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Truman Annex Homes for Sale

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  • /72

    $3,395,000

    • 4 Beds
    • 4 Baths
    • 2,488 Sq Ft

    102 Admirals Ln, Key West, FL 33040

    Exquisite Key West Retreat in Truman Annex! Experience the best of Key West with this luxurious retreat in the exclusive gated community of Truman Annex. This Caribbean and British Colonial-inspired home blends sophistication and comfort, making it ideal as an upscale vacation home or investment with rental potential. The transient license allows weekly rentals. The residence spans three levels

    Agent Photo

    Lisa Swanson

    Berkshire Hathaway HomeServices Knight & Gardner Realty

    (786) 869-4388

    102 Admirals Ln, Key West, FL 33040
  • /44

    $2,095,000

    • 2 Beds
    • 3 Baths
    • 1,312 Sq Ft

    216 Fleming St, Key West, FL 33040

    Located in the prestigious gated Truman Annex, this beautifully appointed 2-bedroom, 2.5-bath home offers refined coastal living just steps from Duval Street and Truman Waterfront. Thoughtfully designed with elegant finishes and an open, airy layout, this residence is perfect for those seeking a private sanctuary in Old Town.A private entrance welcomes you into a turn-key interior, where Serena &

    Agent Photo

    Brenda Donnelly

    Brenda Donnelly Real Estate LLC

    (786) 733-5614

    216 Fleming St, Key West, FL 33040
  • /45

    $1,495,000

    • 2 Beds
    • 3 Baths
    • 1,260 Sq Ft

    115 Front St Unit 202, Key West, FL 33040

    Second Floor Harbour Place Condo located in the historic Navy Administrative Building. Features high ceilings and tile floors throughout. One level living with 2 bedrooms and 2.5 Baths. Large primary bedroom ensuite with walk-in closet. The guest bedroom has French doors that open to the balcony with guest bathroom in the hall. Includes the special Truman Annex transient rental license.

    The Behmke Group Keller Williams Key West Compass Realty

    115 Front St Unit 202, Key West, FL 33040
  • /3

    $2,425,000

    • 2 Beds
    • 3 Baths
    • 1,620 Sq Ft

    106 Admirals Ln, Key West, FL 33040

    Updated photos coming soon. This town house is in the award-winning Truman Annex and is located on a private lane surrounded by charming custom-built homes. The generous open floor plan features 10-foot ceilings both on the first and second levels with hardwood floors and crown molding. Enjoy the theater style kitchen with quartz countertops and stainless-steel appliances with a gas cook top. The

    The Behmke Group Keller Williams Key West Compass Realty

    106 Admirals Ln, Key West, FL 33040
  • /16

    $815,000

    • 2 Beds
    • 1 Bath
    • 604 Sq Ft

    620 Thomas St Unit 152, Key West, FL 33040

    This ground floor unit in the beautiful and gated Truman annex has been an extremely successful vacation rental for the past 11 years. It comes as no surprise that it has gained rave reviews and repeat guests over the years who delight in the ideal location, functionality, beautiful grounds , amazing pool and privacy!

    Robert Donahue Key West Luxury Real Estate Inc (KW)

    620 Thomas St Unit 152, Key West, FL 33040
  • /28

    $899,000

    • 2 Beds
    • 1 Bath
    • 646 Sq Ft

    204 Southard St Unit 5, Key West, FL 33040

    Welcome to your perfect island retreat! This beautifully maintained 2-bedroom, 1-bathroom condo is ideally situated on the second floor, offering the best of Key West living. Step out onto one of the two private balconies--one in the front and one in the rear--which are perfect for enjoying the ocean breeze and tropical treetop views.Inside, you'll find an inviting layout, featuring a modern

    Stacy Stahl Realty ONE Group Destination

    204 Southard St Unit 5, Key West, FL 33040
  • /24

    $930,000

    • 2 Beds
    • 1 Bath
    • 646 Sq Ft

    620 Thomas St Unit 157, Key West, FL 33040

    MUST SEE!! Recently renovated, ground level Shipyard condo with view of pool from front deck & living room. Hurricane rated doors and windows. Floorplan changed to enter directly into the living room, Condo offers a spacious custom kitchen with stainless appliances. Beautifully tiled bathroom with glass enclosed shower. Laundry closet, both Bedrooms open out to the private rear deck, Luxury

    Bud Adorjan TALL PINES REALTY

    620 Thomas St Unit 157, Key West, FL 33040
  • /48

    $2,495,000

    • 2 Beds
    • 3 Baths
    • 1,350 Sq Ft

    105 Front St Unit 121, Key West, FL 33040

    Epitome of Paradise!There is an enveloping comfort, an ease and repose, that beckons one away from the world's cares and invites one to lounge, drift away, and dream in this gorgeous waterfront condominium.Enjoy a single level open floor plan with two bedrooms, two full baths and a convenient powder room.Exquisitely decorated to reflect the local island flavor with all new furniture and

    The Behmke Group Keller Williams Key West Compass Realty

    105 Front St Unit 121, Key West, FL 33040
  • /32

    $1,275,000

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    237 Southard St, Key West, FL 33040

    This beautifully renovated and furnished end unit townhouse in the award winning Truman Annex is now for sale. This 2 story 2 bedroom/ 1 1/2 bath townhouse has a wonderfully renovated kitchen with quartz countertops, new cabinets and stainless appliances. The dining and living area flow outside to a poolside deck area. The front porch is wonderful for people watching and a great spot for the

    Mike Caron Keller Williams Key West Compass Realty

    237 Southard St, Key West, FL 33040
  • /28

    $675,000

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft

    210 Southard St Unit 2, Key West, FL 33040

    WELCOME TO THE MOST UNIQUE ISLAND IN FLORIDA! Set in the most desirable Gated Community only 2 blocks to Duval St. You will love the walkability here, close to all amenities. You can walk or ride your bike to Fort Zachary and spend the day on the beach. Your 2nd Floor Condo offers Brand New Hurricane Windows 2024 ($20,000 upgrade), Beautiful Luxury Vinyl Flooring throughout, Tiled Bath, Solid

    Stephen Hachey

    210 Southard St Unit 2, Key West, FL 33040
  • /49

    $1,975,000 Open Fri 11AM - 1PM

    • 2 Beds
    • 3 Baths
    • 1,216 Sq Ft

    101 Front St Unit 23, Key West, FL 33040

    The Foundry #23 in Key West's exclusive Truman Annex is a rare masterpiece, blending history, modern luxury, and high-end craftsmanship. This beautifully renovated townhome offers the ultimate in island living.Exceptional Upgrades: Every detail has been thoughtfully updated. The kitchen features custom cabinetry from Hansen & Bringle, paired with sleek quartz countertops and brand-new appliances.

    Loren Rea Truman & Co. (KW)

    101 Front St Unit 23, Key West, FL 33040
  • /52

    $2,495,000

    • 3 Beds
    • 3 Baths
    • 1,325 Sq Ft

    115 Front St Unit 101, Key West, FL 33040

    Step into a piece of history, reimagined for modern luxury. This stunning 3-bedroom, 3-bath condominium is located in the historic Naval Administration Building within the prestigious, award-winning Truman Annex. Completely renovated to the highest contemporary standards, this one-of-a-kind residence boasts soaring exposed beam ceilings, ultra-thick concrete walls and ceilings for unparalleled

    Jimmy Lane Island Life Realty Experts

    115 Front St Unit 101, Key West, FL 33040
  • /42

    $2,999,500

    • 2 Beds
    • 2 Baths
    • 1,770 Sq Ft

    401 Emma St Unit H, Key West, FL 33040

    Vacation rental Ocean and Harbor view unit in Truman Annex. Beautiful 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. The second story's primary bedroom and bath opens out to

    Ralph Sanchez Century 21 All Keys Inc (KW)

    401 Emma St Unit H, Key West, FL 33040
  • /26

    $870,000

    • 2 Beds
    • 1 Bath
    • 604 Sq Ft

    620 Thomas St Unit 190, Key West, FL 33040

    Tropical Paradise Living in the Heart of Old Town, Key West.Discover your dream retreat with this beautifully updated 2-bedroom, 1-bath condo, perfectly situated in the exclusive Truman Annex. Just 2 short blocks from Duval Street.Step inside to a renovated kitchen featuring stunning marble countertops, stainless steel appliances & elegant wood cabinets--perfect for entertaining or enjoying quiet

    Paige Bethel Island Home Realty Inc.

    620 Thomas St Unit 190, Key West, FL 33040
  • /40

    $2,949,000

    • 3 Beds
    • 3 Baths
    • 1,426 Sq Ft

    100 Admirals Ln, Key West, FL 33040

    Discover your dream home at the prestigious Truman Annex Community, situated on the serene Admirals Lane. This two-story detached single-family residence offers a perfect blend of comfort and elegance with 3 bedrooms and 3 full bathrooms. Enhanced by impact windows and doors, the house also features a private carport for added convenience. Adjacent to the property lies a shared community pool,

    Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty

    100 Admirals Ln, Key West, FL 33040
  • /60

    $4,850,000

    • 5 Beds
    • 4 Baths
    • 3,148 Sq Ft

    202 Admirals Ln, Key West, FL 33040

    Investment opportunity! Weekly rentals are allowed! Nestled within the highly sought-after Truman Annex in Old Town Key West, 202 Admirals Lane exudes coastal charm and luxury living at its finest. Boasting 5 bedrooms and 4 full bathrooms, this meticulously maintained residence showcases beautifully renovated bathrooms and a private pool oasis, offering an idyllic retreat for residents and

    Tom Mclaughlin Coldwell Banker Schmitt Real Estate Co. (KW)

    202 Admirals Ln, Key West, FL 33040
  • /35

    $1,399,000

    • 2 Beds
    • 3 Baths
    • 960 Sq Ft

    231 Southard St, Key West, FL 33040

    For the first time, the Key West home of famed landscape architect and Martha Stewart co-star Fernando Wong is available. Welcome to your dream townhouse nestled in the heart of the exclusive Truman Annex, just steps away from the restaurants, shops and bars on Duval Street. This professionally decorated 2-bedroom, 2.5-bathroom townhouse offers the perfect blend of modern comfort and island

    Carrie Howe Keller Williams Key West Compass Realty

    231 Southard St, Key West, FL 33040
  • /29

    $1,295,000

    • 2 Beds
    • 3 Baths
    • 960 Sq Ft

    208 Fleming St, Key West, FL 33040

    Owner is a licensed real estate agent and listing agent.Charming End Unit Townhome in the Heart of Truman Annex, Key WestNestled in the highly sought-after Truman Annex, this exceptional end unit townhome offers the perfect blend of privacy, luxury, and tropical living. Boasting an unbeatable location just steps from the vibrant attractions of Old Town Key West and the serene beauty of Fort

    Tracy Dubensky Real Estate Management of Key West, LLC

    208 Fleming St, Key West, FL 33040
  • /28

    $1,325,000 Open Fri 10AM - 12PM

    • 2 Beds
    • 3 Baths
    • 1,216 Sq Ft

    101 Front St Unit 15, Key West, FL 33040

    Located in the prestigious Truman Annex community, this town home in The Foundry is the perfect getaway offering the perfect blend of luxury, comfort, and convenience. This beautifully designed 2-bedroom, 2.5-bathroom home enjoys a highly desirable location with easy access to Key West's vibrant Old Town, while maintaining privacy and security within a gated community.As you step inside the

    Bobby Krug Ocean Sotheby's International Realty

    101 Front St Unit 15, Key West, FL 33040
  • /77

    $6,995,000

    • 5 Beds
    • 4 Baths
    • 3,173 Sq Ft

    101 Admirals Ln, Key West, FL 33040

    With its special transient license, The Royal Compound is currently generating $500,000 a year from first-class guests who will accept only the best in vacation homes. What's interesting is that most of the rental income comes from monthly rentals, so you can expect almost as much income without a transient license. This extraordinary home is situated on one of the largest lots (14,183 SF) in

    Andrea Otava Last Key Realty, Inc (KW)

    101 Admirals Ln, Key West, FL 33040
  • /39

    $2,200,000

    • 2 Beds
    • 3 Baths
    • 1,210 Sq Ft

    105 Front St Unit 119, Key West, FL 33040

    SOLD TURN KEY! This 2 bedroom, 2.5 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 plenty of room for entertaining, relaxing and watching the sunsets and boats coming in out of the Key West harbor. The elevator is conveniently located, and the community pool is steps away. Covered parking.

    The Behmke Group Keller Williams Key West Compass Realty

    105 Front St Unit 119, Key West, FL 33040
  • /40

    $859,000

    • 2 Beds
    • 1 Bath
    • 646 Sq Ft

    620 Thomas St Unit 284, Key West, FL 33040

    SOLD TURN KEY! 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 other recent updates make this move-in ready. Impact French Doors open to the rear deck that offers a tree top view and has a glimpse of the community pool. There is another deck off the kitchen to enjoy the

    The Behmke Group Keller Williams Key West Compass Realty

    620 Thomas St Unit 284, Key West, FL 33040

About Truman Annex

Truman Annex in Key West offers a diverse range of housing options, from classic Southern Cottage-style row homes to grand Italian Revival residences, all unified by their white exteriors. The neighborhood includes multi-unit properties like The Foundry’s townhouses and Harbour Place condos, which repurposed former military buildings. Amenities such as a large community pool at Shipyard Condos and private courtyards at President’s Walk townhouses enhance the living experience. Many properties allow for weekly and monthly rentals, appealing to seasonal residents. The area is safer than the national average, providing a secure environment for families and individuals alike. Truman Annex is within walking distance of Duval Street, known for its vibrant bars, restaurants, and shops. Popular spots include Hog’s Breath Saloon, Sloppy Joe’s, and the Green Parrot, which hosts live music regularly. Dining options extend beyond Duval Street with establishments like Blue Heaven and El Meson de Pepe. For groceries, Fausto’s Food Palace and national chains like Publix and Winn-Dixie are about 3 miles away in New Town. Cultural attractions near Truman Annex include the Custom House Museum, the Waterfront Playhouse, and the Key West Aquarium. The neighborhood also hosts various events throughout the year, such as Hemingway Days and the Key West Songwriters Festival. Educational options are strong, with highly rated schools like Sigsbee Charter School and Key West High School serving the area. Truman Waterfront Park and Fort Zachary Taylor Historic State Park offer recreational opportunities, including playgrounds, trails, and popular beaches for swimming and snorkeling.

Frequently Asked Questions

Is Truman Annex a good place to live?
Truman Annex is a good place to live. Truman Annex is considered very walkable and very bikeable with some transit options. Truman Annex has 2 parks for recreational activities. It is somewhat dense in population with 10.3 people per acre and a median age of 58. The average household income is $149,868 which is above the national average. College graduates make up 73.2% of residents. A majority of residents in Truman Annex are home owners, with 48% of residents renting and 52% of residents owning their home. A local real estate agent serving Truman Annex can help you decide if this neighborhood is the right one for you. Learn more on our Truman Annex neighborhood guide.
Is Truman Annex, FL a safe neighborhood?
Truman Annex, FL is less safe than the average neighborhood in the United States. It received a crime score of 5 out of 10.
How much do you need to make to afford a house in Truman Annex?
The median home price in Truman Annex is $1,500,000. If you put a 20% down payment of $300,000 and had a 30-year fixed mortgage with an interest rate of 6.83%, your estimated principal and interest payment would be $7,850 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $336K a year to afford the median home price in Truman Annex. The average household income in Truman Annex is $150K.
What are the best public schools in Truman Annex?
The best public schools that serve Truman Annex are:
What are the best private schools in Truman Annex?
The best private schools that serve Truman Annex are:
What are the most popular zip codes in Truman Annex, Key West, FL?
The most popular zip codes in Truman Annex, Key West, FL include 33040 and 33042.
What are the most popular neighborhoods near Truman Annex, Key West, FL?
The most popular neighborhoods near Truman Annex, Key West, FL are Old Town, Casa Marina, The Meadows, Mid Town and New Town.

Home Trends in Truman Annex, FL

Home Trends

Median Price (12 Mo)
$1,437,500
Median Single Family Price
$2,095,000
Median Townhouse Price
$1,350,000
Median 2 Bedroom Price
$880,000
Median 1 Bedroom Price
$675,000
Average Price Per Sq Ft
$1,489
Number of Homes for Sale
20
Last 12 months Home Sales
44
Months of Supply
5.50
Median List Price
$1,500,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
15%
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