1958 Cadillac Series 75 Fleetwood 9-Passenger Sedan Limousine

Playboy Club, Air Conditioned, California Car

This Rare Cadillac Fleetwood has SOLD
1958 Cadillac Fleetwood Limousine for Sale

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1958 Cadillac Series 75 Fleetwood Sedan for sale in Sonoma California. The story has been passed along from it's previous owners that the car was used in the 1960's as the official car at The Playboy Club in San Francisco. While we currently have no documentation to support this claim, it does make for a pretty cool story. You'll see that the Playboy insignia was added to the fins and as you might imagine this is definitely a conversation-starter. Only 804 Series 75 8-passenger 4-Dr Sedans were built by Cadillac and it is estimated that only around 80 still exist today.

Perhaps a Playboy historian could close the loop and verify the provenience. The current owner reached out to Playboy Enterprises and in their response stated the "records of the Clubs Division had been warehoused for nearly 20 years and are at this time inaccessible." Wouldn't that be something when they finally became available to find a photo of Hugh Heffner with this cool old Fleetwood?

This Series 75 was delivered new factory finished in Cheviot Gray and equipped with EZ Eye Glass, Power Vent Windows, Heater and Remote Trunk Lock Release. In addition, it has a vintage Allegro Mark IV air conditioning unit that blows ice cold.

The current owner purchased the car in white as it would have been since it's days at the Playboy Club. The exterior was professionally restored; stripped to bare metal and treated to a stunning, high-quality exterior restoration. It included most items being re-chromed, new weather stripping, molding trim, etc.

The seating is the same as when purchased though the headliner and rugs have been replaced. The trunk was carpeted and finished and the jack and spare are present. With exception of the clock and radio/power antenna, the gauges, lighting and accessories are all in good working order.

This Fleetwood starts; runs and drives beautifully! It's 365 cubic inch 310 hp V8 motor is in excellent running condition. The transmission has been rebuilt and shifts as it was designed to. The mechanics have been meticulously gone through assuring comfortable cruising and reliability. It has been continuously restored and maintained with excellent brakes, shocks, suspension; rebuilt transmission, restored fuel and cooling systems, electrical and a list too long to go through here. Over $50,000 in documentation will be sent along to the new owner. Click here for a current appraisal report.


  • 365 Cubic Inch 310 Hp V8 Motor
  • 4-Barrel Carburetor
  • Power Brakes
  • Power Steering
  • 3-Speed Automatic Transmission
  • Power Windows
  • Power Vent Windows
  • Air Conditioning
  • Heater
  • E Z Eye Glass
  • Factory 15" Wheels W/Polished Wheel Covers
  • 235/75-R15 Wide White Wall Tires
  • Remote Trunk Lock


  • Paint Code: 14 - Cheviot Gray, Trim
  • Code: 80 - Grey/Gray, Style: 58-7523X
  • Body: 420, ACC: H E S N
  • This Fleetwood represents an interesting opportunity to own a rare, still under-valued classic Cadillac and with eventual availability of it's currently alleged historical provenience, could prove to be an investment with some still-undiscovered upside.

    Thank you for visiting!

    VIN# 58R050896

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    1958 Cadillac Fleetwood Limousine for Sale
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