A 1955 Mercedes-Benz 300 SL 'Gullwing' is to star in RM Sotheby's Driven by Disruption sale in New York on December 10.
It's expected to make $5m-7m, which would make it the most valuable example of the model ever sold.
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The car has a strong racing history, having been driven by Stirling Moss to second place in the 1956 Tour de France.
It was one of four racing specimens built in 1955 and features a variety of upgrades not included with the production model.
Alain Squindo, vice president of RM Sotheby's, comments: "This car illustrates an important and lesser-known chapter in the Gullwing racing legend.
"Not only is it rarer than the ever desirable alloy-bodied Gullwings, but its desirability is amplified by its astonishing provenance - none other than Sir Stirling Moss drove the car to a second place finish at the '56 Tour de France, beaten only by de Portago in his Ferrari, which RM sold for a world record $13.2 million in Monterey earlier this year.
"It begs the consideration of any serious collector in search of the ultimate Gullwing for their stable."
The 300 SL Gullwing remains one of the most sought after cars in the world. One specimen made a record $4.6m in Scottsdale in 2012 - a figure the present lot could easily surpass.
The sale will feature a wealth of important cars, including Janis Joplin's psychedelic Porsche and a 1956 Ferrari 290 MM.
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