This might be a stretch, but if you want your code to be nice and UNIX-ish, you could possibly run an SSH server on your Windows machine. Sure, it's not the most Microsofty solution, but it would allow you to use something like Net::SSH and then Migration away from Windoze would be easier :)

Using the Windows telnet daemon is doable, but you will be sending plaintext passwords...avoid telnet!

Other options might be to write a daemon process for the other machine, using something like XML::RPC or some other RPC module. Whatever you do, don't forget encryption and authentication!