Key West seems to be a thriving community. Pedestrians walk the streets at all hours, at least in the Old Town area. There are signs of its former depressed state in the form of paint deprived wood frame structures down nearly every side street. There are also new high end residential areas, like Truman Annex a redeveloped area of the Key West Naval station.
The only disappointing area for me was the area around Mallory Square which is taking on a Disney like glow with historic buildings, polished up adjacent to new tourist oriented structures and giant cruise ships. Even its not that bad, yet, with the Custom House and other old structures anchoring the area.
Outside the main tourist areas of Old Town the same sleepy ramshackle Key West seems to continue on. Small houses stand next to large residences, there is a trailer park one block off Duval street. Mixed into all of this is a veritable architectural history of Florida. Deco retail building on Duval Street, Antebellum buildings, Turn of the Century retreats brought in with the coming of the railroad, Fifties Era post war motels brought in with highway access, Sixties ranch retirement homes all chock a block with one another. Somehow it all hangs together.
One thing I did notice is that recent chain outlets appear to be somehow regulated. None of them resemble their typical trade dress. New Construction seems to conform to a prettified idea of what Key West should look like. I'm not so sure that is such a good idea.
One thing is apparent. property values have exploded. I saw a hand written "For Sale by Owner" placard offering a 3BR 2BA condo in a frame building for $1,249,000. I saw what looked to be 2 BR cottages, new construction in Old Town for $549,000 to $625,000. The Hemingway House on over an acre of land was last sold in 1961 after his death for $80,000. In 1965 my parents sold a three bedroom house in West Virgina for $23,000 and bought a brand new four bedroom house outside New Orleans for $35,000. The same house by the same builder in Lakewood North, under construction at the same time, would have cost at least $50,000.