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I'm in love with where I live (Seattle area) so this is a no-brainer for me. Having said that, these are three nice houses, and the Florida one is a close runner up -- perhaps for winter visits.
This is kinda tough. I was initially pretty primed for the Keys house. It's beautiful outside, and has the dock with space for 2 boats. Gorgeous. But the architecture itself? Pretty generic, ticky-tacky vacationland/open-plan/cheap materials, plus it looks like it's in a boring community, even if it's in the Keys. There are the Keys and then there are the Keys, and this looks like it's in a Gated Community Boringville Retiree part of the keys, not laid-back Jimmy-Buffet-Sunset-Party-Land keys. So, I think I'd go for Seattle as the best combination of house + view + community. The PA house is really nice, great history, well preserved, but you'd be stuck in Dullsville there too. It's the kind of place you'd live because you got an awesome job there, so you found an awesome old house, not because it's an awesome place to be in and of itself. Seattle FTW.
Actually, I want to live in Boringville. I plan to spend my declining years studying some obscure subject, yet to be determined, and writing things on the typewriter that nobody wants to read. Screw community.
The Florida place would be my distant second. It looked cozy, but I'm not a big fan of Florida, and that pic of the walkway out to that raised platform really killed any consideration for me. The enclosed pool looked pretty dumb, too.