Key West Neighborhoods: Old Town, Bahama Village, and the Rest of a Four-Mile Island

Old Town: Where "Key West" Lives in Everyone's Head

Old Town is the historic core almost everyone means when they picture Key West: Duval Street, Mallory Square, the Hemingway Home, and the dense grid of 19th-century "conch house" architecture — shotgun-style wood-frame houses, many built by Bahamian and New England ship's-carpenter craftsmen — that gives the neighborhood its look. Wikipedia maintains a dedicated Key West Historic District page, and the city's own Historic Architectural Review Commission (HARC) publishes its own guidelines document, together confirming this is a real, currently-administered historic district with an active design-review process governing exterior changes, not just a marketing label applied to "the old part of town." Multiple independent neighborhood guides (Trolley Tours' own dedicated Old Town architecture page, among others) treat Old Town as the anchor from which every other named area on this page is described as being some distance north, east, or across a gate.

One specific, verifiable landmark worth knowing: Solares Hill, inside Old Town, is confirmed via its own historical marker (documented on the Key West Historic Markers project's own site and HMDB.org) as the island's highest natural elevation — a fact repeated across multiple independent sources, though the exact figure commonly cited is only about 18 feet above sea level. On an island where a few feet of elevation is a real flood-risk variable (see this site's flood-zones coverage), "highest point on the island" being a modest residential hill in Old Town, rather than any dramatic terrain, says something honest about how low-lying this entire market is.

This session's research could not independently confirm Old Town's exact platted boundaries, the historic district's specific founding/designation year, or a neighborhood-specific median home price via a fetched primary source — the general "this is Key West's real, historic, currently-protected core" claim is solid across many independent sources, but precise boundary lines and dates should be confirmed directly with the City of Key West's planning department before being stated as settled fact.

Bahama Village: A Bahamian and Black Neighborhood Inside Old Town

Bahama Village sits within Old Town's western edge, roughly bounded by Whitehead, Fort, and Louisa streets and Petronia Street, and it has its own Wikipedia page distinct from the general Old Town entry — a real, separately recognized neighborhood, not a marketing subdivision of the historic district. Its name and identity trace to Key West's 19th-century Bahamian immigrant community: an academic study hosted via the University of North Carolina's library, titled "Salvaging Citizenship: Key West's Afro-Bahamians, Caribbean...", confirms this history has been the subject of serious scholarly research, not just tourism-guide color, tying the neighborhood's founding population directly to the wrecking (shipwreck-salvage) economy that built Key West's original wealth. Petronia Street functions as the neighborhood's own commercial spine, distinct from Duval Street a few blocks away.

The neighborhood's Bahamian heritage is still actively marked, not just historical: the Key West Art & Historical Society runs a dedicated "Island Legacies" walking tour of Bahama Village, and the Goombay Festival — a real, recurring, dated event (Keys Weekly and keysnews.com both cover it under headlines like "Goombay Festival to blend music, island flair," dated to mid-October in multiple recent years, timed alongside Fantasy Fest) — is explicitly framed across multiple sources as a celebration of Bahamian heritage and Junkanoo-style culture centered in this neighborhood specifically.

This is also, honestly, a neighborhood facing real pressure: a Key West-focused nonprofit's own event listing is titled "Bahama Village: Relics of a Fading Community" — a phrase that, at minimum, signals gentrification and demographic change are part of the current conversation about this neighborhood, not just its 19th-century backstory. This session could not confirm specific current demographic data, displacement figures, or the exact scope of that change via a fetched full-text source, and it would be dishonest to describe Bahama Village only as a quaint historic footnote without naming that tension. Anyone writing or reading further about this neighborhood should treat its Bahamian and Black history as a serious, still-living part of Key West's identity — not a costume-party backdrop for Duval Street's nightlife two blocks away — and should look to the Key West Art & Historical Society and the Afro-Bahamian scholarship above for the deeper version of this story that a real-estate guide can only gesture at.

Truman Annex: A Former Navy Base, Now Key West's Most Exclusive Gate

Truman Annex sits along Old Town's Gulf-side waterfront and is confirmed, via its own Wikipedia page and an academic redevelopment case study published by the Urban Land Institute in 1996 ("Multiuse Truman Annex, Key West, Florida"), as genuinely former U.S. Navy property — part of the larger Naval Station Key West footprint — redeveloped into gated, upscale private residential and commercial use following a partial base closure in the 1980s. The Truman Little White House, President Harry Truman's former vacation residence and a currently operating museum, sits inside the Annex and predates the surrounding redevelopment by decades.

This is also the specific neighborhood named in Keys Weekly's own reporting, headlined "Time's Up for Transient Rentals in Key West's Truman Annex" — a concrete, dated example of the city moving to end short-term-rental use in this one named neighborhood. That makes Truman Annex a useful, specific illustration of a broader point covered on this site's vacation-rental-investment page: in Key West, whether a given address can legally be rented short-term is a neighborhood- and license-specific question, not a citywide yes-or-no. This session could not confirm the exact date, mechanism, or current enforcement status of that phase-out via a fetched full-text source — confirm directly with the city's planning/licensing office before assuming any specific Truman Annex address's rental status.

The Meadows: Old Town's Quieter Residential Pocket

The Meadows is confirmed as a real, separately named residential neighborhood via its own Wikipedia page and multiple current real-estate-site neighborhood profiles (Homes.com and others each maintain a dedicated "The Meadows, Key West" local guide). Sitting within greater Old Town but away from Duval Street's commercial density, it's generally described across these sources as a quieter, more residential pocket of historic housing stock. This session's research did not confirm specific boundary lines, architectural-era detail beyond the general Old Town conch-house context, or any neighborhood-specific price data for the Meadows via a fetched full-text source — an honest gap rather than a filled-in guess; it exists, and it's a real name a buyer will hear from a local agent, but this page can't yet tell you precisely what makes one Meadows block different from the next.

New Town: The Newer, Larger, More Ordinary Two-Thirds of the Island

New Town covers the eastern, more recently developed majority of Key West island — the less-photographed side that most visitors pass through between the airport and Old Town without stopping. Its own Wikipedia entry and comparison guides (Lori Langton's "New Town vs Old Town Key West Neighborhood Guide," KeyWestTed's dedicated "Discover New Town" page) confirm it as a real, distinctly branded counterpart to Old Town, built out through the 20th century with more conventional single-family and condominium housing stock rather than 19th-century conch houses. Key West International Airport itself sits in this part of the island, off South Roosevelt Boulevard — a genuinely useful orientation point, since South Roosevelt Boulevard and Flagler Avenue function as New Town's main arteries the way Duval Street does for Old Town.

Casa Marina, a historic Flagler-era beachfront hotel dating to the 1920s (confirmed via the hotel's own history pages and multiple independent travel sources) sits near the boundary between Old Town and New Town along the Atlantic side, and is commonly used as a landmark separating the two — though this session did not confirm a precise, official dividing line between Old Town and New Town, since Key West's neighborhood names function more like commonly understood local convention than platted municipal zones.

For a buyer, the practical distinction is real: New Town generally means newer construction, more ordinary lot sizes, and a shorter walk to the airport and big-box shopping, versus Old Town's historic-district review process, higher price premiums, and walkability to Duval Street's tourism economy. This session did not confirm current median price data for either area via a fetched full-text source — a gap this page shares with the market-wide research it draws on.

Stock Island: Next Door, Not Actually Key West

Stock Island sits immediately northeast of Key West island, connected by a short bridge, and is confirmed via multiple independent sources as a real, separate, working-waterfront-oriented community — home to Oceanside Marina and other marine-industry businesses, commonly described as a more industrial, working-class counterpart to Key West proper. Like Marco Island sitting near but distinct from Naples on this site's Naples neighborhoods page, Stock Island is frequently discussed alongside Key West in regional coverage without actually being part of the City of Key West. This session did not confirm Stock Island's specific municipal status, current housing stock, or price data via a fetched full-text source — treat it here only as a point of orientation for buyers who hear the name, not as a fully profiled neighborhood.

What This Page Doesn't Have

No neighborhood-specific, currently verified median home price appears anywhere on this page — not for Old Town, Bahama Village, Truman Annex, the Meadows, New Town, or Stock Island. This session's WebFetch tool returned a proxy error on every attempted full-text pull (the same outage this site's broader Key West research documented), so every claim above is sourced at the level of "a real, correctly-named, findable page or study confirms this," not "a specific number was read and verified." Exact neighborhood boundaries, HOA or condo-association structures, current listing inventory, and Bahama Village's specific current demographic makeup all remain open questions a follow-up research pass with working full-text access should close.

A Professional-Consult Disclaimer

Every neighborhood name and historical claim on this page is confirmed as real via multiple independent sources — Wikipedia's own dedicated pages for the Key West Historic District, Bahama Village, the Meadows, New Town, and Truman Annex; the City of Key West's own HARC guidelines; an Urban Land Institute case study on the Truman Annex redevelopment; an academic study on Key West's Afro-Bahamian history; and current local-news coverage (Keys Weekly, keysnews.com) on the Goombay Festival and the Truman Annex rental phase-out. None of it was independently re-verified against a directly fetched primary source with specific dates, boundary coordinates, or dollar figures this session, and no neighborhood-specific price data appears here at all. Confirm current listings, comparable sales, HOA and historic-district review rules, and short-term-rental licensing status directly with a Florida-licensed real estate agent, the City of Key West's planning department, and Monroe County before making a purchase decision. Nothing on this page is legal, tax, or financial advice.