It's an interesting question, this, and one I have recently discussed with a friend of mine. I retired last year, aged 56. I was made redundant and decided that I wouldn't attempt to get another job, on the grounds that having a little less money than I had planned was a price well worth paying for stepping off the treadmill.
So, while I can't afford to live wherever I like - at least, not in a property that I might want - there aren't many places that would be impossible for me. And I certainly will not stay indefinitely in precisely my current location. But as yet, I haven't gone anywhere, for this reason. In my view, one's life consists more of people than places. I would be extremely cautious about moving somewhere I knew nobody - breaking, or at least weakening, existing social ties and having to create a completely new social circle. In particular, I have a distaste for the idea that I might end up spending most of my time with other retired people, for no better reason than that we all had time on our hands.
So, my current solution is to remain in the community I have a stake in, but to explore alternatives. I'm going to spend three months in Southern Spain this winter, in a place where I know a few people. The weather will allow me to ride every day, and I'll take the opportunity to improve my Spanish, and thus increase my options for the future. I suspect that I shall retain a base somewhere near my current location, but travel - and that wherever I am living, I'll spend at least two or three months each year touring on my bike.