Norman Rockwell's Which One? (Undecided Man in Voting Booth) will headline Sotheby's November 21 American Art sale in New York.
The work dates to 1944. Like many of Rockwell's most famous paintings, it served as the cover of an edition of the Saturday Evening Post.
'Which One?' is being sold for the first time since the 1980s
At the time the nation was gripped by the tightly run race between Franklin D Roosevelt and the Republican candidate Thomas E Dewey.
While this year's US election will have long since been decided by the date of the sale, the work is sure to attract strong bids.
It's valued at $4m-6m.
Rockwell's price point has escalated dramatically in recent years, most notably with the sale of his masterpiece Saying Grace in 2013.
That painting realised $46m, setting an artist record that stands to this day.
Alfred Bierstadt's Yosemite (circa 1875) is expected to reach $1.5m-2.5m.
Bierstadt was among the first painters to capture the stunning Yosemite Valley region. He travelled there with the various wagon trains carrying people west to begin new lives.
His work was very popular with collectors during his own lifetime.
This canvas is believed to have belonged to Union army general and US president Ulysses S Grant.
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