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Truman Annex Homes for Sale

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  • 103 Front St, Key West, FL 33040
    103 Front St, Key West, FL 33040
    103 Front St, Key West, FL 33040
    /44

    $6,850,000

    • 3 Beds
    • 3 Baths
    • 3,000 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. This home is perfect for entertaining on a large scale or enjoying a quiet evening. A dramatic

    Laura McChesney Preferred Properties (KW)

    103 Front St, Key West, FL 33040
  • 204 Southard St Unit 5, Key West, FL 33040
    204 Southard St Unit 5, Key West, FL 33040
    204 Southard St Unit 5, Key West, FL 33040
    /27

    $865,000

    • 2 Beds
    • 1 Bath
    • 646 Sq Ft

    204 Southard St Unit 5, Key West, FL 33040

    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,

    Stacy Stahl Realty ONE Group Destination

    204 Southard St Unit 5, Key West, FL 33040
  • 514 Emma St, Key West, FL 33040
    514 Emma St, Key West, FL 33040
    514 Emma St, Key West, FL 33040
    /43

    $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

    Behmke The Compass Realty (KW)

    514 Emma St, Key West, FL 33040
  • 401 Emma St Unit H, Key West, FL 33040
    401 Emma St Unit H, Key West, FL 33040
    401 Emma St Unit H, 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
  • 564 Porter Ln, Key West, FL 33040
    564 Porter Ln, Key West, FL 33040
    564 Porter Ln, Key West, FL 33040
    /24

    $1,350,000

    • 2 Beds
    • 2.5 Baths
    • 960 Sq Ft

    564 Porter Ln, Key West, FL 33040

    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

    Behmke The Compass Realty (KW)

    564 Porter Ln, Key West, FL 33040
Florida Monroe County Key West

Real Estate & Homes for Sale in Truman Annex, Key West

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.
Learn more about living in Truman Annex

Truman Annex, Key West, FL Home Prices vs. Nearby Neighborhoods

Truman Annex Mid Town Old Town The Meadows
Median Home Price
$1,395,000
$1,349,500
$1,612,000
$1,479,750
Median Sale Price
$1,220,000
+18% YoY
$1,121,250
+15% YoY
$1,400,000
+6% YoY
$1,469,500
-20% YoY
Median Single Family Price
$1,347,500
$1,330,000
$1,650,000
$1,525,000
Median Condo Price
$932,500
$889,000
$951,000
$669,000
Total Active Listings
5 listings
65 listings
82 listings
5 listings
Market Conditions
2 Months of Supply
Seller's Market
7 Months of Supply
Buyer's Market
7 Months of Supply
Buyer's Market
7 Months of Supply
Buyer's Market

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 fairly dense in population with 11.0 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.
How much do you need to make to afford a house in Truman Annex?
The median home price in Truman Annex is $1,395,000. If you put a 20% down payment of $279,000 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $7,170 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $307K 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, The Meadows, Casa Marina, Mid Town and New Town.
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