A portrait of the roguish 2nd earl of Essex, Robert Devereux, painted by Isaac Oliver (1565-1617), will highlight an auction of the collection of Valerie Eliot next month.
The wife of the poet TS Eliot's collection will sell at Christie's London on November 20.
Oliver was a painter of miniatures, who moved to England from France to escape the wars of religion.
He studied his art under Nicolas Hilliard, and became a painter in the court of James I following the death of Elizabeth I in 1603.
The painting is expected to make £300,000-500,000 ($484,800-808,000).
John Constable's Helmingham Dell, Suffolk (1800) will also feature in the sale, valued at £250,000-300,000 ($404,000-565,600).
Recent times have seen a number of high profile sales of Constable's work, with a "lost" sketch of Coleorton Hall achieving £67,250 ($101,500) at Bonhams London earlier this year, while Salisbury Cathedral from the Meadows sold privately for £23.1m ($34.7m) in May.
The auction record for a Constable is held by The Lock, which sold for £22.4m ($35.2m) last year.
Orlando Rock, deputy chairman of Christie's Europe, commented: "Christie's is delighted to be entrusted with the collection of the late Mrs TS Eliot.
"Valerie's devotion to her husband helped her form a particularly enlightened collection of British art which she knew he would have applauded and cherished.
"Compiled over 20 years, the collection encapsulates the history of British art from Hilliard to Freud via Gainsborough, Spencer, Moore and Bacon; and includes quintessentially English sea and landscapes by Constable, Turner, Atkinson Grimshaw and Lowry."
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