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Truman Annex

Rich in history, quaint in charm.

Truman Annex has primarily been Navy property. To share a bit of brief history, the Navy first came to Key West in 1823. During both the Mexican – American War and Spanish – American War, the Navy further expanded its presence on the island. It wasn’t until World War I that the Navy moved into what is now known as Truman Annex where they built a submarine base. After World War I, this base was used sparingly through World War II and the four decades after.

In 1987, the Truman Annex Parcel was sold to developer Pritam Singh for $17M. The Navy retained the remainder of the Truman Waterfront until 2002 when 33 additional acres were conveyed to the City of Key West. This area is currently being developed as The Truman Waterfront Park with ample open-water green space, an amphitheater, and a children’s splash park!  The remaining 17 acres were retained by the Navy and are used today as headquarters of JIATF-South.

Truman Annex is Key West’s largest gated community which is comprised of seven distinct areas: The Foundry, Mills Place, Harbour Place, Porter Court, President’s Lane, Shipyard Condos and the prestigious private homes of Truman Annex. The renovation and new construction of both historic properties such as The Foundry and the private homes are exquisite. In addition to the beautiful architecture and open streets, Truman Annex is home to the Truman Little White House, where President Harry Truman hosted his working vacations in Key West.

Truman Annex contains both year-round and seasonal residents. Within the Annex, there are certain eligible properties that have a “special residential transient rental permit”. These properties are allowed to rent for a minimum of 7 days up to 26 weeks per year, which makes these locations enticing investments. Off-street parking is currently appraising at an all-time premium.

Travel south on Southard Street to the Waterfront Park and follow the road to the Eco-Discovery Center and the entrance to Ft. Zachary Taylor State Park, the island’s only natural beach where the Atlantic Ocean and the Gulf of Mexico meet. There is a wonderful swimming area with large rocks perfect for the beginning snorkeler. Ft. Zach, as the local’s call it, is a wonderful place to spend your days off, have picnics with family and friends, and take in the breath-taking sunsets we are famous for! 

New Listings in Truman Annex

208 Southard Unit 6, Key West image
208 Southard Unit 6, Key West $892,000

Rarest of the rare, this downstairs Shipyard condo is now for sale. This is one of only six units that flow from side to side (rather than front to back) and is set back ...

  • 2 Beds
  • 2 Baths
  • 605479 MLS
107 Front Unit 217, Key West image
107 Front Unit 217, Key West $3,750,000

Rarely do units become available in the Harbour Place condominiums in Truman Annex, making this property an investor's dream come true, complete with a transient rental l...

  • 4 Beds
  • 4 Baths
  • 605442 MLS
105 Front Unit 119, Key West image
105 Front Unit 119, Key West $1,895,000

This 2 bedroom, 2 bath Harbour Place condo is located on the first floor (2nd floor as parking is on ground level) The first-floor units have the largest decks with plent...

  • 2 Beds
  • 3 Baths
  • 605358 MLS
530 Porter, Key West image
530 Porter, Key West $1,365,000 ▼

Opportunity knocks. Beautifully renovated Truman Annex townhouse- 'Salty Kisses' -conveys with special limited transient rental license in place. Tropical Vibe, light...

  • 2 Beds
  • 2 Baths
  • 605120 MLS
403 Emma Unit B, Key West image
403 Emma Unit B, Key West $1,695,000 ▼

Rare opportunity to own a piece of history in The Truman Annex. This 2 story, 2 bedroom/ 2.5 bathroom villa is located in Mills Place, a quiet and peaceful 20 unit condom...

  • 2 Beds
  • 3 Baths
  • 604868 MLS
620 Thomas Unit 297, Key West image
620 Thomas Unit 297, Key West $895,000 ▼

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. Recently renova...

  • 2 Beds
  • 2 Baths
  • 604825 MLS
64 Front, Key West image
64 Front, Key West $4,800,000

Spectacular home in great location in the award-winning Truman Annex.This beautiful home custom built in 1989, includes five bedrooms and five bathrooms.There are four se...

  • 5 Beds
  • 5 Baths
  • 604823 MLS
620 Thomas Unit 284, Key West image
620 Thomas Unit 284, Key West $849,000

This second-floor, two bed, one bath condominium features soaring vaulted ceilings that make a bright and airy space. Freshly painted interior, tile floors throughout and...

  • 2 Beds
  • 1 Baths
  • 604685 MLS
206 Southard Unit 4, Key West image
206 Southard Unit 4, Key West $875,000

Take a look at Pelican, a nicely furnished and renovated upstairs Shipyard condo. This 2 bedroom/1 bathroom unit is perfectly set up for you to enjoy all that Key West ha...

  • 2 Beds
  • 1 Baths
  • 604658 MLS
518 Emma, Key West image
518 Emma, Key West $3,399,000 ▼

Beautiful Truman Annex. Open floor plan with 3 sets of French Doors that open up to your private tropical Oasis, with a stunning lagoon shaped pool with rock waterfall. ...

  • 4 Beds
  • 3 Baths
  • 604612 MLS
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Key West, FL 33040
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