$2,104,493Average Value$1,497Average Price per Sq Ft21Homes For Sale
It all began with a Little White House
When President Harry S. Truman spent winters at his little white house in Key West, he had no idea what legacy he would leave behind. Decades later, his house remains, surrounded by a delicately landscaped and gated community known as Truman Annex. Tropical foliage and fruit trees peek around white picket fences, and shaded sidewalks make the area comfortably walkable. As the city's only planned, private neighborhood, it’s become one of the most coveted and expensive — something local Realtors say isn’t a deterrent for serious buyers. “They understand that this is a special place. It’s one of the reasons they’re buying here,” says Truman Annex resident Mike Caron, a Realtor with Keller Williams Compass Realty. The community’s location along the waterfront is within a few blocks of Mallory Square, known for its historic sunset celebrations, and Duval Street, a hub for shopping, dining and nightlife.
Previously part of Fort Zachary Taylor, a U.S. military base established in 1845, the area was annexed to the Key West Naval Station and became a haven for Truman, who spent 175 days living and working in the community until 1952. Now, the gates of this nationally registered historic district remain open from 8 a.m. to 6 p.m., allowing pedestrians and bicyclists to visit Truman’s house, which is now the Harry S. Truman Little White House Museum.
Truman Annex all began with the The Truman Little White which today is a museum.
The entrance to Truman Annex is on the intersection of Southard St and Thomas St.
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From historic naval buildings to housing units
Housing options in Truman Annex offer a little bit of everything, from classic Southern Cottage-style row homes to three-story townhouses to grand Italian Revival homes. What unites each separate section, however, is the color. In keeping with the historic theme of the Little White House, most outward-facing structures are painted white, creating a uniform look despite a range of styles and sizes. Some multi-unit properties took over decommissioned military buildings, such as The Foundry’s townhouses and Harbour Place condos, the latter of which took over the former naval officers' headquarters. Developments like Shipyard Condos come with amenities such as a large community pool, while townhouses in President’s Walk feature private courtyards. Two-bedroom condos can sell for $700,000 to $1 million, and most townhouses are priced between $1.2 million and $2 million. Single-family homes, which range from cozy two-bedrooms to massive five-bedroom estates, generally cost between $2 million and $7 million.
Many Truman Annex properties allow weekly and monthly rentals, which Caron says makes them popular with owners who only spend part of the year on the island. “It’s always been a big, big advantage, as far as the Annex is concerned. There are a number of residents who rent their houses out for the season. They’ll start in November or December and go right to April, and then they might live in it themselves the rest of the time.”
Truman Annex is a bike friendly community with residential streets having sidewalks.
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Sunsets at Truman Waterfront Park are a local tradition
Truman Waterfront Park, a 33-acre expanse that reopened in 2018 after renovations, is a local destination for its massive playground, splash pad and manicured lawn. But Caron says it's especially popular in the evening. “If you don’t want the hubbub of performers at Mallory Square, and you just want to see the sunset, then you go straight down to the end of Southern Street and run right into Truman Waterfront Park.” A paved path wraps around the waterfront, creating space for casual fishing, dog walking and biking. “That’s a very local spot,” says 40-year Key West resident Brenda Donnelly, broker and owner of Brenda Donnelly Real Estate. “People can go on the Coast Guard Ingham Maritime Museum boat for five bucks, have a couple of beers, a glass of wine, and watch the sunset.” Chimes from the nearby Naval Air Station ring out as the sun dips below the horizon, painting the sky with streaks of crimson and coral.
Key West Amphitheater hosts big-name musical acts and borders the entrance to Fort Zachary Taylor Historic State Park. Covering 54 acres, the state park includes historic naval structures, shaded trails, picnic areas and one of the most popular beaches on the island for swimming, snorkeling and scuba diving. This state park has a small admission fee, so many residents get an annual pass for easy entry.
Many residents of Truman Annex can enjoy watching the sunset from Mallory Square.
Many residents of Truman Annex can enjoy fishing at the Truman Waterfront Park.
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Dining and dancing on Duval
Stepping out of Truman Annex and onto Duval Street is like entering another world that hums with excitement and energy. Here, popular bars and restaurants such as Hog’s Breath Saloon and Sloppy Joe’s — a favorite of former resident and author Ernest Hemingway — are almost always busy, whether it’s the height of winter tourism or the middle of hurricane season. The walkable street is lined with shops, galleries and local businesses, including longstanding institutions such as the Green Parrot, which Caron says he visits weekly for live music. “The amount of talent that comes down here on a regular basis is pretty interesting,” he says. “It’s one of the biggest music scenes you’ll ever see. It’s heavily from New Orleans, from Nashville and from South Carolina.” He adds that indoor music venues are even more alluring when bad weather hits. “A Sunday afternoon on a rainy day, you might find yourself listening to jazz at the Green Parrot because that’s the tradition.” And when the sun goes down, Duval Street’s bar scene lights up.
But the options don’t end outside Duval Street, as other popular establishments include Blue Heaven, known for its mile-high Key lime pie, and First Flight, which touts itself as the southernmost microbrewery in the country. Since 1984, family-owned El Meson de Pepe has gained a reputation for serving some of the city’s most authentic Cuban food in a pre-Civil War warehouse. Cuban Coffee Queen has become a favorite stop for those exploring the local art sold at Clinton Square Market. Gourmet groceries are available at Fausto’s Food Palace, locally owned since the 1920s, while retail options and national grocers such as Publix and Winn-Dixie are about 3 miles away in New Town.
Bars, pizzerias and more can be found on Duval Street.
Many of the restaurants on Duval Street offer open air seating just minutes from Truman Annex.
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The Custom House brings history to life
In stark contrast to the bustle of Duval Street are the city’s museums and cultural attractions, many of which are within walking distance of Truman Annex. The Custom House, a towering red brick mansion from the 1890s, now houses the city’s Museum of Art & History. Locals catch shows at the Waterfront Playhouse, one of Florida's oldest continually running theaters, or stop in for stand-up at Comedy Key West, which a local charter boat captain owns. Kids adore the Key West Aquarium, while nautical history buffs often head to Mel Fisher’s Treasure Museum. Contemporary culture also has a home here: The Studios of Key West features a mix of galleries and lofts used by the city’s current artists-in-residence. Author Judy Blume owns the attached bookstore and often spends winter in Key West.
Tropic Cinema opened its doors in 2004 and has weekly showtimes.
Sloppy Joes is a Key West staple on Duval St and is home to the Sloppy Joe sandwich.
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Citywide traditions include Hemingway Days, boat parades
In addition to nightly sunset celebrations at Mallory Square and weekly farmers markets at Truman Waterfront Park, residents can expect a lively calendar of citywide events throughout the year. Annual traditions include Hemingway Days, a week-long festival in July that celebrates the famed author and former resident with lookalike contests, parades, street fairs, fishing tournaments and more. Other summer standouts include the Rotary Club’s Patriotic Party, a Fourth of July event that culminates with a firework display over Indigenous Park. Musicians gather for the annual Key West Songwriters Festival in spring, while fall brings Fantasy Fest and a highly regarded film festival. And in winter, locals and tourists look forward to the city’s holiday boat parade.
Key West High School offers dual enrollment
Gerald Adams Elementary receives a B from Niche and serves kindergarten through fifth grade. B-plus-rated Sigsbee Charter School, located on Dredgers Key, is an option for students of the neighborhood’s military families. Horace O’Bryant School, a B-rated kindergarten through eighth grade option, is the designated middle school for Gerald Adams students, who can then attend B-plus-rated Key West High School. In addition to its own STEM-focused public charter high school, The College of the Florida Keys partners with Key West High to offer dual enrollment courses. As part of Florida’s Monroe County School District, students can apply to any district school. Bus transportation, however, is only offered for students attending their zoned schools. Private options include the Montessori Children’s School of Key West, May Sands Montessori, and The Basilica School of Saint Mary Star of the Sea. This longstanding Catholic institution recently reopened its high school program.
Gerald Adams Elementary offers students in the area educational studies.
Key West High School are home to the conchs and offer learning to students in the area.
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Truman Annex is highly walkable
Shaded sidewalks and fewer cars make Truman Annex an extremely walkable neighborhood. Many locals also navigate the streets by bike. The Lower Keys Shuttle provides bus service throughout the city, offering routes 50 miles north to Marathon. Key West International Airport is 4 miles away.
Truman Annex is located at the end of Key West near Mallory Square.
A public bus system runs throughout Truman Annex and Key West.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Interested in learning more about homes in this area?
Reach out to
Darrin Smith,
an experienced agent in this neighborhood.
Parks in this Area
Truman Waterfront Park
Truman Annex Park
Transit
Airport
Key West International
11 min drive
Bus
Whitehead & Southard
Bus
Truman Waterfront Park- Water Park Area
Bus
Whitehead & Eaton
Bus
Whitehead & Greene St.
Crime and Safety
1 - Low Crime, 10 - High Crime
Truman Annex
US
Homicide
3
4
Sexual Assault
4
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
8
4
Motor Vehicle Theft
5
4
Larceny
7
4
Crime Score
5
4
Source: WhatIsMyCrimeRisk.com
Demographics and Home Trends
On average, homes in Truman Annex, Key West sell after 64 days on the market compared to the national average of 47 days. The average sale price for homes in Truman Annex, Key West over the last 12 months is $1,856,928, up 2% from the average home sale price over the previous 12 months.
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 &
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
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 GroupKeller Williams Key West Compass Realty
Interested in learning more about homes in this area?
Reach out to
Darrin Smith,
an experienced agent in this neighborhood.
Average Home Value
Source: Public Records
Property Mix - Square Feet
This Neighborhood Has More Owners
Demographics
Total Population
665
Median Age
58
Population Density
11 ppl/acre
Population under 18
10.7%
Below the national average
23.8%
Population over 65
35.2%
Above the national average
19.1%
Finances
Median Household Income
$121,505
Significantly above the national average
$71,702
Average Household Income
$149,868
Education and Workforce
High School Graduates
100%
College Graduates
73.2%
Significantly above the national average
34.1%
Advanced Degrees
33.3%
Above the national average
13.3%
% Population in Labor Force
70.7%
Area Factors
Very Bikeable
Bike Score®
82/ 100
Walker's Paradise
Walk Score®
91/ 100
Some Transit
Transit Score®
28/ 100
Source: Walk Score
Source: Walk Score
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
