How do I talk to this boy?

I've had a crush on this guy who lives in my dorm since September, but I haven't known how to approach him or speak to him to get him interested in me. I'm finally ready to go talk to him and take that step, but I don't know how to just start talking to him out of the blue like this. 
I am also transferring schools next year, and he is not, but I recently found out that he lives near me at home. Is this something I should even bother pursuing, and if so how should I go about it?
Any advice you can give I'd be most grateful for!