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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

2 Beds ⋅ 1 Baths ⋅ 620303 MLS

Freshly relaunched and ready for its next chapter, this beautifully maintained 2-bedroom, 1-bath condo in Shipyard offers the Key West lifestyle everyone is looking for: easy living, a sought-after location, and true indoor-outdoor charm. Set on the second floor, the condo features two private balconies, one in front and one in back, perfect for enjoying tropical breezes, morning coffee, or a quiet moment after a day downtown. Inside, the open living area flows comfortably into a modern kitchen, creating an inviting space for relaxing or entertaining. A uniquely spacious bathroom, rarely found in Shipyard condos, adds extra comfort and practicality. Offered fully furnished, this home is move-in ready and well positioned for personal use or rental income. The lushly landscaped Shipyard community offers a pool, winding paths, and a peaceful setting just moments from Fort Zachary Taylor State Park, the waterfront, Truman Annex, and the restaurants, galleries, and energy of Duval Street. Whether you are looking for a Key West getaway, full-time island home, or investment property, this condo delivers location, lifestyle, and ease in one of Old Town's most desirable communities.

204 Southard St Unit 5, Key West

2 Beds ⋅ 1 Baths ⋅ 620043 MLS

Located in the desirable Truman Annex Shipyard community, this beautifully updated first-floor condominium offers 2 bedrooms, 1 bath. The newly renovated kitchen features stainless steel appliances, granite countertops, and modern finishes, while the updated bath includes a stylish walk-in shower. A redesigned laundry area includes a new washer and dryer for added convenience. Step outside to the spacious rear deck, perfect for outdoor dining and relaxing, with easy access to the nearby community pool. Additional highlights include impact windows, French doors, and an assigned parking space located just steps from the front entrance. Whether you're seeking a full-time residence, vacation getaway, or income-producing property, this Shipyard condo offers an exceptional opportunity in one of Key West's most sought-after communities.

620 Thomas St Unit 186, Key West

S.T.S. Food Truck (Sliders, Tacos & Sammies) is ready to roll and start serving. This is a 2014 Dodge Ram 2500 ProMaster food van with only 50,000 miles. This is a true turnkey-style setup for operators who want a clean, capable build-out and the flexibility only a van can offer--drive in, serve, and roll out with ease for private events, weddings, catering, and high-traffic venues. Included equipment: A/C, Awning, (2) propane tanks, generator, refrigerator, prep station coolers, stovetop, flat-grill, BBQ smoker, food warmer, steam table, exhaust hood & fan, worktable, hot water heater, hand-wash sink, triple sink, fresh & gray water tanks, fire extinguishers, and a professional fire suppression system. Everything is up to code. Operating history includes major success at farmers markets from Key West to Sugarloaf to Big Pine, plus concerts and special catering events. Sale includes food van and all tangible equipment only. Licenses and permits are non-transferable; however, are easily obtained and at a reasonable cost. No outstanding debts. Seller is exiting due to time constraints. Equipment may be removed if you want a custom reconfiguration.

Duval St Unit Food Truck, Key West

2 Beds ⋅ 2 Baths ⋅ 619263 MLS

HARBOUR PLACE | TRUMAN ANNEX. This waterfront gated community boasts amazing ocean views from the pool and patio areas. Unit 102 has an open floor plan that seamlessly connects the dining and living areas, leading out to a private balcony. This residence features two bedrooms, including a spacious primary suite with a large walk-in closet and a full bathroom. The second bedroom is also generous in size and offers plenty of closet space. As a first-floor unit, it provides easy accessibility without the need for elevators or stairs. Additionally, this unit comes equipped with a washer and dryer, along with a covered parking space. Features include central air conditioning, impact windows and doors, and it comes furnished. Harbour Place provides secure entry and a heated pool amidst beautifully landscaped grounds, all just steps away from Duval Street, shopping, theaters, Fort Zachary Beach, and the Amphitheater.

115 Front St Unit APT 102, Key West

2 Beds ⋅ 3 Baths ⋅ 619140 MLS

President's Walk townhome in the Truman Annex. This is a two-bedroom, 2.5-bathroom unit that also includes a deeded carport. It is a great location close to the community pool and all the downtown attractions that Key West has to offer. It features an open floor plan with kitchen, half bath, dining and living areas that open to the rear and side yard! Upstairs are two-bedroom ensuites with vaulted ceilings and each with their own private bath and porches. The windows and doors are combination of wood and impact. It has a non-transient rental license that allows monthly or longer rentals.

564 Porter Ln, Key West

2 Beds ⋅ 2 Baths ⋅ 618955 MLS

Beautifully updated and styled with plush new interior designed furnishings, 401 Emma Street Unit H is a vacation rental townhome that has BOTH Ocean and Harbor views in the heart of Truman Annex. Enjoy gorgeous sunset vistas of the Atlantic and the Gulf while also overlooking the the tropical and lush grounds of Truman Waterfront Park and Truman Harbor. This residence features a large covered balcony right off the main living area with living room, dining room and kitchen all in easy access. The second story's primary bedroom and bath opens out to its own private balcony. This gem is in the highly desirable Old Town location Mill's Place condominiums in Truman Annex.

401 Emma St Unit APT H, Key West

3 Beds ⋅ 3 Baths ⋅ 617136 MLS

103 Front Street is a one of a kind masterpiece of architectural design and modern aesthetic. Built in the early 1900s, this imposing structure has been thouroughly restored and updated into a stunning home. The interior features a large great room with soaring ceilings, custom beams and woodwork. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic staircase leads to a second floor walkway which is open to the main level. The floor plan provides privacy for each bedroom with the primary suite at one end of the hallway and a guest bedroom suite at the other end. Another guest bedroom and bath are on the first floor creating an option for a first floor primary bedroom. Custom features throughout are evidence of the artistic ingenuity used in the design of this impressive home. The kitchen features custom wood cabinets and granite countertops and is open to the dining area. Tall windows and french doors flood the home with sunlight. This home is perfect for indoor/outdoor entertaining. A wet bar features custom built ins plus an icemaker and refrigerator. Fronted by a white picket fence, the home sits back from the street and is adorned by tropical foliage. This unique structure with thick brick walls and impressivly tall windows offers passers by a glimpse of the historic origins of the Truman Annex. Its location in the heart of old town Key West provides easy walkability to the waterfront promenade, Ft. Taylor beach, cultural venues, shops and restaurants. The property comprises two lots with a large swimming pool and spa plus an outdoor shower between the covered and open air loggia and parking. There's plenty of space for entertaining outdoors under the palm trees. This estate home is one of a kind was restored to the highest standards. One must see this home to appreciate the incredible design and attention to detail that went into this historic treasure.

103 Front St, Key West

3 Beds ⋅ 3 Baths ⋅ 616322 MLS

Prior to the development of Truman Annex which was a notable Naval base located in the center of Key West, now has many upscale homes and condos. This newly renovated 3-bedroom, 3-bathroom residence blends historic charm with cutting-edge contemporary design by interior designer David Smith. Step inside to soaring open ceilings with exposed ductwork and striking geometric lighting. Smart home technology is seamlessly integrated, allowing you to control the entire residence from your iPhone or iPad. Blackout and privacy illusion shades are installed throughout with impact windows and doors. The chef's kitchen is a true showpiece, featuring illuminated crystalline quartz countertops, an oversized island with under-counter lighting, and premium Miele appliances. A sleek induction cooktop with downdraft ventilation, walnut cabinetry with custom divider drawers, and 48'' x 48'' high-grade porcelain tile flooring complete the space. The primary suite offers ,a dramatic down-lit interlocking panel accent wall, a custom walk-in closet, and views of the historic Little White House. Spa-inspired bathrooms showcase porcelain walls, quartz sinks, smart toilets, and multi-head showers. The second en-suite bedroom features a private terrace, illuminated niche, and a luxurious walk-in shower. Every closet in the home is custom-designed and thoughtfully lit. Additional highlights include a fully furnished turnkey offering, oversized 8' doors, recessed window trims and baseboards, a large community pool, and one covered deeded parking space.

115 Front St Unit 101, Key West

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