Exclusive gated community surrounding the Little White House, with pristine streets and harbor views.
Truman Annex is Key West's most prestigious gated community, home to President Harry Truman's Winter White House. This ultra-exclusive neighborhood features impeccably maintained streets, private docks, and stunning views of the Key West Harbor. Properties here are among the island's most coveted—elegant townhomes, condominiums, and estate residences with resort-style amenities. Residents enjoy 24-hour security, a private beach, tennis courts, and the tranquility of a protected enclave just steps from downtown.
Price Range
$3M - $12M
Property Types
Townhomes, Condos, Estate Residences
Lifestyle
Exclusive, Secure, Waterfront
Photo Gallery
Market Insights
Median Price
$5.8M
Days on Market
90-120
Inventory
Very Low (1.2 months)
Price Trend
+5.8% YoY
Walkability Scores
Walk
91
Transit
48
Bike
85
Walker's Paradise — daily errands do not require a car
Flood Zones & Insurance
FEMA Zones
X, AE (varies)
Insurance Note
Predominantly Zone X (preferred risk, lower premiums). Some AE zones nearer the harbor. Flood insurance required in AE zones with federally backed mortgages; recommended in X. Average annual: $1,200-$3,800
Buyer Intelligence
Architectural Character
Neoclassical frame vernacular and Key West Conch-style architecture, rebuilt to period standards after the Navy's departure in the 1980s. The development is architecturally cohesive with strict design guidelines maintained by the Truman Annex HOA.
Vacation Rentals
Not PermittedTruman Annex prohibits short-term vacation rentals. The community is restricted to owner-occupancy and annual leases only. This policy protects the residential character and is enforced by the HOA — buyers seeking rental income should look elsewhere.
HOA
YesHOA fees range $800–$2,200/month depending on property type and size. Fees cover 24-hour security, landscaping, private beach maintenance, tennis courts, and community insurance contributions. A healthy reserve fund is maintained.
Parking
Each unit includes one or two assigned parking spaces within the gated community. Visitor parking is available inside the gate. This is one of the few Old Town-adjacent neighborhoods where parking is a genuine non-issue.
Area Schools
Gerald Adams Elementary
Horace O'Bryant Middle School
Neighborhood Highlights
Gated Community
Truman Little White House
Harbor Views
Ultra-Private
24-Hour Security
Private Beach
Nearby
Restaurants
Attractions
Marinas & Waterways
Sunset Key Marina
245 Front St, Key West
Key West Harbor Marina
Front St, Key West
Interested in Truman Annex?
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