Reuven Rubin's The Milkman (1928) will headline a sale of Israeli and international art at Sotheby's on December 17 with a $300,000-350,000 estimate.
Rubin (1893-1974) was an early emigre to Jerusalem, travelling from Romania to British-mandated Palestine in 1923.
He was among the first generation of Jewish artists to paint the area that would become Israel in 1948, and went on to serve as its first ambassador to Romania.
His work draws together ancient biblical and contemporary European influences, embodying the characteristics of a nation that was simultaneously brand new and ancient.
Another painting by Rubin, Mother and Child with Pomegranates (1968), is valued at $120,000-180,000.
In 2012, his Jerusalem Seen from Mt Scopus realised $542,500 at an auction at Sotheby's in New York.
Grande Baigneuse Accroupie (1925) by Chana Orloff (1888-1968) carries an estimate of $130,000-180,000.
Orloff emigrated to Israel in 1905 before leaving to study tailoring in Paris in 1910. There she discovered an aptitude for sculpture - going on to produce hundreds of examples over the course of her career.
Her auction record was set at $158,500 at Sotheby's New York in 2008 for Femme Qui Croise Les Bras (Madone) (1913).
A painting by Mordecai Ardon (1896-1992) titled Jerusalem at Night (1947) could make $120,000-180,000.
The work prefigures the highly symbolic, kabbalistic works he would go on to paint during the 1950s in its evocation of the city's night sky.
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