OP - from your name I'm guessing you live in the Northeast. As someone who now lives in FL but is from NY, it is very different down here. I live in the Tampa area so I don't know much about Orlando beyond the tourist stuff. I would take a few long vacations (if possible), stay in rental homes/air bnb/etc. and explore the area to experience it as someone who lives there not like a tourist. Do as much research as possible before making the decision to move. If you are only looking to move down here to be closer to WDW, you might be unpleasantly surprised about the reality of living down here.
When and if you decide to move, I would recommend renting before buying a place so you can take your time to determine which neighborhood, community, etc. is right for you. Where you vacation is very different from where you live. Definitely, use a real estate agent to aid you in your search.