I'm not sure how much help I'll be, but I lived in Winchester for several years (about '95-'99). We seemed to get, at most, one good/bad (depending on your point of view) snow or icestorm a year. But only once in my time there was the area so snowed in that traffic ground to a halt, and that was only several inches. I walked to and from my job, which was just shy of a mile from home, and was never bothered by any winter weather.

The summers here and there, in Winchester, are plenty hot and humid.

It is a pretty place, with lots of places to hike and DC is a short drive away. Unfortunately, everything is a short drive from Winchester, which was sometimes a bother.