Old Town (Key West), FL
America's southernmost residential district — pre-1940 Conch architecture, Duval Street + the cruise port, no high-rises by law.
Data as of 2026-04-01. Refreshed quarterly.
Old Town Key West is the original residential district — roughly 30 blocks of pre-1940 Conch-style architecture (board-and-batten Bahamian-influenced cottages on raised foundations). The Old Town Historic District is one of the largest preserved 19th-century neighborhoods in the United States — 3,000+ contributing structures.
Buyer pool: a mix of seasonal-residence buyers (heavy Northeast + Midwest), vacation-rental investors (when permitted), artists + writers (Hemingway-era cultural fabric persists), and a smaller permanent local population. Year-round population shrinks to ~7,800 from a peak winter + cruise season multiple times that.
Pricing depends heavily on dock access (some properties have private canal/Gulf access), historic-district restrictions (HARC review), vacation-rental permit status (Monroe County restricts STRs aggressively), and proximity to Duval Street vs quieter Bahama Village.
What makes it distinctive
Things that move the needle.
HARC review (real)
Historic Architectural Review Commission governs every exterior change in the 3,000-structure historic district. Even paint colors require approval. 12-20 week permit timelines on most renovations.
Vacation-rental restrictions
Monroe County restricts STRs to specific zones. Many properties cannot legally be Airbnb'd. Verify permit + transferability before buying as an investment.
Hurricane reality (Cat 4+ exposure)
Key West is in the highest-frequency hurricane corridor in the US. Insurance + structural verification non-negotiable. Hurricane shutters + raised-foundation status are required-due-diligence items.
No high-rises by law
Key West building height limited to 40' citywide. Preserves the Conch-architecture skyline + means no high-rise condo product exists. Limits supply at the high end.
Want to buy in Old Town (Key West)?
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Get matched in Old Town (Key West)
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Frequently asked
Common questions about Old Town (Key West).
Old Town vs New Town Key West?
Old Town: pre-1940 historic stock, walkable to Duval, premium pricing. New Town: 1950s-onwards suburban-style, less character, more car-dependent, materially cheaper. Most buyers want Old Town's character; investors sometimes pick New Town for cap rates.
Are short-term rentals worth pursuing here?
Only at properties with grandfathered or transferred STR permits. New STR permits are essentially unobtainable; existing permits can transfer with the property but verification is critical pre-purchase. A non-STR-permitted property has dramatically different cash-flow math.
Data is hand-curated by REHL editors from a mix of public records, MLS feed inputs, and listing aggregator analytics. Refreshed at least quarterly; the "as of" date above is current. Numbers shift constantly in active markets — for the most current view of any specific property, ask the REHL agent we match you with. We aim for honest, not flattering.
School ratings draw from a blend of state assessments and public school-rating databases; verify zoning for your specific address before relying on these scores. Property tax estimates assume primary-residence homestead and standard millage rates as of the publish date.