Você pode usar o Winamp SHOUTcast DSP, por exemplo, para transmitir o que estiver sendo reproduzido no seu Winamp pela LAN.
Use Winamp media player along with the SHOUTcast DSP plug-in to program and manage your SHOUTcast station in real-time. This plug-in will broadcast whatever is playing in your Winamp playlist in real time. Use Winamp's industry-leading playlist tools to manage your SHOUTcast station.