Andy Warhol’s Self-Portrait, one of his final works, is going under the hammer in New York.

The Macklowe Collection is returning to auction with a further 30 works following a record-breaking 676.1 million US dollar (£496.9 million) sale in November.

It became the most valuable ever held at Sotheby’s, far exceeding the estimate for the 35 works, and the most valuable single-owner sale.

Macklowe Collection sale
Staff prepare for a viewing of artworks from the Macklowe Collection at Sotheby’s in London prior to being offered at auction in New York (Stefan Rousseau/PA)

Sotheby’s chief executive Charles Stewart said: “The November sale of 35 works from The Macklowe Collection captivated top collectors around the world and set records in the process.

“We are thrilled to present a further 30 works from this legendary collection in May, in what is sure to be another highly anticipated sale.”

The auction on May 16 will see famous artists from the November sale return, represented by works from important moments in their career.

Andy Warhol’s Self-Portrait, painted just months before his death in February 1987, hails from his final body of works, the Fright Wig series.

Macklowe Collection sale
Gallery staff in front of paintings by Gerhard Richter (Stefan Rousseau/PA)

The monumental 80-inch portrait, which shows Warhol’s face obscured by camouflage, has only been publicly exhibited once as part of the 1995 Anthony d’Offay exhibition.

Warhol’s Nine Marilyns from 1962 was sold for 47.4 million dollars (£34.8 million) in the November auction, and Self-Portrait is estimated to sell for up to 20 million dollars (£14.7 million).

German-born Gerhard Richter’s work is making another appearance at the auction, with his 1975 Seascape, which blurs the distinction between photography and painting.

Similarly, Mark Rothko’s painting Untitled from 1960, a critical moment in his career, is expected to sell for up to 50 million dollars (£36.7 million).

Macklowe Collection sale
Gallery staff prepare a painting by Sigmar Polke called The Copyist painted in 1982 from the Macklowe Collection (Stefan Rousseau/PA)

Gregoire Billault, Sotheby’s Chairman for Contemporary Art, said: “The May selection provides a true sense of the full scope and depth of The Macklowe Collection.

“With exceptional works, this edition of the sale brings into the spotlight yet more of the key creators, movements and aesthetics that have defined art over the last 80 years.”

David Galperin, Sotheby’s Head of Contemporary Art, Americas, said: “The greatest collections convey a deep understanding and appreciation of an artist’s entire life and output.

“This is a collection that speaks to this kind of critical inquiry.”

– Highlights from The Macklowe Collection can be viewed from February 22 to March 2 in London before they go on a travelling exhibition to Palm Beach, Shanghai, Taipei and Hong Kong.