Truman Annex

Truman Annex offers a combination that's extremely difficult to duplicate anywhere else in Key West: privacy, beautiful architecture, tropical landscaping, parking, amenities, and true Old Town walkability.

Residents enjoy:

• Gated residential setting

• Beautifully maintained tropical landscaping

• Classic Key West and historic architecture

• Community pools within certain sections

• Assigned or private parking with many properties

• Private courtyards, porches, and outdoor living spaces

• Immediate access to Truman Waterfront Park

• Proximity to Fort Zachary Taylor State Park and beach

• Walking distance to Duval Street

• Walking distance to Mallory Square

• Easy access to the Historic Seaport

• A wide range of property styles, sizes, and price points

The neighborhood feels peaceful and residential once inside the gates, yet restaurants, galleries, beaches, nightlife, and many of Key West's best-known attractions are only blocks away.

One of the most important things to understand about Truman Annex is that not every property is the same type of ownership.

Shipyard Condominiums

Shipyard is one of the largest and most recognizable sections of Truman Annex. It consists of condominium residences arranged among tropical landscaping, pedestrian paths, and a community swimming pool.

Shipyard offers some of the more approachable opportunities to own within Truman Annex and is particularly popular with buyers seeking a smaller second home or Old Town property.

Harbour Place

Harbour Place is a waterfront condominium community within Truman Annex. Residences are generally larger than those found in Shipyard, with select properties offering exceptional water and sunset views.

Its waterfront setting and location near Mallory Square make Harbour Place one of the premier condominium addresses within Truman Annex.

Mills Place

Mills Place is a condominium community within Truman Annex offering larger residences in a beautifully landscaped Old Town setting.

Its residences offer a different ownership and living experience from the smaller condos at Shipyard, giving buyers another condominium option within the larger Truman Annex community.

President's Walk / President's Lane

President's Walk offers townhome-style residences with classic Key West architectural details, private outdoor spaces, porches, and convenient access to the surrounding Truman Annex amenities.

These properties provide more of a traditional home experience while retaining the benefits of living within the gated Truman Annex community.

The Foundry

The Foundry is one of the most architecturally distinctive sections of Truman Annex. Historic former naval buildings were adapted into multi-level residences, giving these homes a character unlike the traditional Conch-style architecture found throughout much of the neighborhood.

Many Foundry residences feature multi-level living and private courtyards.

Private Homes

Truman Annex also contains individually owned private residences ranging from charming Key West-style homes to substantial luxury properties.

Depending on the property, features may include:

• Private swimming pools

• Tropical gardens

• Off-street parking

• Porches and balconies

• Larger floor plans

• Private courtyards

• Outdoor entertaining areas

These homes provide buyers with the privacy and independence of a single-family residence while remaining within the Truman Annex master community.

Location is one of Truman Annex's greatest advantages.

The neighborhood sits in the heart of Old Town while providing a quieter, gated residential environment just blocks from many of Key West's most popular destinations.

Nearby you'll find:

• Duval Street

• Truman Waterfront Park

• Fort Zachary Taylor Historic State Park and beach

• Harry S. Truman Little White House

• Mallory Square

• Historic Seaport

• Custom House Museum

• Restaurants, galleries, shopping, and nightlife

For many Truman Annex owners, a car becomes optional rather than necessary. Walking and biking are part of everyday life, while dedicated parking associated with many properties provides a valuable convenience when a vehicle is needed.

Rental rules within Truman Annex are not uniform throughout the entire community.

This is particularly important for buyers considering rental income.

A property may be subject to:

• Truman Annex Master Property Owners' Association requirements

• An individual condominium or homeowners association

• Property-specific governing documents

• City of Key West zoning and licensing requirements

• Transient rental licensing requirements, when applicable

Some Truman Annex properties may qualify for shorter-term rentals, while others require monthly or longer rental periods.

Buyers should never assume that because one Truman Annex property can be rented a certain way, another property within the community can be rented the same way.

In certain Truman Annex properties, yes. In others, no.

The ability to offer weekly or other short-term vacation rentals depends on the specific property, its association rules, City of Key West regulations, and applicable transient rental licensing.

Other properties within Truman Annex are better suited to 30-day monthly rentals or longer-term leases.

For buyers interested in rental income, verifying the rental rights of the specific property before purchasing is essential.

Truman Annex can be an excellent choice for buyers seeking:

Full-time residence

Luxury second home

Seasonal residence

30-day monthly rental investment

Short-term rental investment in qualifying properties

Long-term rental investment

Walkable Old Town lifestyle

Because Truman Annex contains several different property types and rental structures, investment potential can vary significantly from one property to another.

Before purchasing in Truman Annex, buyers should review:

• Truman Annex Master Property Owners' Association documents

• Governing documents for the individual association, when applicable

• Association financial statements and reserves

• Current rental restrictions

• Transient rental license status, when applicable

• Insurance responsibilities

• Owner versus association maintenance responsibilities

• Parking rights and assigned spaces

• Pet policies

• Architectural restrictions

• Any applicable historic preservation requirements

• Current or planned capital improvements and assessments

Understanding which association governs the property and which expenses and responsibilities belong to the owner is especially important in Truman Annex.

Truman Annex is one of those communities where saying, "I want to buy in Truman Annex" is really only the beginning of the conversation.

A Shipyard condo, a waterfront residence at Harbour Place, a Mills Place condo, a Foundry residence, a President's Walk home, and a private single-family home can all have a Truman Annex address, but they offer very different ownership experiences, price points, maintenance responsibilities, and rental opportunities.

What they share is an exceptional location. Truman Annex gives you something very special in Key West: a beautifully maintained, gated residential neighborhood right in the heart of Old Town. You can walk to dinner, Duval Street, Mallory Square, Truman Waterfront Park, or Fort Zachary Taylor and then return home to a neighborhood that feels surprisingly peaceful.

For buyers interested in rental income, this is also a community where the details really matter. I never recommend assuming that because one Truman Annex property can be rented a certain way, another one can too. We need to look at the association, governing documents, and licensing status of the specific property.

That's one of the things I love about Truman Annex: there isn't just one way to own here. Once we know whether your priority is location, waterfront, rental flexibility, more living space, a private home, or simply finding the best opportunity within the neighborhood, we can narrow the search considerably.