We just went through almost three months of searching for a home with pretty much all the things you list. Every pre-owned home we looked at had at least one issue that we did not like, the most common being absolutely no privacy on the lanai. Finding a house, new or pre-owned, with your requirements in that price range will be extremely difficult, if not impossible. I agree with the other posters above that you should be working with both a Villages sales rep and an agent from a MLS brokerage company.
We ended up signing a contract on a new home with a great view and pretty private lanai. We did give up the idea of having a pool, because the least expensive new pool homes are in the $400K and up price range, and the lanais are not private at all, unless you go considerably up in price. There are (or at least were) a couple pool homes around $395K, but the neighboring lanais are within 10 feet.
Best of luck to you!
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