14

Truman Annex Homes for Sale

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  • /44

    $6,850,000

    • 3 Beds
    • 3 Baths
    • 4,200 Sq Ft

    103 Front St, Key West, FL 33040

    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. A dramatic staircase leads to a second floor walkway which is open to the main level. On one end is

    Laura McChesney Preferred Properties (KW)

    103 Front St, Key West, FL 33040
  • /22

    $1,596,000

    • 2 Beds
    • 2 Baths
    • 1,002 Sq Ft

    404 Porter Ln Unit 16, Key West, FL 33040

    404 Porter Lane is located in the sought after Porter Court community where properties rarely come on the market. Duval, shops and restaurants are only a short stroll away. This corner unit is flooded with natural light from windows on three sides. It features private front and rear porches plus a separate gate to the deeded parking. A cathedral ceiling and tall windows in the living room opens

    Laura McChesney Preferred Properties (KW)

    404 Porter Ln Unit 16, Key West, FL 33040
  • /53

    $2,795,000

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft

    502 Porter Ln, Key West, FL 33040

    One of the largest townhomes available in Truman Annex, plus your own private pool. The first floor includes a dining area, kitchen, bathroom and a guest bedroom or den with a convenient murphy bed. The living room opens to the rear deck and pool. Upstairs is the Primary bedroom ensuite with a private deck. Two more guest bedrooms share a bath and a covered porch that overlooks Porter Lane.

    The Behmke Group Keller Williams Key West Compass Realty

    502 Porter Ln, Key West, FL 33040
  • /49

    $1,875,000 Open Sat 12PM - 2PM

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

    101 Front St Unit 23, Key West, FL 33040

    Completely renovated and move-in ready, The Foundry #23 in Key West's exclusive Truman Annex is a rare gem that blends historic charm with modern luxury. This beautifully updated townhome features custom Hansen & Bringle cabinetry throughout, quartz countertops, and brand-new appliances in the kitchen. The Primary Suite offers ample closet space and a redesigned bath with custom cabinetry and a

    Loren Rea Truman & Co. (KW)

    101 Front St Unit 23, Key West, FL 33040
  • /64

    $1,950,000

    • 2 Beds
    • 3 Baths
    • 1,418 Sq Ft

    413 Emma St Unit A, Key West, FL 33040

    Welcome to 413 Emma Street, Unit A - a rare opportunity to own a piece of Key West history in the prestigious Truman Annex. This elegant two-story, 2-bedroom, 2.5-bath villa is located in the exclusive Mills Place Condominiums, a unique enclave of just 20 residences, thoughtfully designed within charming bungalows and the original 1844 hospital by architect Robert Mills. This beautifully

    Jaime Caballero Key West Vacation Properties & Realty, LLC (KW)

    413 Emma St Unit A, Key West, FL 33040
  • /54

    $2,999,500

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

    401 Emma St Unit H, Key West, FL 33040

    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

    Ralph Sanchez Century 21 All Keys Inc (KW)

    401 Emma St Unit H, Key West, FL 33040
  • /35

    $849,000

    • 2 Beds
    • 1 Bath
    • 646 Sq Ft

    620 Thomas St Unit 268, Key West, FL 33040

    Shipyard Condominiums are in the Truman Annex Complex which is located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also located 1/4 mile from one of the best beaches on the island. This two-bedroom, one bath gem is conveniently located and overlooking the Truman Waterfront Park and walking paths. Recently updated with new furniture this a perfect place

    The Behmke Group Keller Williams Key West Compass Realty

    620 Thomas St Unit 268, Key West, FL 33040
  • /28

    $869,000

    • 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
  • /18

    $2,200,000

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

    105 Front St Unit 119, Key West, FL 33040

    SOLD TURN KEY! This beautiful two bedroom, 2.5 bath Harbour Place condominium is located on the desirable first level with one of the largest decks which includes plenty of room for entertaining, relaxing and watching the sunsets and boats coming in out of the Key West harbor. There are gorgeous views of the open water from the living and dining rooms as well as the kitchen. The spacious bedrooms

    The Behmke Group Keller Williams Key West Compass Realty

    105 Front St Unit 119, Key West, FL 33040
  • /46

    $2,975,000 Open Sun 11AM - 1PM

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

    102 Admirals Ln, Key West, FL 33040

    The ultimate lock-and-leave Key West retreat awaits in the heart of Old Town! Perfect for those seeking a low-maintenance getaway this residence offers effortless luxury living and the convenience of a fly-in, fly-out lifestyle.Located on exclusive Admirals Lane within the award-winning TRUMAN ANNEX, this is the LARGEST townhouse in the annex. The home features soaring 10-foot ceilings on all

    Lisa Swanson The Agency Florida Keys

    102 Admirals Ln, Key West, FL 33040
  • /18

    $1,395,000

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

    101 Front St Unit 8, Key West, FL 33040

    This beautifully updated Foundry townhome in the exclusive gated Truman Annex community is a dream come true! The floor to ceiling windows and doors at the entry allow sunshine to filter into the main floor living space creating a bright and airy space. The main floor has 11 foot ceilings and double French doors that open to the private front courtyard and porch. The open floor plan allows for an

    Shannon Maska Last Key Realty, Inc (KW)

    101 Front St Unit 8, Key West, FL 33040
  • /57

    $4,350,000

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

    202 Admirals Ln, Key West, FL 33040

    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 vacationers alike. Situated nearby the iconic Duval Street

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

    202 Admirals Ln, Key West, FL 33040
  • /56

    $3,600,000

    • 4 Beds
    • 3 Baths
    • 1,920 Sq Ft

    514 Emma St, Key West, FL 33040

    514 Emma is a wonderful single-family home located in Truman Annex. The first floor features a large, updated chef's kitchen with double wall ovens, double refrigerator/freezers and a large island. There is a guest bedroom, and a full bathroom as well as a dining area. French doors in the living area, open to the large rear porch and pool. There is a carport on the rear of the property, PLUS a

    The Behmke Group Keller Williams Key West Compass Realty

    514 Emma St, Key West, FL 33040
  • /27

    $2,250,000

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

    115 Front St Unit 101, Key West, FL 33040

    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

    Key West Luxury Finders Preferred Properties (KW)

    115 Front St Unit 101, Key West, FL 33040

Why Live in 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%, your estimated principal and interest payment would be $7,190 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $308K a year to afford the median home price in Truman Annex. Learn how much home you can afford with our Home Affordability Calculator. 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.
Are home prices dropping in Truman Annex?
Yes, home prices in Truman Annex are down 5% in the last 12 months.

Home Trends in Truman Annex, FL

Housing Trends

Median Sale Price
$1,160,000
Median Single Family Sale Price
$1,850,000
Median 2 Bedroom Sale Price
$1,225,000
Median 1 Bedroom Sale Price
$675,000
Average Price Per Sq Ft
$1,369
Number of Homes for Sale
14
Last 12 months Home Sales
23
Months of Supply
7.30
Median List Price
$1,500,000
Median Change From 1st List Price
9%
Median Home Sale Price YoY Change
-16%
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