars Big Book reveals the seller’s ask falls between this guide’s #2 Very Good” estimate of $28,000 and its #1 “Excellent” appraisal of $40,000.

For the 1941 model year, Chrysler offered its entry-level, inline-six-powered Series 28 line in three trim levels. The lowest level was known as the Royal.  Chrysler marketers labeled the mid-trim level Windsor.  Topping the Series 28 line was the Windsor Highlander.  The most striking feature of the Highlander models was the combination of leather and Tartan plaid interior. Additionally, Highlander models featured distinctive marbelized Bakelite-style dashboard trim pieces. Other than the distinctive interior, Highlanders relied on Chrysler’s ubiquitous 108 brake horsepower, 241.5 cubic inch L-head inline six-cylinder engine, three-speed Fluid-Drive transmission, coil-spring independent front suspension, live rear axle with semi-elliptical leaf springs, and four-wheel hydraulic drum brakes.

The Grandpas Garage YouTube Channel features this video giving the perspective of what it’s like to drive a 1947 Chrysler equipped with Fluid Drive:


This 1952 Ford F-1 Pickup appears to be a nicely restored low mileage survivor that has held up well.

If you are serious about buying this Chrysler Windsor, you can start the conversation by contacting the seller through the information provided in their Craigslist ad, when you connect, please remember to mention you saw their Highlander-trim convertible featured here on Good luck with the purchase!

Here’s the seller’s description:

“For sale is a gorgeous 1941 Chrysler Highlander convertible with the Scottish plaid upholstery “Highlander” package from that era. This is more than a Windsor, it’s a rare Highlander! Beautiful mottled red bakelite/catalin trim dashboard original to the car. Elegant and eye appealing cream paint job.

Older restoration leaning into #2 quality. It’s been garaged for about 10 years since last drive around town. We’ve started it up on occasion regularly just to idle. Prior to storage, the car drove around town as pleasant as can be (have not tested on freeway or long distance drives). Transmission is a clutch with the “Fluid Drive”. Restored are; engine rebuilt, transmission serviced, brakes done, fuel system rebuilt, gas tank brand new, electrical rewired, chrome re-chromed, EVERYTHING done so the previous owner could enjoy a nice drive. (Except the radio, that’s in place but never tested or serviced.)
There’s light age showing. Minor chips in paint from normal use; some peeling in chrome here and there on bumpers hard to see; car presents itself well. Current as of today drive state largely untested; drove when last garaged.

We’re selling it because the elderly owner no longer drives. Here’s your chance at a unique, distinguished convertible with the blue and red plaid upholstery and BAKELITE dashboard you won’t see anywhere else.


Show or go: What would you do with this restored 1941 Chrysler Windsor Convertible?  Please comment below and let us know!


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