Doctor’s Car: 1958 Cadillac Sedan De Ville

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Some of us can remember when cars all starting four headlights. Plymouth started in 1957 and GM and Ford followed in 1958. This Cadillac listed here on eBay in Williston, Florida was owned by a doctor who quit driving it in 1971. The owner has had it mechanically restored, including rebuilding the engine, brakes and exhaust. The rest is completely original.

right rear above

It’s a nice 20 footer but the chrome and paint do need help. There are no obvious signs of rust.


The bottom looks nice. It was power washed, degreased and undercoated. Hopefully, the undercoating is not hiding rust.


The engine bay certainly looks nice. Hopefully the engine rebuild was done well.

inside front

Inside, it looks soiled and worn, but original. A good cleaning would go a long way here.


This old Cadillac needs a lot of cosmetic help, but it could be a nice driver as it is if the mechanicals were done well. The owner has spent too much money on the old Cadillac and is no doubt hoping to recover his investment. Bidding at this time is at $7,900 with 3 days left and the reserve not met. Is this Cadillac worth much more? Are there any Cadillac fans who might love this old sedan?

Auctions Ending Soon


  1. Fred W.

    Apparently they spent $10K on the mechanicals plus the price of the car, for a 4 door HT. Prospect of break even doesn’t look good for the seller.

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  2. Ed B

    Hi David:
    I guess a local pastor (description of original owner on eBay) could be a doctor (as described in your write-up) but how did you conflate the two professions? Many thanks.

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    • Michael Houston

      I don’t know about the US but in the UK many ministers (pastors) are Doctors of Divinity. He could also be a PhD doctor in an unrelated subject.

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    • Roselandpete

      No doubt a gift from a wealthy member of his flock.

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  3. Dan

    New Jersey plate on the front, Florida plate on the rear.Hmmm…..

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  4. Luke Fitzgerald

    Wind up windows – never seen one this late with them

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  5. Vince Habel

    57 Plymouth did not have 4 headlights.

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  6. G 1

    Plymouth and Dodge did not have dual headlights in 57. Chrysler and Desoto did.

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  7. Jim Benjaminson

    Always loved the ’58 Cadillac – too bad its not a Fleetwood 60 Special.
    Should note the 57 Plymouth-Dodge had single headlights with a closely mounted parking light to give the illusion of dual headlamps. Not all Chrysler’s or DeSoto’s had dual headlights – it depended on which state they were sold in as some states had not adopted the dual headlight system into their laws. By 1958 everyone was on board. State laws prevented many cars from going to sealed beam headlights in 1937 – took until 1940 to get all 48 states on board.

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  8. JDR

    57 Chrysler products did not have four lights…they had dual lights. I believe four headlights were not legal until ’58?

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  9. Luki

    “No paint work ever”.
    The left front fender and drivers door appear to be darker than the rear of the car.
    The hood and trunk look lighter than the rest.
    I’m thinking there was some paint work done along the way

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  10. Rick

    Lincoln Premiere and Capri had 4 headlites in ’57 in all states – a 6014 High/Low beam stacked on top of a 4000 Hi-beam

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  11. Rob

    Right in my backyard! Too bad I’m poor or I would scarf this up. I love the old Caddys.

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  12. William H

    I had this exact car in black. Bought it unseen for $327 thinking I was going to get a shell. Imagine my surprise when I pulled up to find a car in great shape with only dent in the rear passenger door. The guy I bought it from was the 2nd owner. He had pulled the front end off the engine to replace a bad water pump but never got around to it. Talk about spacious… you could probably fit 8 full grown men in the trunk. Probably the #1 car I wish I’d never gotten rid of. Never could get a straight answer from the seller about his peculiar asking price on the car.

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  13. Eric Dashman

    The 57 Plymouth did not have 4 headlights. It only looked like it did, but the inner light was a parking or turn signal light. Same for the Dodge and Desoto. As to Chryslers and Imperials, I know for sure that there were single headlight Chryslers and Imperials in 57 and went to the dual setup in 1958. Perhaps Chrysler made a mid-year switch because a Google search returns both types. The 300C may have had dual headlights. The 1957 Mercury Turnpike Cruiser definitely had dual headlights. 1958 was when most switched to the duals, including Ford’s complete ruination of the gorgeous 1957 model, both front and rear. What were they thinking? Ugh.

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  14. geezerglide85

    Luke, regarding your comment about the crank windows. Back in the late ’70’s I remember a ’63 caddy on a small car lot in town that was a complete “no option” car. It wasn’t a Sedan deVille but I think it was a Calis (no model name on it). The car had crank windows, manual seats, no a/c, and no radio. A real curiosity. It sold for $500. and was in great shape. Broke my heart, I saw it around town and within a year it was beat to death.

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    • Roselandpete

      Sounds like a Calais alright. I guess some would prefer a stripped down Caddy just to have a Caddy rather than a loaded 98 or 225.

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  15. L.R.Foster

    1957 DeSoto, Chrysler, and Imperial had two headlights standard at beginning of year with 4 lights optional except for Desoto Firesweep which used a version of ’57 Dodge front end with 2 lights only for the full year. My Aunt bought a New Yorker convertible the first week they were in…with 4 headlights. The dealer was a friend of our family, he said he was ordering all the Chryslers and Imperials with 4 lights unless a customer chose otherwise. Some states still had laws preventing 4 lights. Nash went ahead with 4 light system and no one complained. The ’57 Lincoln had high beam and low beam in the upper headlight, the lower light is slightly smaller, was a driving/fog light turned on with a switch on the left side of the steering column, for use as fog lights you put headlight switch in parking light position which lit lower lights and those gorgeous huge parking lights front and rear. It worked well, I had 3 ’57 Premieres, two coupes and a convert. The Mercury’s were designed for 2 lights, but managed to stick four on with a casting. The only GM car with 4 lights in ’57 was the Eldorado Brougham, I had a black one with an aggressive automatic headlight dimmer, it would wait until a car was so close it couldn’t respond and turn the brights on, blinding them. I’ve had the pleasure of having over 1,000 cars pass through my hands, and enjoyed most all of them in some way. It gives me a unique position of experiencing most every American and quite a few foreign ones built from 1949 through the 70’s. Ever have an Armstrong-Siddeley Star Sapphire? Most cars had 4 lights in 1958. Unfortunately Studebaker and Packard put ungainly pods on the front fenders for quad lights, still, I got used to the styling on the President Starlight coupe, and Packard sedan I had, more unfortunately even on the 2 headlight Champion series the pods were there. When they introduced the Scotsman, it was straight ’57 body with the only chrome being bumpers and door handles…and 2 headlights. Thankfully they didn’t bugger up the hawks, and left them at 2 headlights. For 50 years I had a auto restoration/detail shop and most of the dealers in town would have me do cars for the showroom. I saw many unusual cars special ordered over the years. One very wealthy rancher wanted No power accessories or automatic trans, no radio or clock even, on his new 1968 Cadillac Fleetwood 60 Special, (although his wife was very insistent it have A/C and heat ). They had to adapt a 4 speed standard trans. I prepped it for the dealer. It cost way more than a fully loaded Fleetwood. The dealer said he traded every 3-4 years, with roll up windows and nothing but the A/C/ heater unit in his cars the dealer said they usually used them for body and interior parts when traded in, no one wanted them.

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  16. RoselandPete

    WOW! 1,000 cars…

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