The Most Expensive Car Sales in Auction History

In this edition of Under the Hood, we’ll be diving into the wild side of expensive car collecting. This is where cars stop being just machines and start being works of art, history, and obsession. Prices here don’t just climb – they explode. Take 2022, for example. A 1955 Mercedes-Benz 300 SLR Uhlenhaut Coupe sold for $142 million. Not at Monterey, not in the middle of the usual auction frenzy, but quietly in Stuttgart. The hammer dropped, and the entire collector world gasped. Even the veterans didn’t see that coming. Sales like that don’t happen because someone thought, “Hey, nice paint job.” They happen because of four things: rarity, history on the track, famous owners, and condition, so perfect it feels unreal.

Whether you’re chasing Ferraris in Monterey or browsing classics online, those same rules apply – the only difference is the size of the check. Here are the 20 sales of the most expensive cars that changed everything.

20. 1935 Duesenberg SSJ – $22 Million

Only two of these exist. Hollywood icons Gary Cooper and Clark Gable got them both. Cooper’s SSJ hit Pebble Beach in 2018 and set the record for the most expensive American car ever auctioned. In 1935, it could hit 140 mph: supercharged, twin-carb, pure American ambition.

19. 1956 Ferrari 290 MM – $22 Million

This Ferrari carried Juan Manuel Fangio’s name. He drove it in the Mille Miglia. When a five-time world champion leaves his mark on a car, the price tag follows.

18. 1955 Ferrari 410 Sport Spider – $22 Million

Before Carroll Shelby became “Carroll Shelby,” he was behind the wheel of this Ferrari. He won eight races in it. Only two were built with the monster 4.9-liter, 24-spark-plug V12, explaining why this extremely rare ride was sold for a whopping $22 million.

17. 1964 Ferrari 275 GTB/C Speciale – $26.4 Million

Ferrari made just three. With that alone, it’s unsurprising that collectors would show interest. Add racing heritage, and you’ve got a car destined for the stratosphere.

16. 1967 Ferrari 275 GTB/4 S N.A.R.T. Spider – $27.5 Million

Steve McQueen once owned this one. Enough said. Pair that with its North American Racing Team story, and in 2013, it sold for $27.5 million.

15. 1954 Mercedes-Benz W196 – $28.05 Million

Before the Uhlenhaut Coupe smashed records, this F1 car was the star of Mercedes’ history. Fangio drove it to Grand Prix wins. For years, it held the title as Mercedes’ most valuable machine.

14. 1957 Ferrari 335 Sport Scaglietti – $35.8 Million

Sold in Paris in 2016, this car was Ferrari in its prime. It raced the Mille Miglia, wore stunning Scaglietti bodywork, and ticked every box a collector could dream of.

13. 1962 Ferrari 250 GT SWB California Spider – $36.2 Million

California Spiders are always hot property. This one stood out with flawless documentation and condition, the kind that takes an expensive car from “beautiful” to “investment-grade.”

12. 1962 Ferrari 250 GTO – $38.115 Million

In 2014, Bonhams sold this GTO for over $38 million. At the time, that felt like the absolute ceiling. Nobody thought prices could go higher. They were wrong.

11. 1962 Ferrari 250 GTO – $48.4 Million

Four years later, RM Sotheby’s smashed that record. This GTO sold for $48.4 million in 2018 and officially became the car everyone measured against.

10. 1962 Ferrari 330 LM/250 GTO – $51.7 Million

This one’s special. It started life as a 330 LM before Ferrari converted it to GTO spec. That made it unique in an already exclusive group. In 2023, it became the priciest Ferrari ever sold publicly.

9. 1963 Ferrari 250 GTO (Private Sale) – $70 Million

Not all the biggest deals happen under the lights. This one was done quietly in 2018. A GTO changed hands for $70 million—proof that the most serious collectors don’t always need an audience.

8. 1955 Mercedes-Benz 300 SLR Uhlenhaut Coupe (Private Sale) – $70 Million

The second Uhlenhaut Coupe was sold privately too, for the same eye-watering figure. No cameras, no drama—just a collector paying what it took to own one of the rarest cars on Earth.

7. 1994 McLaren F1 LM-Specification – $19.8 Million (2019)

Finally, a modern supercar broke into the mix. The LM-Spec F1 was about as close as you could get to a road-legal race car. Collectors loved it, and the price proved it.

6. 1995 McLaren F1 – $20.5 Million (2021)

This one had barely been touched – just 243 miles on the odometer. It was essentially brand new, and in 2021, that level of preservation proved more valuable than restoration.

5–3. Various High-Value Ferraris – $22–35 Million Range

Ferraris rule this space. 290 MMs, 375-Plus models, one-offs—each dripping with racing history and exclusivity. They’ve earned their eight-figure homes.

2. 1963 Ferrari 250 GTO (Private Sale) – $80+ Million

Industry whispers say at least one GTO has changed hands for more than $80 million. The exact number? A mystery. But in this world, rumors usually carry truth.

1. 1955 Mercedes-Benz 300 SLR Uhlenhaut Coupe – $142 Million

The big one. Mercedes decided to part with one of its two museum-held Uhlenhaut Coupes. Rudolf Uhlenhaut’s masterpiece of engineering went under the hammer and rewrote history. The fact that proceeds went to charity made it more than just a sale – it was a moment.

What This Means for Everyday Collectors

Why should these insane sales matter to anyone outside the billionaire circle? Because they set the tone for the whole market. The factors that push a car to $142 million: rarity, history, condition, and proof of authenticity, apply at every level. Here’s the truth: you don’t need $20 million to play the game. What you do need is research, patience, and an eye for detail. Collectors with modest budgets find overlooked gems all the time. It’s about knowing the story behind the car and spotting value when others miss it. Whether you’re waving a paddle at Pebble Beach or scrolling an online auction late at night, the rules don’t change. Buy what you love. Know what you’re buying. And never assume the most expensive car is the best car in the room.