The 1964 work is guided at £300,000-500,000 at the September 26 sale taking place in the West Norwood saleroom.
Pony comes from a key period in Caulfield’s career and is being offered for sale for the first time on the open market since its original purchase directly from the artist in the year of its conception.
It was on loan to the Tate gallery in 1981 for inclusion in the artist’s first major retrospective titled 48 Paintings from 1963-81, and was also in the artist’s third retrospective exhibition in 1999 comprising 55 paintings from the years 1961-97 at The Hayward Gallery.
Apart from these public appearances the painting has remained in the same family’s possession since 1964, having been purchased by Mr and Mrs Tom Chetwynd; then by descent. The Chetwynds were friends of Caulfield and they purchased this work alongside Still Life with a Dagger (1963), now held by the Tate in London.
On initial inspection, Pony, which is painted on board in household oil-based paint and measures 4 x 5ft (1.22 x 1.53m), may appear to be a painting which can be commonly associated with the Pop Art style.
However, Roseberys director Marcus Grey said: “Where Pop Art focused on the throwaway culture of consumerism, Caulfield was looking to challenge himself and the viewer by presenting often traditional, romanticised subject matter that many other modern artists of the time shied away from.
“It could be argued the stylised line, bold colours and flattened surface areas in his works are almost the only crossover between Pop Art and his work.”