Whether because of history, rarity, or motorsport lineage, the most expensive cars sold at auctions are a perfect example of how the success of a specific car can make it among the sought after vehicles of all time – even several decades after it was built.
The names in this list include Ferrari, Aston Martin, Bugatti, Alfa Romeo, Mercedes-Benz, and Jaguar, with history that dates back to as early as the 1930s. The importance of these cars in the automotive world is insurmountable, and we figured it would take some time before a new one can replace any of these names.
While even the cheapest in the group is enough for you to maybe buy an entire state, you’ll know why these cars are priced that way. We’ve also included the price of the automobiles due to inflation, just to set things straight.
Go ahead, take this trip back to the memory lane of expensive automotive history.
1931 Bugatti Type 41 Royale Kellner Coupe
Price: £15,345,000 [$20,376,595]
Also known as Royale, the Bugatti Type 41 is one of the largest cars in the world, measuring 169.3 inches in wheelbase and 252 inches in overall length. It’s also powered by one of the biggest engines ever made – a 12.7-liter V8 that’s 4.6 feet long and 3.6 feet high. It was manufactured by Bugatti from 1927 to 1933.
1939 Alfa Romeo 8C 2900B Lungo Spider
Price: £15,898,575 [$21,111,686]
Another model from the 1930s, the Alfa Romeo 8C 2900B Lungo Spider is among the few sports car choices of that era. It was also the most advanced, modern, and compelling sports car that money could buy at that time, not to mention the rarest as well. Only 32 of these cars in 2.9 chassis were made, seven of which are Touring Spiders in long chassis.
1964 Ferrari 275 GTB/C Speciale
Price: £17,236,617 [$22,888,469]
This is one of the three production lightweight 275 GTB/C Speciale ever made by Ferrari, even rarer than the 250 GTO. It was designed by Pininfarina, while the bodywork was done by Scaglietti. This particular model is powered by a 320-hp V12 engine with six Weber 38 DCN carburetors and connected to a five-speed manual transaxle transmission.
1955 Jaguar D-Type XKD 501
Price: £17,488,380 [$23,222,785]
The Jaguar D-Type is title-holder of the 24 Hours of Le Mans, hailed as the overall winner of the race in 1956. This particular car, chassis number XKD 501, was sold to the Scottish racing team Ecurie Ecosse, making it the first D-Type production model who entered the race with a private team. It’s also the only Le Mans-winning C- or D-Type that has remained essentially original to its winning form.
1956 Aston Martin DBR1/1
Price: £18,214,976 [$24,187,630]
There were only five DBR1s ever made by Aston Martin, and this is the first of them. Aside from its rarity, it also has a winning bloodline, with this particular car winning the 1959 Nürburgring 1,000 km. Several known motorsport figures had a chance to race in this car, including Roy Salvadori, Stirling Moss, Jack Brabham, and Carroll Shelby, among others. Better yet, this car is maintained by Aston Martin specialists R.S. Williams.
1967 Ferrari 275 GTB/4 S N.A.R.T Spyder
Price: £19,712,560 [$26,176,269]
The 275 GTB/4 S N.A.R.T. Spyder is an ultra-rare Ferrari, with only 10 of which have ever existed. These 10 cars were only available from Luigi Chinetti who owns the North American Racing Team. He ordered 25 Spyder versions of the 275 GTB from Sergio Scaglietti and Enzo Ferrari, but due to low sales volume, only 10 rolled out.
Before being sold at the auction, this chassis number 10709 was owned by Eddie Smith of North Carolina, who had the car for 45 years, driven at a regular basis.
1956 Ferrari 290 MM
Price: £19,867,225 [$26,381,648]
The 1956 Ferrari 290 MM, specifically chassis number 0626, had a very rich racing history through the hands of the legendary James Manuel Fangio, who dominated the first decade of Formula One racing. This car entered the 1956 Mille Miglia with Fangio behind the wheel, starting last against 365 other racers. To make things worse, Fangio was driving solo through Italy’s torrential rains, which made the topless car a huge disadvantage. Nevertheless, he finished fourth overall against all odds.
That was just the start of the Ferrari 290 MM’s long history, while the car itself benefited from an engine rebuild and regular maintenance before it was sold in 2015.
1954 Mercedes-Benz W196
Price: £21,953,680 [$29,152,248]
Another motorsport veteran and a car driven by Juan Manuel Fangio, the 1954 Mercedes-Benz W196 single-seater Formula One race car went through the hands of Hans Herrmann and Karl Kling, and won the German and Swiss Grand Prix the same year with Fangio behind the wheel. It was the Grand Prix comeback of Mercedes since 1939, which was a nightmare for Maserati and Ferrari.
1962 Ferrari 250 GTO 3851GT
Price: £24,892,112 [$33,054,186]
The 1962 250 GTO is one of the last front-engined cars to remain competitive at the epitome of sports car racing. Ferrari specifically made this car to compete in GT Racing to rival the Shelby Cobra, Jaguar E-Type, and Aston Martin DP214. Only 33 true 250 GTOs were made, powered by a 296-hp 3.0-liter V12 engine. With its simplified lightweight interior, this car has braved through several FIA races, including the World Sportscar Championship from 1962 to 1964.
1957 Ferrari 335 S
Price: £25,935,000 [$34,439,035]
The history of the most expensive car in this list dates back to 1957 when the first out of four 335 S rolled out of production. The Ferrari with chassis number 0674 had its share of great drivers at its cockpit, including Peter Collins and Maurice Trintignant, who both piloted the car in sixth place in the 12 Hours of Sebring of the same year that the car was produced. Then, it finished second at the dreaded the Mille Miglia in the hands of Wolfgang von Trips. It was then upgraded to a 4.1-liter and set the lap record at the 24 Hours of Le Mans, finished fourth in the Swedish GP, and second in the Venezuelan GP. It finally won the 1958 Cuban Grand Prix with Stirling Moss behind the wheel.
With a lot of wins under its belt, partnered with rarity and history, the Ferrari 335 S deserved its price when it was sold in 2016.
