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 ⋅ 1 Baths ⋅ 601075 MLS

Picture perfect condo on the quiet back row of Shipyard awaits you. This downstairs 2 bedroom/ 1 bathroom unit has everything you need. Nicely renovated and decorated, it has a wonderful back deck for morning coffee or a late day cold beverage. Just outside your back deck is the Truman Waterfront Park and Ft Zachary Taylor state park. Only a couple of blocks will find you on Duval St with all the shops, restaurants and bars. This is such a nice getaway place as well as a very attractive vacation rental. Make it your ''Piece of Paradise''

620 Thomas Unit 174, Key West

Listing courtesy of Keller Williams Key West Compass Realty.

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

Listing courtesy of Key West Vacation Properties & Realty, Llc (Kw).

2 Beds ⋅ 2 Baths ⋅ 600988 MLS

Opportunity to purchase a pristine Presidents Walk townhouse in Truman Annex complete with special transient rental privileges. Updates galore in this turnkey gem to include remodeled kitchen and bathrooms, impact doors and windows, on demand water heater, full capacity washer/dryer 2021, central a/c 2021, built in entertainment center, turnkey furnished with quality furnishings and tasteful tropical decor, plantation shutters and more! Deeded carport with storage conveniently located immediately out back gate. Professionally managed with bookings to convey.

530 Porter, Key West

Listing courtesy of Truman & Co. (Kw).

2 Beds ⋅ 2 Baths ⋅ 600943 MLS

A Perfect spot to own a ''piece of Paradise'', this upstairs 2 bedroom/2 bathroom end unit Shipyard condo checks off all the boxes. There's plenty of room with vaulted ceilings in the living and kitchen area and both bedrooms and the primary bedroom has the bathroom ensuite. A big plus for this unit is an excellent rental history should you wish to enjoy your place and rent it when you're not staying there. Perfectly located, it is just two blocks to Duval St and a short walk or bike ride to Truman Waterfront and Ft Zachary Taylor state beach.

620 Thomas Unit 277, Key West

Listing courtesy of Keller Williams Key West Compass Realty.

4 Baths ⋅ 600635 MLS

Now available is a majority interest in the Courthouse Business Center. Offered are 14 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. - 203sq.ft., total 2080sq.ft. Units can be purchased individually.

300-302 Southard Unit 14 Units for Sale, Key West

Listing courtesy of Berkshire Hathaway Knight & Gardner Realty.

2 Beds ⋅ 3 Baths ⋅ 600346 MLS

Perfect location in Key West! Excited to announce a rare Porter Court townhome offered for sale. A complete photo package, 3D virtual tour, and floor plan are on the way, but the property is available now for your showings and purchase while prepared for sale. The home features 2 bedrooms and 2.5 baths on 2 floors with a stylish contemporary kitchen and 2 suites featuring absolutely gorgeous bathrooms. Extending the main living area is a bricked patio with a high privacy fence, while a bedroom has a cozy balcony to enjoy the sound of palms rustling in the breeze. Providing ultimate convenience in the heart of Old Town, Porter Court is an intimate gated enclave located within Truman Annex. There's even an owner's pedestrian gate leading you to a 2 block causal stroll to Duval Street. Only steps from your front door is an inviting swimming pool, hot tub, and sunning area. Your assigned parking spot is comfortably close to your front step. Windows have been installed with impact glass, while doors are in the process of being replaced. An entire furniture package is included the sale. Although the home is owner occupied and not currently a rental, lucrative monthly vacation rental income is estimated as much as $15,000. Sunsets at Mallory Square, famous Duval St. nightlife, the beach and new concert venue featuring top billed music acts are nearby in every direction. Please provide for seller continued occupancy until 5/31/22 or a closing on that date in your purchase offer.

417 Porter, Key West

Listing courtesy of Coldwell Banker Schmitt Real Estate Co. (Kw).

4 Beds ⋅ 5 Baths ⋅ 599229 MLS

Currently on The National Register of Historic Places, The James J. Curtis House c. 1874 was acquired by the Navy in 1903. Extensive work was performed on the home which included adding the three bay porches up and down, installing the hip roof to replace the flat roof and raising the home with the installation of 18 concrete piers to stabilize the foundation. The Navy was instrumental in establishing other homes in the Whitehead/Caroline street corridor which became officers quarters for the various branches that existed . The Curtis house is the ONLY home that exists in its original location. Listed in the Historically Significant Building Analysis performed by the Navy, the home became The Marine Officers Quarters as M2 The home is representative of a late nineteenth century vernacular know as a ''Conch House'', free of gingerbread, simple in its design, shingle roofing, weathered siding with louvered shutters. Two stories with balustrade railings and 9/9 window styles. As it exist today its one of the finest examples of ''Conch House'' Architecture in Key West. Additional information will be provided in a addendum to cover all the upgrades and enhancement performed on the home. The list is detailed and extensive.

330 Caroline, Key West

Listing courtesy of Keller Williams Key West Compass Realty.

1 Beds ⋅ 1 Baths ⋅ 599037 MLS

This second floor Shipyard Condo has been recently updated. New flooring, and shiplap wall in dining area. New kitchen quartz countertop, backsplash, sink and stainless-steel appliances. Bosch dishwasher, induction range and SMEG coffee maker. New West Elm chandeliers and kitchen lighting. New ceiling fans and bathroom vanity. New bed, mattress, custom nightstands, living and dining furniture. Added owner's closet. Recently painted interior. Large rear deck offers plenty of room for relaxing, entertaining, and dining with new patio furniture and rugs. Property includes the special Truman Annex transient rental license. Great location one building off Southard Street. Buyer must honor future rentals. Property must close after April 9, 2022.

106 Southard Unit 2, Key West

Listing courtesy of Keller Williams Key West Compass Realty.

3 Beds ⋅ 3 Baths ⋅ 598752 MLS

Known as Building #11, this extraordinary property built in 1918, is the historic site of the 'Machine Shop' in the heart of the award-winning gated community of the Truman Annex. This rare opportunity has been expertly restored featuring dramatic voluminous ceilings, soaring interior brick walls and massive wooden beams making it a perfect blend of historic renovation and modern additions on a spectacular oversized lot. Five large arched French doors open across the front overlooking the gorgeous tropical landscape. The main level features sweeping travertine floors with master craftsman built-ins, a handsome great room which includes a separate bar, a gourmet kitchen, an elegant dining area and additional living room. There is also a guest suite on the first floor which opens out to the pool, waterfall, and stone deck.The amazing second level features the primary and guest suites separated by a breathtaking gallery bridge with privacy doors for each bedroom. Both wings include beautiful built-ins, hardwood flooring, custom lighting and luxurious bathrooms with plenty of upgrades.This home has been maintained meticulously and only a handful of personal guests have enjoyed its wonderful architectural work of art.The oversized carport includes the 'boathouse' (an ample storage area within the carport) which was newly built to match the original architectural style.This gem is nestled between its neighbors of Truman's Little White House and The Foundry building making it one of the most sought after locations in the Florida Keys.

103 Front, Key West

Listing courtesy of Keller Williams Key West Compass Realty.