Neighborhoods
Every part of Key West has a different character — from Old Town’s historic density to Sunset Key’s private-island seclusion. Filter by Condo or Waterfront, or explore each neighborhood to see active listings and what makes it distinct.
Figures use the same all-residential neighborhood snapshots as Market Pulse, refreshed twice daily. Prices are median asking prices, not starting prices.
Old Town
69 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
Old Town is Key West's historic core — narrow lanes lined with 19th-century Conch houses, gingerbread trim, and mature tropical landscaping, all within walking distance of Duval Street and Mallory Square.
Casa Marina
7 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
Casa Marina takes its name from the historic resort at its center and covers the beachfront district on Key West's Atlantic side. It's the closest thing the island has to a true beach neighborhood, with wider lots, mature landscaping, and direct or near-direct beach access.
The Meadows
10 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
The Meadows is a historic residential pocket within Old Town, distinguished by its dense tree canopy and Bahamian-influenced cottage architecture — smaller in scale than the grander Casa Marina estates, but just as historically protected.
Truman Annex
6 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
Truman Annex occupies what was once a naval property at the island's western tip, redeveloped into one of Key West's most exclusive gated communities. Streets are wide, quiet, and shaded, with direct proximity to Fort Zachary Taylor's beach and the Truman Waterfront.
Sunset Key
1 Active ListingMarket Pulse · Oct 11, 2026, 9:00 PM ET
Sunset Key is a private island a short ferry ride from Key West Bight, developed exclusively with luxury homes and a resort-operated cottage collection. There are no cars, no through traffic, and no public access — privacy is effectively the product.
Shark Key
2 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
Shark Key is a small, gated island a short drive from Key West proper, developed exclusively with large waterfront estates set among protected mangrove channels. Access is restricted to residents and their guests.
Representative PhotoKey Haven
7 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
Key Haven sits just off Key West proper, connected by a short causeway — technically its own small island, and noticeably quieter and more suburban than anything in town.
Midtown West
29 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
Midtown West sits toward the center of the island, built out with more conventional single-family homes than Old Town's historic Conch construction — practical, residential streets rather than tourist-facing ones.
Representative PhotoMidtown East
30 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
Midtown East covers the eastern stretch of Key West's Midtown area, generally closer to the airport and the island's shopping corridors than Midtown West.
Representative PhotoNew Town
62 Active ListingsMarket Pulse · Oct 11, 2026, 9:00 PM ET
New Town is the newer, eastern half of Key West — developed later than Old Town, with wider streets, more conventional construction, and easier parking, and home to the airport and most of the island's larger shopping.