Botticelli’s 15th-century portrait of a nobleman in Young Man Holding a Roundel is the highlight of Sotheby’s Masters Week sale series in New York in January.
Opportunities to acquire a Botticelli – the artist behind such masterpieces as Primavera and The Birth of Venus – are very rare.
Christopher Apostle, who has for more than three decades handled Old Masters and is now head of the division, said: “Just the sheer beauty of this has been a joy.
“I can’t think of a Botticelli like this that’s been on the open international market.
“The fact that there are 12 known portraits by Botticelli puts it in an elite type of situation.
“These are the most personal things he produced, in a way. It’s just something he’s doing with one individual.”
The auction house believes it could sell for more than 100 million dollars (£77.8 million).
The last painting to achieve that level at auction was Claude Monet’s Meules at Sotheby’s New York in 2019, going for 110 million dollars (£85.6 million).
If it reaches those dizzying heights, it would represent a windfall for the present owner.
The painting was last acquired at auction in 1982 for £810,000.
We've seen even during this time period that people are hungry for art, hungry for masterpieces, always
Mr Apostle does not believe the global pandemic will depress interest in the work.
He said: “We’ve seen even during this time period that people are hungry for art, hungry for masterpieces, always.”
The painting – believed to have been executed in the late 1470s or early 1480s – actually represents two artworks.
Botticelli painted the noble sitter but the roundel – a circular disc used as a symbol – depicts a saint and is an original 14th-century work attributed to the Sienese painter Bartolomeo Bulgarini.
Who the young man depicted has been lost to history, as well as why he holds the roundel.
Some scholars believe he is associated with the ruling House of Medici or another powerful family in Florence.
Mr Apostle said some things can be inferred.
The young man’s hair is long and fashionable for the time, while his tunic is buttoned up and restrained, dressed in a republican way.
“There’s a rectitude to this picture and a lack of arrogance while still being very confident that I think exemplifies that attitude that these republicans in Florence felt about themselves,” he said.
“Also, by presenting this medallion, he’s just making sure we’re aware he’s a cultivated person.”
In the past 50 years, the painting has spent extended periods on loan at the National Gallery in London, the Metropolitan Museum of Art in New York and the National Gallery of Art in Washington.