These photos are marked as publicity for The Great Dictator, so they were probably taken sometime between 1938-1940.
The first real home Chaplin ever owned was built in 1922 on 6 acres of land on a hillside next door to Pickfair. The story goes that Chaplin used studio carpenters to build the house and that it eventually began to fall apart, thus its nickname “The Breakaway House.” The original address was 1103 Cove Way but due to a reassignment of addresses sometime in the 1930s, the address became 1085 Summit Drive. The grounds included a pool, in the shape of the inside of a bowler hat, and a tennis court (built in 1929).
See more photos of the inside and outside of Chaplin’s home here.