Russian defence ministry video showed the first group of aircraft taking off from Hmeimim air base in Syria on Tuesday morning and later in flight.
Western officials cautiously welcomed the move, saying it could pressure Syria's government to engage in talks.
Peace talks aimed at resolving the conflict are entering a second day.
UN Special Envoy Staffan de Mistura, who is mediating in the talks, welcomed the Russian decision.
"The announcement by President Putin on the very day of the beginning of this round of Intra-Syrian Talks in Geneva is a significant development, which we hope will have a positive impact on the progress of the negotiations," he said.
The Russian force reduction was announced during a meeting between Mr Putin and his defence and foreign ministers.
Russia is a key ally of Syrian President Bashar al-Assad, and his office sought to reject speculation there was a rift between the two countries, saying the move was mutually agreed.
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