Y’all already know that I think North Roosevelt is butt ugly. What with its mishmash of deteriorating parking lots, sad-looking landscaping, profusion of signs, abandoned mid-century concrete buildings and auto lots spreading like Brazilian Pepper, the boulevard is hardly the answer to “What does Key West look like?”

But, yeah, that’s exactly what Key West looks like.

Key West also looks like Midtown and New Town, built mostly on fill from the Navy’s dredging around the island. That’s where locals moved between the 1950s and 1970s, when the lure of a new house and yard with plenty of room and modern amenities outweighed the headaches of maintaining old homes with cramped spaces, ancient plumbing and unsteady foundations.

Key West looks like the Meadows, with its wild mix of vintage Conch cottages, mid-century stuccoed block rectangles and the occasional historic or historic look-alike grand dame. Named, as the story goes, by local real estate agents who had no idea what to call this collection of city blocks east of White Street, north of Truman and west of Eisenhower, the Meadows’ Key West ambience is held together by white paint and green growing things.

When those neighborhoods weren’t enough, we built Key Haven, which uses the Key West 33040 zip code, but actually is an unincorporated community on Raccoon Key in Monroe County. Like the south side of Stock Island, Key Haven is home to folks who mostly identify themselves as from Key West, but they can’t vote in city elections and they’re governed by Monroe County.

Key West was supposed to have completed a Key Haven annexation study by 2017, and by 2020 prepared another for the south side of Stock Island. (The north side — think golf course, hospital and College Road — is already inside the city limits.) The last we heard about those studies was in 2024.

As then-Planning Board Chair Sam Holland told a local newspaper in April 2024: “Seven out of 10 homes in Key West these days are owned by people who don’t live anywhere near Key West. Meanwhile, there are so many local business owners, general managers and people with major stakes in what happens in Key West living in Key Haven, but they can’t vote in city elections.”

How do we know something doesn’t look like Key West?

So let’s go back to my original question: What does Key West look like? And we answer it every time a proposed renovation or major development project drop its AI-generated drawings, “But that doesn’t look like Key West.”

I’m of the mind that Key West looks exactly like what we are, a weirdly cobbled together accumulation of architecture that changed each time residents felt flush with cash and an itch to expand. In 1965, worried that Old Town would no longer, well, look like Old Town, locals created the Old Island Restoration Foundation, which continues today. In 1986 the city’s official Historic Architectural Review Commission replaced OIRF and the city extended the boundaries of its historic district, listed in the National Register of Historic Places. Pretty much all of Old Town and the Meadows now falls inside the historic district, except for the small Casa Marina neighborhood and Truman Annex.

That gives HARC the power to determine your building heights, house, door and shutter paint colors, roof coverings and whether you can paint your fence pickets rainbow colors. (Yes, you can, HARC said Sept. 23, but don’t grab the paintbrush just yet: The new rule still needs approval from the Planning Board, the City Commission and, alas, the state, a process that could take six-nine months.)

Whether we want to admit it or not, there’s really no such thing as THE Key West look. Marketing folks have been relentless with postcards of white wood houses, metal roofs, black shutters and 4-foot picket fences, just like they’ve done their darnedest to convince us and the tourists we’ve got crystal-clear water and white sandy beaches.

All those HARC rules and ad campaigns keep Key West from becoming Marco Island and Miami Beach. Not for us those giant glass towers and gated beach access. That’s a good thing because it’s kept us Key West — and not Florida.

In truth the entire historic district is the culmination of 200 years of figuring out how to live on an island 150 miles from the mainland and then tying most of it together with gallons of white paint, acres of green growing things and an occasional pop of color. North Roosevelt ain’t gonna look like a postcard, so I’ll settle for “At least it’s got palm trees and sun-sparkled water on one side.”

Learn more

https://www.achp.gov/preserve-america/community/key-west-florida

https://www.cityofkeywest-fl.gov/427/Historic-Architectural-Review-Commission