A 1918 24c Inverted Jenny stamp is valued at around $350,000.
The lot is part of the legendary collection of the late Irwin Weinberg, which will sell at Robert A Siegel in New York on November 9.
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The Inverted Jenny is the most famous error stamp in US philately, one of very few known to people outside the hobby.
Only 100 exist and all originate from a single sheet bought by collector William T Robey from a post office in Washington, DC.
This stamp is from position 100, meaning it's the final stamp on the bottom right of the sheet.
After being pressured by government agents he sold the sheet on to a dealer, who split it up into singles and blocks of four.
One single sold for a record $1.3m at Siegel in May of this year.
Weinberg was a giant in the philatelic world and some of the greatest US stamps of all time have passed through his collection.
This Inverted Jenny was one of four he owned.
Weinberg also famously bought the 1c magenta British Guiana for a record $220,000 in 1970 - a fraction of the $9.5m it sold for in 2014.
Other highlights of the auction include an 1869 15c pictorial invert, which carries an estimate of around $22,000.
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