I enjoy graphs and spreadsheets, so this won't be for everybody, but what I'd do is make a simple flowchart.
First question -- new home or resale. That answer will limit your search and steer you to the next question of importance to you, which might be price range. The following questions could be things like being close (and how close) to grocery stores, a town square, sports and activities such as golf/softball/bowling/sports pool/regional rec center, etc. Easy golf cart accessibility to other parts of The Villages may or may not be of importance. Once you have a list of preferred villages that meet your requirements, you can focus on specific house features such as model, lot, and bond.
If you have a physical map like justjim suggested, you can draw circles around the areas to get a good overview.
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