Search for Homes in the Truman Annex

The Truman Annex Homes for Sale

The Truman Annex used to be a Navy Base. It's named after our former President Harry S. Truman because that was his winter retreat home and it's located in Old Town Key West. You should check out the Little Whitehouse if you haven't already. If you are familiar with Key West than you know this is a convenient location in Old Town because you are walking distance to Duval Street, Fort Zachary Beach and other fine amenities this island has to offer. This is a private gated community and has different homes/styles to choose from.

In the historic Old Town of Key West, Florida, you’ll find the prestigious district of Truman Annex, named after President Harry Truman it is the home of the “Little White House.” The Little White House is a grand historic home built in 1890, was used as the winter retreat of the President in the late 1940’s, and today it is known as the Harry S. Truman Little White House Museum. Truman Annex is a 6-block planned luxury community of tropical beauty designed to encapsulate the unique spirit of historic Key West. The neighborhood is found on the western edge of Old Town and is bounded by Southard, Front and Whitehead Streets.

Truman Annex real estate consists of multi-million dollar Key West homes, condos, and townhouses within several distinct neighborhoods. You can find historic Italian and Greek Revival homes renovated as gorgeous luxury mansions with white picket fences and perfectly landscaped lawns. At the southern end of Truman Annex, you’ll find a collection of Southern Cottage style homes with tin roofs and porches. Adjacent to Mallory Square there is a delightful planned subdivision with a conch cottage design, free-standing homes, and condos with access to picturesque gardens and community swimming pools.

No matter which Truman Annex neighborhood you choose, you'll be in a prime location within walking distance to Mallory Square, Duval Street and other Key West attractions, including the beach at Fort Zachary Taylor State Park. Other neighborhood points of interest include the Mel Fisher Treasure Museum, US Coast Guard Cutter Ingham Maritime Museum, and the Audubon House and Tropical Gardens. The meticulous tropical landscaping gives the community a picturesque park-like ambiance and along upper Duval Street, you’ll find some of Key West’s best entertainment, shopping, and dining. Truman Annex is a sought-after address for high-end vacation rentals and permanent residents desiring to live near the heart of Key West. It is also a popular destination for homebuyers attracted to the exciting culture of Key West and its rich history and heritage. If you would like to learn more about the homes for sale in Truman Annex of Key West, Florida, please don’t hesitate to contact us for more information.

Truman Annex's Newest Listings

2 Beds ⋅ 2 Baths ⋅ 602665 MLS

A Transient Licensed property, 510 Porter Lane is a 2bed / 1.5 bath Townhome located in the highly desirable Truman Annex. Walking distance from Duval Street, the Truman Waterfront Amphitheatre, restaurants, bars, and the many other attractions within Old Town Key West. In addition, a deeded covered parking spot conveys with property, and is conveniently located just a few steps from the unit. Other attractive elements include being located within X-Flood Zone, hurricane shutters for windows and doors, relatively low insurance costs, etc. This property is currently an active vacation rental.

510 Porter, Key West

6 Beds ⋅ 6 Baths ⋅ 602640 MLS

Available for the first time in over a decade, this unparalleled rare island sanctuary awaits the most discerning buyer! Located in the exclusive gated Truman Annex, this distinctive 6-bedroom 5.5 bath grand estate boasts endless amounts of charm and character. Lauded for its breathtaking ocean views, sunrises and sunsets, this spectacular, expansive estate is situated on a 10,000 square foot double lot surrounded by abundant tropical vegetation and lush foliage. Historic in nature, the Truman Annex area served as President Harry S. Truman's winter home where he dealt with pressing issues of his presidency. This property will be transferred with a Truman Annex Transient Rental License, a most valuable commodity, allowing for your return on investment. The main house features 6 bedrooms and 5.5 bathrooms. A storied widow's walk is located on the top of the 3rd floor and is easily accessible with the push of a button. With over 800 square feet of covered porches, this home offers impressive indoor and outdoor living. A great veranda overlooks the estate's landscape with lush green grass, exotic trees, and a 30 plus foot heated lap pool. A separate guest house, garden gazebo, art studio, and carport, parking for 4 vehicles complete this trophy estate. Unprecedented ocean and city views can be seen from the second-floor balconies as well as the widow's walk. Located on a peaceful cul-de-sac, yet moments away from all the happenings the island is renowned for. This highly coveted gated community is close to an array of local attractions, as well as high-end galleries, shops, and restaurants. The estate is in close walking proximity to the island's most beautiful beach, Fort Zachary Taylor State Park, which is steeped in history and affords a magnificent setting for bird watching and fishing. This highly acclaimed, private, sought-after property is waiting for you to call it home.

504 Noah, Key West

5 Baths ⋅ 602438 MLS

Now available is a majority interest in the Courthouse Business Center. Offered are 11 of the 37 individual units. These popular one-room offices were built new in 2001. Located in Old Town Key West at the entrance of Truman Annex at the corner of Thomas and Southard Streets. Offices are on both 1st floor and 2nd floors, building provides shared kitchenettes, restrooms, and a shared parking lot. Office 302-101 is on the first level next to the main entrance with 171sq.ft. Units can be purchased individually.

302 Southard Unit 101, Key West

1 Beds ⋅ 1 Baths ⋅ 602168 MLS

This one bedroom condo is a little slice of paradise. It's located in the gated community of The Shipyard in Truman Annex, so you're close to all the action but far enough away that you can escape it when needed. Plus, it's an end unit with extra windows for natural light, and it has been recently renovated with granite countertops and stainless steel appliances in the kitchen and an updated bathroom. You'll love relaxing on the large, private rear deck after a long day - or better yet, watching Fantasy Fest from your front row seat on Southard Street! The condo is offered furnished, so you can just move right in. Located just steps from the community pool, Duval Street, and the Truman waterfront. This unit has a special Truman Annex Transient license and a private parking space.

202 Southard Unit 11, Key West

1 Beds ⋅ 1 Baths ⋅ 601963 MLS

Ground floor, one bedroom, one bath condo in Shipyard Condominiums. Mexican tile floors, crown molding, and recently painted with an updated kitchen. This is a larger floorplan than most one-bedroom units with an expanded living area. Two sets of French doors open to the large multi-level rear deck. Includes one off street, assigned parking space. The community pool is a short walk away as is the Truman Waterfront City Park. This is not currently used as a vacation rental, but the special Shipyard / Truman Annex transient rental license can be reactivated.

620 Thomas Unit 168, Key West

2 Beds ⋅ 1 Baths ⋅ 601682 MLS

This is a delightful Shipyard unit on the ground level located at the back of the Truman Annex community with a spacious back deck facing the outer mole. The living room and master bedroom have French doors that flow out onto the rear deck. Enjoy a quiet and tranquil setting while you are within walking or biking distance to many Key West attractions and fabulous restaurants. This has a special Truman Annex Transient license with reservations in place and is turnkey. This unit also has its own designated parking space.

620 Thomas Unit 171, Key West

2 Beds ⋅ 1 Baths ⋅ 601443 MLS

First floor Shipyard condominium features 2 bedrooms and 1 bath. Updated kitchen with stainless steel appliances, granite countertop, and updated bath with shower. Large rear deck provides plenty of room for outdoor living and provides easy access to the community pool that is located close by. Convenient, assigned parking space, just steps from the front door. Impact windows and French door. This property has the special Truman Annex / Shipyard transient rental license.

620 Thomas Unit 186, Key West

2 Beds ⋅ 2 Baths ⋅ 601030 MLS

2 bedroom, 2 bath upstairs spacious unit in Truman Annex with one assigned parking space. Bright and Airy floor plan with cathedral ceilings, and balcony. Located within walking distance Duval street, Truman Waterfront Park and Fort Zachary Taylor State Park. This property is a perfect vacation home or investment property. It does have a transient license which allows weekly rentals. The owner has rented it out as a long term rental since 2018. Sold furnished turn key.

620 Thomas Unit 297, Key West

4 Baths ⋅ 600635 MLS

Now available is a majority interest in the Courthouse Business Center. Offered are 11 of the 37 individual units. These popular one-room offices were built new in 2001. Located in Old Town Key West at the entrance of Truman Annex at the corner of Thomas and Southard Streets. Offices are on both 1st floor and 2nd floors, building provides shared kitchenettes, restrooms, and a shared parking lot. Size of the units range from 123sq.ft. - 230sq.ft., total 1675sq.ft. Units can be purchased individually.

300-302 Southard Unit 11 Units for Sale, Key West