You might want to look at a Tartan 30. Designed by famed Sparkman & Stephens, built in the late 60s and 70s, sails well, relatively comfortable to live on (get an oven) ... headroom, hmmmmm. I''d nearly 6''0" and I was OK, I think the "official" headroom is 6''3" but that is not throughout the cabin. Well built for a production boat. Some take them on ocean passages (not enough tankage in my opinion, though. Easy to singlehand!
Our 2nd boat was a T30. We still miss her sweet lines and performance!!!
Have you yet discovered www.yachtworld.com and boats.com?
Good luck and have fun!