If your asking if you can build an ASIC that runs windows then no, you cannot. It takes tens of millions of dollars in fabrication and design costs to get an ASIC and you would need a team that knows what they are doing. I would look into the current manufactures and buy one to run in your house to start off.
It would be windows running the asic, not the asic running window's. There is not a chance any miner comes out that uses windows as OS. Window's has ran certain miner's and honestly it does not end well on the few that focused on window's. Only one I can think off the top of my head was a Scrypt miner the SF-28 that actually had a window's only support (at least when I owned it)... and it really did not end up well long term.
You can use windows to learn with a compac. Sidehack posted above... he actually get's a ton of credit with making these usb stick miner's. With it you can learn a lot with cgminer and actually using commands. It is a fun project BUT before going window's route on it I would invest in a raspberry PI. There are great tutorial's and you can run it on a low cost controller this way vs a full windows machine.
But in all honestly to OP most miner's at this point are pretty GUI. Look at any recent decent sized miner you will see you don't really design anything... it's already done and you really just put in your pool info. If your wanting to "build" an asic is not really for you possibly a Ether machine with GPU's if you really have the bug to build.... but that get's into a whole different topic.
