If you like nice, older neighborhoods, the city core has really improved in the last decade. Thornton Park, College Park, Colonialtown and Lake Eola Heights all have some very nice properties with yards and mature, tree-lined streets. If you head north a little bit more, the western portion of Winter Park (near Rollins College) is fantastic, and a few good deals can still be had. Or you could spend a bloody fortune for a Winter Park mansion. Depends on your means.

I'll also second what FlyingDog said--the market in many parts of Orlando is teetering on free-fall due to all the people who overextended themselves with "investment properties" before the subprime bubble burst. Now or the near future should be a good time to be a buyer in central Florida.

On the other hand, if you're looking to buy into a new development, be sure to do your homework on the associated companies. There have been some minor scandals with sub-par construction and corporate legal shields lately.