Old Town (Key West), FL
America's southernmost residential district, pre-1940 Conch architecture, Duval Street + the cruise port, no high-rises by law.
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.
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)?
Local agents in Monroe County know the inventory, the HOA rules, the school zones, and the negotiation patterns. Tell us what you're looking for, and an agent will follow up.
Thinking about Old Town (Key West)?
Tell us your budget and timeline. A licensed agent from QA Onboarding Test will follow up about homes and financing. Only a lender can pre-approve you for a loan.
Frequently asked
Common questions about Old Town (Key West).
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.
Median price and days on market are calculated from active listings across the whole city named on the figure, or this place where no other city is named, and they are a snapshot from the "as of" date above. Any prices in the guide's text are editorial and can differ. Numbers shift constantly in active markets, for the most current view of any specific property, ask the agent we match you with. We aim for honest, not flattering.
Verify school zoning for your specific address with the school district. Property tax estimates assume primary-residence homestead and standard millage rates as of the publish date.