Thomas Gainsborough's The Blue Page is expected to make $3m-4m at Sotheby's.
The painting will provide the headline lot of a sale of Old Master paintings from the collection of the late A Alfred Taubman.
Gainsborough (1727-1788) was one of the most sought after portrait artists of his generation and a founding member of the Royal Academy.
The present work was painted while he was living in Bath, where he moved in 1758. It depicts his nephew Edward Richard Gardiner.
Gainsborough's auction record is £6.5m ($9.4m) - set for his Portrait of Miss Read, Later Mrs William Villebois at Christie's in 2011.
Raphael's Profile Portrait of Valerio Belli (1517) is valued at $2m-3m.
The work is one of few portraits by Raphael (1483-1520) still in private hands. Belli was a close friend and a well-known engraver.
The piece is small, measuring just four inches across, and executed on a round piece of walnut wood.
Raphael's status as one of the most influential painters of all time ensures a buoyant market. A sketch titled Head of an Apostle sold for £29.7m ($47.9m) in 2012.
Other pieces from Taubman's collection, including Modigliani's Portrait of Paulette Jordan, sold at Sotheby's late last year.
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