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
Sold on 08/17/2026 for USD $68,000 to safarilang
Bids & Comments
bobestes100 0
Aug 17, 2026 · 17:30
Like I have said before, just not as much interest in the pre war cars now. Us old guys are a dying breed & holding on to our money!
Aug 17, 2026 · 17:24
A sad comment of the interest
interest in Grand Classics.
interest in Grand Classics.
Aug 17, 2026 · 17:23
1 of 28 but more likely 1 of 1 or 2 ...
Aug 17, 2026 · 17:22
Cut a deal ...
Aug 17, 2026 · 17:22
Sad trombone…
safarilang
Bid
Aug 17, 2026 · 17:19
Bid in the amount of $68,000
brunosofbrooklyn
Bid
Aug 17, 2026 · 17:17
Bid in the amount of $66,000
safarilang
Bid
Aug 17, 2026 · 17:15
Bid in the amount of $65,000
brunosofbrooklyn
Bid
Aug 17, 2026 · 17:14
Bid in the amount of $62,000
gharzai
Bid
Aug 17, 2026 · 17:12
Bid in the amount of $61,500
Aug 17, 2026 · 17:12
Think I've lived with my Etype, 4 on the floor
Aug 17, 2026 · 17:12
The market appears to be well divided
between the age of buyer and seller.
between the age of buyer and seller.
brunosofbrooklyn
Bid
Aug 17, 2026 · 17:11
Bid in the amount of $61,000
gharzai
Bid
Aug 17, 2026 · 17:10
Bid in the amount of $60,500
Aug 17, 2026 · 17:09
You have not lived until you’ve driven a three-on-the-tree!
safarilang
Bid
Aug 17, 2026 · 17:08
Bid in the amount of $60,000
gharzai
Bid
Aug 17, 2026 · 17:08
Bid in the amount of $56,500
Bigleo
Bid
Aug 17, 2026 · 17:06
Bid in the amount of $56,000
safarilang
Bid
Aug 17, 2026 · 17:05
Bid in the amount of $55,000
Bigleo
Bid
Aug 17, 2026 · 17:05
Bid in the amount of $53,100
Aug 17, 2026 · 17:04
I own the 1938 version of this car and can say with confidence that it is one of the greatest prewar tourers I’ve ever driven. Amazing machine with presence that can’t be reviled, gets more thumbs up than just about anything else I’ve owned. Best of luck!
safarilang
Bid
Aug 17, 2026 · 17:04
Bid in the amount of $52,500
Bigleo
Bid
Aug 17, 2026 · 17:02
Bid in the amount of $52,000
safarilang
Bid
Aug 17, 2026 · 16:54
Bid in the amount of $51,500
Aug 17, 2026 · 16:53
This Cadillac is a proven tourer and frequent show car! This Cadillac was featured at Pebble Beach Concours after restoration in 1994. It has been extensively toured across Europe and North America! The Gear vendor overdrive is a plus that makes this Cadillac ready for long distance. Truly a gem and one to add to an active collection! Down to the final minutes, don't miss out!
Tasmaniandevil
Bid
Aug 17, 2026 · 16:41
Bid in the amount of $51,000
Aug 17, 2026 · 16:29
She’s absolutely stunning.
GLWTA!
GLWTA!
Dwhelmer
Bid
Aug 17, 2026 · 16:15
Bid in the amount of $50,000
Aug 17, 2026 · 16:15
I was the happy owner of a 1940 Caddy Opera Coupe for many years. I used to drive it everywhere. No problems whatsoever. I can’t believe how low the bidding is on this car! Twenty years ago this would be a $125 to $150,000 car. The new younger buyer demographic in car collecting doesn’t really care about pre-war cars anymore.
Gross707
Bid
Aug 17, 2026 · 15:55
Bid in the amount of $40,000
Aug 17, 2026 · 15:48
AS the former owner of a 1937 Cadillac, I can attest that these are solid honest cars, fully comfortable in modern traffic. The overdrive is a nice bonus - mine would "go as fast as you should care to drive it", but the silky smooth V8 was spooling along rather briskly at freeway speeds.
safarilang
Bid
Aug 17, 2026 · 14:57
Bid in the amount of $37,500
Aug 17, 2026 · 14:00
Final 3 hours!
We're down to the final few hours with this remarkable 1939 Cadillac Series 75 Fleetwood Convertible Coupe.
Over the past week we've talked about the rarity, the Fleetwood coachwork, the award-winning restoration, the massive 141.3-inch chassis, and some of the wonderfully clever details that make this Cadillac so special.
But ultimately, cars like this aren't about specifications on a page. They're about the experience.
Nearly 19 feet of prewar Cadillac. Top down. That long hood stretched out in front of you. The smooth 346ci V8 pulling you down the road. And the realization that you're behind the wheel of one of just 27 originally built.
For those who have been watching from the sidelines, we're entering the part of the auction where it gets interesting.
We're here and available for any last-minute questions, photos, calls, or information anyone needs to bid with confidence.
Thank you to everyone who has followed along. Let's bring this beautiful Cadillac home!
We're down to the final few hours with this remarkable 1939 Cadillac Series 75 Fleetwood Convertible Coupe.
Over the past week we've talked about the rarity, the Fleetwood coachwork, the award-winning restoration, the massive 141.3-inch chassis, and some of the wonderfully clever details that make this Cadillac so special.
But ultimately, cars like this aren't about specifications on a page. They're about the experience.
Nearly 19 feet of prewar Cadillac. Top down. That long hood stretched out in front of you. The smooth 346ci V8 pulling you down the road. And the realization that you're behind the wheel of one of just 27 originally built.
For those who have been watching from the sidelines, we're entering the part of the auction where it gets interesting.
We're here and available for any last-minute questions, photos, calls, or information anyone needs to bid with confidence.
Thank you to everyone who has followed along. Let's bring this beautiful Cadillac home!
Tasmaniandevil
Bid
Aug 17, 2026 · 12:24
Bid in the amount of $36,000
Aug 17, 2026 · 06:56
When Cadillacs were Cadillacs!
GLWA
GLWA
Aug 17, 2026 · 04:14
Ever since I first saw one of these, I've been awed by the sheer absurdity of putting a two seat roadster on a Series 75 chassis.
So *deliciously* impractical.
(but that trunk [what is it, 12 feet deep or so?] would have held a lot of bodies here in Las Vegas back in the day, save that it was tacking to use anything but a Deville . . .)
So *deliciously* impractical.
(but that trunk [what is it, 12 feet deep or so?] would have held a lot of bodies here in Las Vegas back in the day, save that it was tacking to use anything but a Deville . . .)
safarilang
Bid
Aug 17, 2026 · 02:51
Bid in the amount of $35,000
RJ538
Bid
Aug 17, 2026 · 00:20
Bid in the amount of $32,250
safarilang
Bid
Aug 16, 2026 · 22:08
Bid in the amount of $32,000
Aug 16, 2026 · 21:40
Less than 24 hours to go!
It's fitting that as some of the world's great automobiles gather at Pebble Beach today, we're entering the final day with this remarkable piece of prewar American motoring.
Just 27 Series 75 Convertible Coupes were built for 1939, with only a handful believed to survive. Fleetwood coachwork, a 141.3-inch wheelbase, Cadillac's 346ci V8, CCCA Premier Senior honors—and nearly 19 feet of Art Deco-era presence.
We've enjoyed sharing some of the history, details, and driving experience of this Cadillac over the past week. Tomorrow, one more chapter begins when its next caretaker takes the wheel.
We'll be here through the finish to answer questions, provide additional photos or information, and help however we can.
Good luck to everyone watching and participating. Let's have some fun in the final 24 hours!
It's fitting that as some of the world's great automobiles gather at Pebble Beach today, we're entering the final day with this remarkable piece of prewar American motoring.
Just 27 Series 75 Convertible Coupes were built for 1939, with only a handful believed to survive. Fleetwood coachwork, a 141.3-inch wheelbase, Cadillac's 346ci V8, CCCA Premier Senior honors—and nearly 19 feet of Art Deco-era presence.
We've enjoyed sharing some of the history, details, and driving experience of this Cadillac over the past week. Tomorrow, one more chapter begins when its next caretaker takes the wheel.
We'll be here through the finish to answer questions, provide additional photos or information, and help however we can.
Good luck to everyone watching and participating. Let's have some fun in the final 24 hours!
RJ538
Bid
Aug 16, 2026 · 19:31
Bid in the amount of $31,250
Harrycad
Bid
Aug 16, 2026 · 19:29
Bid in the amount of $31,000
Aug 16, 2026 · 15:58
What a beautiful car, love the art deco / streamline era - I own the "poor man's version" of this car, a Series 61 Convertible Coupe (Fisher body and shorter wheelbase). Looking at all the pictures and watching the videos makes me realize that I really need to focus on getting my car out there and enjoy it - GLWTA!
Aug 16, 2026 · 15:31
Photos 33, 59, 74 & 75 appear to show both doors out of alignment.
Aug 15, 2026 · 21:15
Amazing how modern these things drive...plenty of power, good brakes and handling (radials are transformative). My 41 Fleetwood 60 Special vs my 36 Packard Senior, night and day difference...
Aug 15, 2026 · 20:06
With just a couple of days remaining, we thought we'd share three things to know about owning a prewar Cadillac like this one:
1. It's more usable than you might think.Yes, it's 87 years old—but this was serious transportation in its day. The 346ci V8 provides plenty of torque, and the enormous 141.3-inch wheelbase makes cruising surprisingly comfortable. This car's added overdrive makes it even more enjoyable when the road opens up. It's a car you can actually drive, not simply admire.
2. You become a caretaker of something genuinely rare.Cadillac built just 27 Series 75 Convertible Coupes for 1939, and only a handful are believed to survive. At some point, ownership becomes less about having another old car and more about preserving a small piece of American automotive history for whoever comes next.
3. It changes the experience of going anywhere.You don't anonymously run to breakfast in a 1939 Fleetwood Convertible. People stop. They ask questions. Kids point. Other enthusiasts want to know what it is. And with the top down, that big V8 humming along and what seems like an acre of hood stretched out in front of you, even an ordinary drive becomes an occasion.
That's ultimately what cars like this are about. You can study the rarity, awards, history and specifications—and those things certainly matter.
But eventually you have to put the top down and drive it.
Oh, and bonus tip: at just over 19' in length, it's about the same length as a full-size SUV like the Cadillac Escalade... which means this Coupe fits in most garages.
1. It's more usable than you might think.Yes, it's 87 years old—but this was serious transportation in its day. The 346ci V8 provides plenty of torque, and the enormous 141.3-inch wheelbase makes cruising surprisingly comfortable. This car's added overdrive makes it even more enjoyable when the road opens up. It's a car you can actually drive, not simply admire.
2. You become a caretaker of something genuinely rare.Cadillac built just 27 Series 75 Convertible Coupes for 1939, and only a handful are believed to survive. At some point, ownership becomes less about having another old car and more about preserving a small piece of American automotive history for whoever comes next.
3. It changes the experience of going anywhere.You don't anonymously run to breakfast in a 1939 Fleetwood Convertible. People stop. They ask questions. Kids point. Other enthusiasts want to know what it is. And with the top down, that big V8 humming along and what seems like an acre of hood stretched out in front of you, even an ordinary drive becomes an occasion.
That's ultimately what cars like this are about. You can study the rarity, awards, history and specifications—and those things certainly matter.
But eventually you have to put the top down and drive it.
Oh, and bonus tip: at just over 19' in length, it's about the same length as a full-size SUV like the Cadillac Escalade... which means this Coupe fits in most garages.
safarilang
Bid
Aug 15, 2026 · 17:01
Bid in the amount of $30,000
Aug 15, 2026 · 05:34
It’s worth noting that one of these Cadillacs competed in, and completed, the “Around the World Rally” back in 2000. I saw the competitors in that event as they stopped for lunch at Brock Yates’ Cannonball Pub in Wyoming, NY. That Caddy convertible (it was yellow IIRC) certainly seemed up to the task…
Just something for the next owner to think about.
Just something for the next owner to think about.
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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