Montague Dawson's Two Clippers - Nocturne is among the stars of an estate sale at Doyle New York.
The work originates from the collection of Nelson Doubleday Jr (1933-2015), former head of Doubleday publishing.
Dawson (1890-1973) was an acclaimed British maritime artist who specialised in painting historical sailing ships.
He also served with the Royal Navy during the second world war and produced a series of celebrated illustrations depicting the surrender of the German high fleet.
The present work shows his extraordinary eye for detail and drama.
It's expected to make around $150,000-300,000.
A leaf from the Gutenberg Bible (1450-1455) is also featured, with an estimate of $40,000-60,000.
This edition of the Bible was the first produced using movable type and kicked off a printing revolution that led to an increase in literacy and political awareness across Europe.
Antiquarian Gabriel Wells acquired a complete copy of the book in the 1920s. It was in less than perfect condition so he decided to split it into individual leaves, which were rebound with an essay by collector A Edward Newton.
Doubleday was a lifelong New York Mets fan and at one time owned a 50% stake in the team.
The sale will include a ring awarded to members of the team and staff in the 2000 National League Championship.
It's expected to make around $8,000-12,000.