Gerhard Richter's Dusenjager (1963) will headline Phillips' 20th Century & Contemporary Art evening sale in New York on November 16.
It's expected to make around $25m-35m.
The piece is an early example of Richter's photorealistic paintings, which he was inspired to create after his exposure to pop art.
It's one of eight depicting warplanes.
The name translates as "dusk hunter".
It's a hugely dynamic representation of the tensions that existed in Germany (and the rest of the world) in the post-war era.
The work last sold for $11.2m in 2007, indicating the growing market for Richter's work.
Jean-Paul Engelen, co-head of 20th century & contemporary art at Phillips, comments: "We're honored to include Dusenjager from Gerhard Richter's series of warplanes in our sale, which is easily the most important work by the artist to have ever been offered by Phillips.
"His photorealist paintings, especially those of such high quality, are rare to the market and the auction on November 16th presents an exceptional opportunity for collectors and institutions to acquire such an iconic work."
Other examples of Richter's photorealistic works have achieved phenomenal sums in the past, with his Domplatz, Mailand selling for the then record price of $37m in 2013.
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