You might want to check out VideoLAN, Icecast(which sould work pretty well with Winamp), or StreamStudio. VideoLAN should be available for whatever OS you are using, I'm not sure about the others. Icecast is commonly used for winamp apps. All of the above should work and are free, open source programs.
Also, It does seem a little silly to stream them, when you could just share a folder over your network. Just out of curiosity, why stream?
Never swing a sword with your fist in your mouth.