Irma Stern's Swazi Youth will lead a sale of South African art at Bonhams London on March 16.
It's expected to make around £200,000-300,000 ($286,793-430,189).
Following a period spent studying art at the Weimer Academy in Germany during the 1910s, Stern returned to Africa.
In the 1920s and 1930s she embarked on a series of lengthy travels through the continent. The present work dates from this period.
Bonhams comments: "In many ways, Swazi Youth is a romanticised depiction of man in a state of nature.
"The youth's pose, with his arms outstretched behind his head, suggests a carefree attitude, free from the constraints of urbane social conventions.
"The portrait is Expressionist in that it reveals as much about Stern's longings as it does her subject."
A similar work from this period, titled Swazi Girl, sold for £311,200 ($446,249) at Bonhams in 2008.
Another work by Stern, Still Life with Anemones (1934), carries an estimate of £180,000-220,000 ($258,113-315,472).
Stern's still life paintings are among her most sought after.
Stern's work has grown in value in recent years, with a $5m record set for a painting titled Arab Priest in 2011.
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