His 1932 book Painting as a Pastime detailed his love of this hobby and now a small collection of photos has emerged at auction showing him at his easel before the outbreak of the First World War.
The photos, taken at Hartsbourne Manor in Hertfordshire, will be offered at auction in Bristol later this week.
Consigned by a local vendor, the collection of photos date from 1913. East Bristol auctioneer Andrew Stowe said: “It’s an incredible sight. Here is one of Britain’s most famous historical figures – relaxing, and enjoying his time with his friends and family. Meanwhile, the world is just months away from absolute turmoil.”
The images show Churchill, his wife Clementine and his friend Maxine Elliott relaxing in Elliott’s Hertfordshire country estate, Hartsbourne Manor near Bushey Heath.
In two of the images, Churchill can be seen finishing off a painting at Elliott’s home.
The American actress and famous socialite was a friend of Churchill and was also rumoured to have had an affair with King Edward VII.
The photos were taken by New Zealand international tennis player Francis Fisher. Fisher is thought to have become friends with Elliott via her fiancé - the tennis player Tony Wilding (who was later killed in action in 1915).
One image depicts Churchill wearing his artist's smock, with palette and paint brush in hand and his signature Homburg hat. To the rear of the image, in the hand of FMB Fisher, is written Winston Churchill finds a new pastime besides politics - at Hartsbourne.
Another photo shows Churchill with his back to the camera painting. His wife stands beside him, looking at the photographer. The margin is annotated Mr & Mrs Winston Churchill at Hartsbourne Manor and, also in the hand of Fisher, to the verso is written: Mrs Winston Churchill + her husband.
A third photo shows Elliott with Lady Diana Manners. In Fisher’s hand on the reverse of the photo is Miss Maxine Elliott (with cigarette) + Lady Diana Manners - on the red court at Hartsbourne.
The collection comprises three photos, a letter and a ticket and will be offered at East Bristol Auctions’ specialist Military, History & Transport Auction on May 18, with an estimate of £300-500.