8

Truman Annex Condos for Sale

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  • /27

    $2,350,000

    • 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
  • /65

    $2,700,000

    • 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
  • /16

    $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

    The Behmke Group Keller Williams Key West Compass Realty

    105 Front St Unit 119, Key West, FL 33040
  • /36

    $879,000

    • 2 Beds
    • 1 Bath
    • 646 Sq Ft

    620 Thomas St Unit 176, Key West, FL 33040

    Ground floor end unit! Two-bedroom, one bath Shipyard condo. Updated kitchen with stainless steel appliances. Updated bath with shower. New impact windows and doors. The Shipyard is in the Truman Annex in Old Town Key West. Great location with easy walking and biking to all the action and great restaurants, beaches and sunsets that Key West offers.

    The Behmke Group Keller Williams Key West Compass Realty

    620 Thomas St Unit 176, Key West, FL 33040
  • /42

    $2,400,000

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

    107 Front St Unit 215, Key West, FL 33040

    Second floor Harbour Place condominium features 2 bedrooms and 2.5 baths. Relax on your private balcony and admire the beautiful sunsets and views of the ocean, gulf and all the activity in Key West harbor. Recently updated, this beautiful property is move-in ready and has spectacular views from the large windows and both bedrooms. Easily accessible by the conveniently located elevator. One of

    The Behmke Group Keller Williams Key West Compass Realty

    107 Front St Unit 215, Key West, FL 33040
  • /16

    $699,000

    • 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!*Newly installed impact windows as of June 2025!

    Robert Donahue Key West Luxury Real Estate Inc (KW)

    620 Thomas St Unit 152, 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
  • /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

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.

Home Trends in Truman Annex, FL

Housing Trends

Median Sale Price
$1,225,000
Median Single Family Sale Price
$1,825,000
Median 2 Bedroom Sale Price
$879,000
Median 1 Bedroom Sale Price
$675,000
Average Price Per Sq Ft
$1,424
Number of Homes for Sale
18
Last 12 months Home Sales
33
Months of Supply
6.50
Median List Price
$1,462,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-6%
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