You may have a Window's related problem, where Tk's fileevent dosn't work reliably on some version of windows. See Client/Server sockets with TK on Win32 .

There are workarounds, see Another Win32 Tk fileevent work around : using ioctl() properly for instance. If that dosn't work for you, it's possible to use a conventional select loop with sysread in a separate subroutine, and call it with a Tk timer every 10 milliseconds. See Tk fileevent with win32 sockets for a timer solution.

It goes something like this untested code:

... other Tk code 
my $timer = $mw->repeat(10, \&read_it );
MainLoop;

sub read_it{
   my $client = $listen->accept or die "Accept failed: $!";
   if( IO::Select->new($client)->can_read(5) ) {
      sysread( $client, $_, 1 ) and print;
   } else {   print "Timeout\n";
   } close $client;
}
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Also see Mastering Perl/Tk and the Window's fileevent problem

If you are an eager seeker of Perl knowledge, I will tell you that another, more advanced GUI toolkit, called Gtk2 does have an IO watch ( like fileevent ) which does work on Windows, see Simple threaded chat server for a simple example to test with.

Finally, you could just put Ubuntu Linux on your Desktop with a dual boot to Windows. :-)

Finally, just to get you banging your head against the wall, I found an example of Wx using sockets, see Wx Socket. It probably works on Windows.