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

$1,640,000
2 Beds 3 Baths 603658 MLS
Vacation rental opportunity with an active transient rental license! Imagine waking up in a living Key West travel brochure. Sun dancing through shady treelined streets of historic homes, with smiling tourists heading to the beach on bicycles. Lazy lanes with colorful roosters scratching around. History buffs enjoying the neighboring Little White House Museum. Mallory Square, host to the famous daily sunset celebration, and the hub of all activity in Key West, Duval Street, are just a couple of blocks outside your front door. See popular music headliners perform at the nearby amphitheater or stroll over to the popular Green Parrot to hear their famous afternoon sound checks. Welcome to The Foundry, an intimate setting of townhomes in a restored postwar Naval red brick building in The Truman Annex. #23, a lucky number to many and hopefully now yours, is available for your purchase with instant rental income. Located on the preferred Front Street side of the complex, #23 offers an amazing contemporary floor plan on 3 floors. The open concept main living area is light saturated with an impressive floor to ceiling glass entry and 11 foot tall ceilings. Dedicated to the 2nd floor is the master suite leading to a private secluded treetop balcony. Guests enjoy the entire top floor suite for perfect bedroom separation. Entirely furnished with all necessary appointments and accessories, the property is turn key ready for your occupancy or to continue to rent with skilled property management and marketing in place. Included in the sale is a Truman Annex Transient Rental License allowing for 25 weekly rentals per year with unlimited monthlies. Convenient to #23 is assigned parking, while close by is a swimming pool for Foundry owners and their guests. A 3D tour is available soon for your virtual showing requests or when guest occupied. $1,640,000

101 Front Unit 23, Key West

$7,900,000
5 Beds 4 Baths 603583 MLS
Incredibly private & spectacular property on one of the largest lots in the gated community of Truman Annex, an absolutely stunning old town estate! A wall of tropical foliage surrounds the home providing privacy & a lush atmosphere for this remarkable 5BR/4BA compound style home on a huge 14,000 SF lot. A showstopper covered pavilion surrounded on 3 sides by the inviting waters of the swimming pool creates a serene island oasis for all your entertaining desires. Beautifully renovated through-out it features 3 separate dwellings blending traditional & contemporary architecture to provide luxurious yet comfortable living. The great room has cathedral ceilings, fire place, handsome mahogany floors & a wall of French doors that open out to the gardens, pool, outdoor kitchen and additional living quarters. The contemporary chef's kitchen is top to bottom total class, beautifully up-fitted for the most discerning user. Custom Neff cabinets and granite counters plus the best appliances complete the feeling of efficient sophistication. Gorgeous marble & onyx bathrooms, a stunning primary suite w/ an amazing bath w/ his & hers sides, impressive custom built-in closets & Robern mirrored cabinets. Lounge in your large private screened porch off the primary to sip that morning coffee. The guest cottage built a few years ago has soaring ceilings, an ensuite bath & its own front porch that is tucked into a quiet corner of the property. The main house has 1 ground floor bedroom w/ full bath & 2 upstairs bedrooms w/ Jack & Jill bath, a mezzanine, porch & reading nook. Host family & friends at your large outdoor bar w/ a full kitchen. Enjoy great decks & brick paths that wind through lush tropical gardens highlighted w/ irrigation & landscape lighting. Lots of storage, 2 washers/dryers, covered 2 car carport w/ additional assigned parking for 2 or more cars. This is one of THE signature properties in the Truman Annex. Truman Annex Special Transient Rental License is included.

101 Admirals, Key West

$9,999,999
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 1300 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