A synchronization apparatus and method for synchronizing playback time of a media provided to multiple devices during service transfer and replication process are provided. The content synchronization system for providing a receiving terminal with content of a sending terminal, the content synchronization system includes the sending terminal; the receiving terminal; and a server configured to provide content to the sending terminal and the receiving terminal and to comprise a communication unit configured to communicate the sending terminal and the receiving terminal and to transmit a message and information about time point at which the message is sent, and a content playback time point calculating unit configured to calculate a first content playback start time point of the receiving terminal in an effort to provide the content of the sending terminal that is synchronized with the receiving terminal.