We are in The Villages 2 1/2 years now and we have owned pools before moving here. We had a pool put in during our build here and we use it all the time. As far as maintenance, the only maintenance we have is to write out a check to T&D, sure wish they would switch over to auto pay. Love the fact we can swim in our pool whenever we want to and we don't have to pack up towels, sunscreen, hats, Kindles, drinks, snacks and so on. We also don't have to sit by a pool and listen to endless conversations by people on their cell phones. If you can afford it, go for it.
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