I think it's interesting that I've been in Winchester a handful of times, and never really went downtown. It's a very lively downtown area, with tons of active businesses and some really interesting architecture. Most of the buildings seem pretty well preserved, and a couple were undergoing some extensive renovations. I was really impressed by not only how big downtown Winchester is, but by how busy it was.
Not to mention that the drive from Lexington to Winchester is among the prettiest I've been on yet. It's like something out of a horse country theme park - if such a park were to exist.
Anyway, this courthouse building is massive. The oldest part of it was completed in 1855, costing $40,000. The clock tower was put in in 1889, and the back part of it that you can't see in this picture was built in 1938. The coolest part about the addition though, is that it perfectly matches the and mirrors the front you see here. Based on some of the other courthouse expansions I've seen, this one is pretty stellar.
BONUS PIC FOR PETER - This appears to be a courthouse annex or "judicial center" in Clark County. I thought Peter would like this one, because it's not your typical annex. This building was built by the Federal Government in 1912 and was used as a post office for almost 90 years.