Sherwood was born in Moscow. He was of English descent, his grandfather Joseph Sherwood having been an English engineer who emigrated to Russia. His father was the architect Vladimir Osipovich Sherwood and his brother was the architect Vladimir Vladimirovich Sherwood.

Leonid Sherwood was responsible for the Makarov Monument [ru], a memorial to Admiral Stepan Makarov, killed during the Russo-Japanese war. It was erected in 1913 on Anchor Square in front of the St. Nicholas Naval Cathedral in Kronstadt. Sherwood chose to use as the pedestal a 160-ton granite rock originally cut for a monument to Paul I in front of Kazan Cathedral, which sank in transit to Saint Petersburg. The base of the rock is engraved with the words: "Remember the War".

Sherwood was one of the first sculptors to be involved in monumental Soviet sculpture after the revolution and was responsible for many official busts and monumental statues. He was also the architect of the Swallow's Nest, a decorative castle in the Crimea.

Sherwood was educated at the Moscow School of Painting, Sculpture and Architecture (1886–91) and the Imperial Academy of Arts, St Petersburg (1892–1898). He was a pupil of Vladimir Aleksandrovich Beklemishev. He was an exchange student in Paris in 1899–1900, where he became a pupil of Rodin. Returning to Russia, he lived in Petrograd and was employed by Vladimir Lenin for monumental sculpture. He taught sculpture at the Academy of Arts in Petrograd. Among his pupils was Sarra Lebedeva.^[1]

Sherwood was awarded the Order of the Red Banner of Labour and was made a Distinguished Artist of the RSFSR. He died in Leningrad, aged 83.