A peer-to-peer (P2P proxy server and a communication method thereof are provided. In order to participate electronic apparatuses having no built-in P2P middleware in a P2P infrastructure, the P2P proxy server includes: a proxy data communication unit acquiring a reception message transmitted through the P2P infrastructure or transmitting a transmission message to the P24P infrastructure; a legacy apparatus state management unit generating a message for advertising contents stored in the legacy apparatuses and, if the reception message is a message for requesting for sharing specific contents, generating a message for sharing the specific contents; a message management unit parsing the reception message acquired through the proxy data communication unit to transmit the reception message to the legacy apparatus state management unit or inversely parsing the message generated by the legacy apparatus state management unit to generate the transmission message and transmitting the transmission message to the proxy data communication unit; and a legacy apparatus driver connecting to the legacy apparatuses and supporting data communication between the legacy apparatuses and the legacy apparatus state management unit. Accordingly, a legacy apparatus having no built-in P2P middleware can be used as a contents source providing apparatus in the P2P infrastructure.