Arguments over the origins of Portrait of a Woman Called La Belle 3 have raged since 1920 when it was given as a wedding gift to a car salesman in Kansas City, Missouri, by a family friend who said it was by Leonardo.
Sotheby's, which is selling the painting in New York later this month, believes the painting is not by him and, unable to say exactly who did paint it, is basing its estimate of $300,000 to $500,000 partly on the portrait's notoriety.
"Leonardo is a magic name. Even if you say it's not Leonardo but close to that, people get intrigued," said George Wachter, head of Sotheby's Old Masters department.
"It's history is important to it but it's also important to understand the painting's quality is really high. I am sure some people will think it is by Leonardo - it's a very emotive picture."
The auction house says the portrait is another version of a composition in the Louvre, believed to be by Leonardo or a pupil, depicting Lucrezia Crivelli, a mistress of Ludovico Sforza, the Duke of Milan and the artist's patron.
Little is known of its provenance before the car-dealing Harry Hahn and his new French wife, Andrée Lardou, were given the painting in 1920 by her godmother, Louise Montaut, under the assumption it was by Leonardo. Sotheby's believes it may have been looted from the royal French collection during the revolution.
Soon after, the couple were about to sell the painting to the Kansas City Art Institute for the hefty sum of $250,000 - nearly $2.7 million today - when a reporter phoned the famous British art dealer Lord Duveen to ask him to comment. Woken in the middle of the night, he immediately pronounced the portrait a fake.
Mrs Hahn sued him for $500,000 for slander and damages, and, after eight years and a first trial which returned an open verdict, the highly publicised case went to the New York Supreme Court.
Both sides produced their own experts and Lord Duveen told the court the painting was not by Leonardo and - more damningly - was merely a later copy.
The jury was hung but a majority sided with the Hahns. Before a retrial could begin, Lord Duveen paid $60,000 in an out-of-court settlement.
Although the portrait was never sold despite several attempts, the discussion continued about its authorship.
In 1993, a Leonardo expert analysed the picture and decided it was not by the artist but dated to the first half of the 17th century, which was supported by tests on the paint last year.
Sotheby's, which sold a Mona Lisa once attributed to Leonardo for $500,000 in 1995, said it had received "a lot" of calls from people interested in the new painting.