Carl and I looked for a long time for where we would buy our home for retirement. We knew we would move back to Missouri to be closer to my family, since less of Carl's family in Ohio would be around (Carl's brother moving to Texas, next generation down -- whereever the wind takes them, and the older members likely no longer with us). Our absolute requirements: a home that could be livable on one floor, walkable community, very close hospital and nursing services, fun activities for both early and later retirement. We ruled out senior communities because we like being around a variety of ages, and because these aren't as walkable. We also never considered condos, since even when we can't do the work ourselves, generally, we can hire help for exterior maintenance cheaper than condo fees.
So, really, we were only looking at historic neighborhoods. We might have considered newer developments, if they were able to deliver on our requirements -- but we've never found that to be the case.
This: http://www.hermannmo.com/ is what we wanted for retirement. BTW - if you click the link, DREAM is an acronym for a program in Missouri -- not arrogance (it's described in a link at the bottom, under the Community header). We bought a ranch home on an alley at the end of third street. This allows 1 floor living, when needed. We can walk to everywhere, including the Amtrack station and the park and amphitheater (and a couple of wineries and a microbrewery -- this stuff's supposed to be good for the heart, ya know).
If we were to retire in Ohio, we'd almost certainly stay in our current home in VV. Again, for the walkability, activities, and resources available to us. Our century home has a parlor on the main floor that could be used as a bedroom. We had a bench placed in the shower on the main floor, for an older person to be able to sit on. We wanted to be prepared for my MIL to be able to live with us, if needed. So, (once you get past the exterior steps) -- it's one floor livable, too.
For us, historic neighborhoods were the only thing that fit the bill for retirement. I'm not sure what attracts folks to other types of arrangements, but everyone has their own preferences.
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