1939 Cadillac Fleetwood Series 75 Convertible Coupe
Presentation
This 1939 Cadillac Fleetwood Series 75 convertible coupe is one of 27 produced and is said to have been delivered new in Seattle. It later underwent a three-year refurbishment and was purchased by the current owner in 2020. The car is finished in Kingston Gray with a brown convertible top over green leather and is powered by a 346ci V8 linked with a three-speed manual transmission. Equipment includes 16″ steel wheels with chrome hubcaps, dual side-mount spares, hydraulic drum brakes, rear occasional seats, a push-button AM radio, and an under-dash heater. This Fleetwood Series 75 is a CCCA Premier Senior National First Prize winner and is now offered on dealer consignment with literature, spare parts, and a clean Arizona title.
This 1939 Cadillac Fleetwood Series 75 convertible coupe is one of 27 produced and is said to have been delivered new in Seattle. It later underwent a three-year refurbishment and was purchased by the current owner in 2020. The car is finished in Kingston Gray with a brown convertible top over green leather and is powered by a 346ci V8 linked with a three-speed manual transmission. Equipment includes 16″ steel wheels with chrome hubcaps, dual side-mount spares, hydraulic drum brakes, rear occasional seats, a push-button AM radio, and an under-dash heater. This Fleetwood Series 75 is a CCCA Premier Senior National First Prize winner and is now offered on dealer consignment with literature, spare parts, and a clean Arizona title.
The car left the factory finished in Kingston Gray (62) and has been repainted. Exterior details include running boards, a split windshield, and a brown soft top that stows under a matching boot. The turn signals do not work, and there are paint touch-ups and chips. A CCCA Premier Senior National First Prize plaque is affixed to the right side of the car, while a Cadillac LaSalle Club plate is on the opposite side.
Body-color 16″ steel wheels feature chrome hubcaps and are mounted with Hercules radial whitewall tires. Dual spares are mounted in the fenders under hard covers topped by mirrors. Braking is provided by hydraulically actuated drums at each corner. Suspension comprises an independent coil-spring front setup and a rear semi-floating axle with semi-elliptical leaf springs.
The cabin houses a front bench seat and flip-down rear occasional seats that have been reupholstered in green leather. Interior appointments include a woodgrain dash and door caps, a non-working analog clock, a push-button AM radio, rear robe ropes, and an under-dash heater.
The steering wheel fronts a 110-mph speedometer and auxiliary gauges. The five-digit odometer shows 4k miles, and total mileage is unknown.
The 346ci Monobloc L-head V8 was factory equipped with a single-barrel Stromberg carburetor and was rated at 140 horsepower when new. The car retains a six-volt electrical system with a generator. A cut-off switch has been added.
Seller Video
Bids & Comments
Aug 14, 2026 · 15:55
Interesting how the universe speaks sometimes...
With this auction running through this weekend, which happens to be same time as the Pebble Beach Concours d'Elegance, it's entirely fitting that Mr. John Milliken of Westlake Village completed the restoration of this Cadillac in 1994 and showed it at Pebble Beach Concours d'Elegance that same year.
An award winning car, incredibly rare, and ready for its next caretaker.
We look forward to your continued questions and comments throughout the weekend on this beautiful Cadillac.
With this auction running through this weekend, which happens to be same time as the Pebble Beach Concours d'Elegance, it's entirely fitting that Mr. John Milliken of Westlake Village completed the restoration of this Cadillac in 1994 and showed it at Pebble Beach Concours d'Elegance that same year.
An award winning car, incredibly rare, and ready for its next caretaker.
We look forward to your continued questions and comments throughout the weekend on this beautiful Cadillac.
Harrycad
Bid
Aug 14, 2026 · 15:48
Bid in the amount of $29,000
Aug 14, 2026 · 02:39
The very car that I learned one could actually drive an "old" car (pre 1950's) I-5 Southbound, rainstorm, beer between my knees. THAT Cadillac is a peach! Thanks for the memory. Good Luck with the auction.
Aug 12, 2026 · 20:12
One of our favorite little details on this Cadillac is something you could easily overlook: the flip-down glass rear window in the convertible top, as seen in photo #147.
Even back in 1939, Cadillac wanted the clarity and durability of a real glass rear window, but glass obviously doesn't fold when you put the top down. Their solution was beautifully simple: the rear glass hinges down independently, allowing the convertible top to fold around it.
Sometimes the smallest features tell you the most about how thoughtfully these cars were designed.
It's such a clever piece of old-school engineering, and exactly the kind of detail that makes spending time around such a rare and timeless automobile so interesting.
Even back in 1939, Cadillac wanted the clarity and durability of a real glass rear window, but glass obviously doesn't fold when you put the top down. Their solution was beautifully simple: the rear glass hinges down independently, allowing the convertible top to fold around it.
Sometimes the smallest features tell you the most about how thoughtfully these cars were designed.
It's such a clever piece of old-school engineering, and exactly the kind of detail that makes spending time around such a rare and timeless automobile so interesting.
Aug 12, 2026 · 19:59
What a truly beautiful automobile!
Aug 11, 2026 · 15:03
@Jagbuxx Great question, and you're correct on the color code differences. We don't currently have much in the way of records, but we're working to see if we can get anything from the restoration.
Aug 10, 2026 · 16:00
On the body plate, code 817 should be grey leather. Green leather is coded as 816 as per the ‘39 color and upholstery book. Was this a deviation during the restoration? Is a copy of the original build invoice available?
Aug 10, 2026 · 14:25
@safarilang Check photo 75, that area has received a touch up. There are a couple of small nicks present that we would considered to be consistent with driving/touring.
James57
Bid
Aug 10, 2026 · 02:27
Bid in the amount of $28,000
Aug 9, 2026 · 20:00
Is there paint damage other than photo 59
Aug 9, 2026 · 19:07
Such a great driving video, I love how silently and gracefully it goes down the road 👌…just wonderful
safarilang
Bid
Aug 9, 2026 · 19:07
Bid in the amount of $27,500
Aug 9, 2026 · 15:51
Check out the driving experience in this beautiful Cadillac. The 346ci V8 delivers smooth, effortless power while the massive 141.3-inch wheelbase gives it that unmistakable big prewar Cadillac ride.
Top down, wind in your hair, floating down the road. This is one of those cars where the experience from behind the wheel may be even better than admiring it from across the parking lot.
Top down, wind in your hair, floating down the road. This is one of those cars where the experience from behind the wheel may be even better than admiring it from across the parking lot.
Aug 9, 2026 · 15:48
Check out the driving experience of this beautiful Cadillac.
Aug 9, 2026 · 12:56
@Seller: Thank you for your kind note.
It is I that is grateful to you for doing all of the heavy lifting ...while I'm watching from the comfort of my La-Z-Boy.
It is I that is grateful to you for doing all of the heavy lifting ...while I'm watching from the comfort of my La-Z-Boy.
Aug 9, 2026 · 12:55
@Seller: Thank you for the kind tag.
It is I that is grateful to you for doing all of the heavy lifting ... while I'm watching form the comfort of my La-Z-Boy.
It is I that is grateful to you for doing all of the heavy lifting ... while I'm watching form the comfort of my La-Z-Boy.
Aug 9, 2026 · 12:54
@Seller: Thank you for the kind tag.
It is I that thanks you ...for doing all of the heavy lifting ... while I'm watching in the comfort of my La-Z-Boy.
It is I that thanks you ...for doing all of the heavy lifting ... while I'm watching in the comfort of my La-Z-Boy.
Aug 9, 2026 · 11:08
Now that's a beautiful dashboard.
Note the spelling ASH | TRAY so that the double-width item could be integrated with the row of square buttons.
Note the spelling ASH | TRAY so that the double-width item could be integrated with the row of square buttons.
Aug 8, 2026 · 23:11
@Ranchero65 Very astute and appropriately named! This example definitely falls into the late Art Deco/Streamline Moderne styling with the sweeping lines throughout the styling.
Cadillac definitely understood the assignment with these as post-Depression and pre-war luxury motorcars. Gorgeous... or, shall I say handsome (nod to Art)... in presentation.
Cadillac definitely understood the assignment with these as post-Depression and pre-war luxury motorcars. Gorgeous... or, shall I say handsome (nod to Art)... in presentation.
Aug 8, 2026 · 22:47
Usually when cars are given names the owner tends to use a female name. But if I owned this I would name him Art, after my favorite pre-war designer: Art Deco.
Aug 8, 2026 · 22:40
One of 27 produced? Well, no wonder I've never seen one before!
Aug 8, 2026 · 18:36
My dear friend John Miliken performed the restoration on this Cadillac, back in 1994. It was so stunning that it was invited to exhibit at the Pebble Beach Concours, in the same class as JB Nethercutt and General Lyon. This is definitely a perfect car for touring and concours showing. John also added a Gear Vendor overdrive, allowing it to be activated with the quick flick of a switch under the dashboard. This makes it a 6-Speed!! Woohoo! Another friend of mine owns this now. He drove it last Fall on our local CCCA Mini-CARavan and it performed flawlessly! Let's hear it for Cadillac! Harry
Aug 8, 2026 · 16:53
Here's an interesting bit of perspective on the rarity here:
Cadillac produced 2,069 Series 75s across all body styles for 1939. Just 27 were Convertible Coupes like this one, and only five are believed to survive today. That's roughly 1.3% of Series 75 production.
To put the rarity into perspective: You can attend an awful lot of major concours, Cadillac gatherings, and collector-car auctions without ever seeing another one in person.
Some cars fill a space in a collection. This one punctuates it.
Cadillac produced 2,069 Series 75s across all body styles for 1939. Just 27 were Convertible Coupes like this one, and only five are believed to survive today. That's roughly 1.3% of Series 75 production.
To put the rarity into perspective: You can attend an awful lot of major concours, Cadillac gatherings, and collector-car auctions without ever seeing another one in person.
Some cars fill a space in a collection. This one punctuates it.
Aug 7, 2026 · 22:08
@David_P We had a 1938 Fleetwood four door not that long ago... much longer!
Aug 7, 2026 · 22:07
@Dollycat3 Thanks for always giving love to the cars we bring onto the platform!
Aug 7, 2026 · 22:06
@Hoppy18 A nice milestone... and this one is a special car. Thanks for being a great contributor!
Aug 7, 2026 · 19:47
This is the kind of automobile that reminds you how much artistry once lived in steel and chrome. A head turner, but more than that, a reminder of an era when luxury meant craftsmanship, not excess.
Aug 7, 2026 · 17:34
That's a long, long body for a 2+2.
Aug 7, 2026 · 15:41
@ClassicPromenade…..@hoppy18….thank you for the tags…👍…What an absolutely beautiful and rare Series 75 Convertible Coupe, it is an ultra-rare pre-war masterpiece. It combined a massive 141-inch limousine wheelbase and semi-custom Fleetwood coachwork with Cadillac's robust 140-hp L-head V8 engine. With only 27 convertible coupes were completed by Fleetwood for the 1939 model year, making it scarce even when brand new. Historians and registries estimate that as few as five authentic examples survive today, placing it among the most coveted collector cars of the pre-war era, I love the understated and elegant Kingston Gray with a brown convertible top over beautiful green leather interior, absolutely gorgeous 👍….…....@lincolnsandcaddies..
Aug 7, 2026 · 12:03
Beautiful car. The beginning of the end of this type of classic styling. Would love to own it, turn signals or not.
Aug 7, 2026 · 01:22
@Aridgerunner is correct. Buicks did, but Cadillac did not add them until the following year. Some buyers/owners installed non-self cancelling signals as an aftermarket, rear only.
Wade0
Bid
Aug 6, 2026 · 15:31
Bid in the amount of $25,000
Mac1955
Bid
Aug 6, 2026 · 01:36
Bid in the amount of $22,001
Aug 5, 2026 · 21:30
1939 Cadillacs did not have turn signals when new.
Aug 3, 2026 · 19:15
@Seller: Thank you for tagging "@Dollycat3 and me" :)
Your 99th auction is a fabulous statement.
Anywhere one goes in this gem ...they've "arrived" ....in more ways than one.
I look forward to your 100th. Continued success.
Your 99th auction is a fabulous statement.
Anywhere one goes in this gem ...they've "arrived" ....in more ways than one.
I look forward to your 100th. Continued success.
Aug 1, 2026 · 20:32
This one may be of interest: @rhodium45 @grantslogan1 @TShiery
Another beauty for @Dollycat3 and @Hoppy18 to enjoy!
Another beauty for @Dollycat3 and @Hoppy18 to enjoy!
1931Bentley
Bid
Aug 1, 2026 · 19:25
Bid in the amount of $20,000
Aug 1, 2026 · 15:41
I believe that car was on the CCCA car tour that went from Newport Rhode Island to the San Francisco Bay Bridge about 25 years ago. Still looks lovely.
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Just something for the next owner to think about.