For salaries: that depends so muc on your job and training and experience, that it is really impossible to give anything specific without knowing more. But, in order to be comfortable in this area, without children, I'd generally want at least $50k. On that salary, buying a house is more or less out of the picture, but you can rent in that price range comfortably. For something more specific and probably more helpful, let us know what type of job you have and would have if you moved here.
I really don't know anything about Winchester, except that it is a fairly decent commute into Boston. It is in a good area.
If you are looking to rent a home rather than an apartment, look in the yellow pages online to find some realtors; calling a local realtor will probably be the best bet for rental houses. You can also check out
http://www.townonline.com/winchester for more info on the town and to look for local realtors.