I move to the area three years ago – in Richmond (where the job is) which is just south of Lexington. It’s a beautiful area. Lexington has/had a belt of farms surrounding it. A good chunk of those recently have been bought out (horse farm land is seriously expensive) by developers and is being built with an eye towards profit rather than quality. IMHO. The growth areas are directly north towards Georgetown and south towards Richmond. Those would be the areas I would (and have) invest in.
Personally I prefer historic homes, I am a compulsive restorer. If you swing that way, you will look to the Downtown area – historic houses are hitting close to a million or to some of the outlying communities districts. Again, Versailles, Georgetown, Richmond, and even Winchester have some cool homes – some are restore-able and reasonably priced. If you want new construction, as everywhere, some builders are reputable and some are outright crooks. There is a lot of new construction going on in that middle ring of farmland. It goes high. One of the reasons the smaller communities housing prices are shooting up.
Beautiful horse farms, great outdoor activities, if you like Bourbon, you are at ground zero – you will have to travel two hours north to find a decent brewery. Cincinnati and Louisville make good day trips for the family. I have lived in a lot of towns- for a general assessment – Lexington sees itself as a southern town, its not, it is very Midwestern. Their goal is to be average and they excel at it. That said, it is not a bad place to live. Mediocre is safe. They have a fairly active arts community, nothing cutting edge. Same with the restaurants, personalities, & entertainment -- all pretty bland. Not bad, just not engaging. The two things that do stand out are Horses and UK basketball. Unfortunately for me, I don’t care about either. I guess that’s a mixed review, it is a good town and has treated me well, I wont miss it when I make my next career move.
Hope that helps, if you want any more information, ask!