A software based system for facilitating streaming of media files to a device over a wide area network (WAN) includes an agent process, an authentication process, a client services process and a client process. The agent process catalogs local media files and advises the authentication process of its availability on the WAN and the address at which it may be contacted. The client process contacts the client services process to obtain, after authenticating with it, the WAN address of the agent process and contacts the agent process to receive information or meta-data describing the media files available for streaming. The client process obtains information for forming a URI or playlist, that it then passes to a media player to request the stream over the WAN. Alternately, the client process may direct the agent process to pass the URL to another client process on, for example, the same local area network.