I am NOT a real estate agent, so I have no vested interest in this answer. Coming from the Midwest in the 1980's, I checked out both Florida Coasts before I settled on the Gulf Coast side.
The Atlantic side is much too busy and rush-rush for me. Yes, the weather is about 5 degrees warmer than the Gulf side, but it is prone to more hurricane danger and, because of the congestion, much more prone to crime. If you like the hustle and bustle of a big city like New York, then the east coast side is it. If you like more of a midwestern attitude, go to the west side of Florida.
Florida real estate values are down across the board and you might get a better deal on the Atlantic side, but there are plenty of deals on the Gulf side too. For my tastes, the Atlantic side is too congested. I would prefer the west coast from about Citrus/Hernando down to Sarasota. The northern counties actually get cold in the winter with a more distinct winter season. Go south of Tampa/St. Pete to blunt that winter effect. By going to the Naples/Fort Myers area, you pretty much avoid cold winter weather - but you run up against much higher prices and into the "relocated refugee's from the east coast" (those who lived on the Atlantic side and found out the hard way they didn't like it.).
A little background on me, I lived in Tampa (felt too northern for me!), moved to St. Pete and still live on the water - but the insurance premiums have gotten to me. I own a small parcel of land in eastern Manatee county (the REAL boondocks complete with wild boar, turkey, deer, snakes, gators!!!) and am looking forward to moving toward Panther Ridge or Lakewood Ranch in Manatee County soon due to family reasons. There are reasonable deals all over the place, I expect to snag one myself. - Thu May 15 2008, 03:38