Key West Real Estate | Key West Homes and Condos for Sale
  • Home
  • Advanced Search
  • Market Report
  • Buyers
  • Sellers
  • Meet Chris
  • Blog
Login
305-707-4821

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Search for Homes in the Truman Annex

TO
Advanced Search

Address Search

The Truman Annex Homes for Sale

The Truman Annex used to be a Navy Base. It's named after our former President Harry S. Truman because that was his winter retreat home and it's located in Old Town Key West. You should check out the Little Whitehouse if you haven't already. If you are familiar with Key West than you know this is a convenient location in Old Town because you are walking distance to Duval Street, Fort Zachary Beach and other fine amenities this island has to offer. This is a private gated community and has different homes/styles to choose from.

In the historic Old Town of Key West, Florida, you’ll find the prestigious district of Truman Annex, named after President Harry Truman it is the home of the “Little White House.” The Little White House is a grand historic home built in 1890, was used as the winter retreat of the President in the late 1940’s, and today it is known as the Harry S. Truman Little White House Museum. Truman Annex is a 6-block planned luxury community of tropical beauty designed to encapsulate the unique spirit of historic Key West. The neighborhood is found on the western edge of Old Town and is bounded by Southard, Front and Whitehead Streets.

Truman Annex real estate consists of multi-million dollar Key West homes, condos, and townhouses within several distinct neighborhoods. You can find historic Italian and Greek Revival homes renovated as gorgeous luxury mansions with white picket fences and perfectly landscaped lawns. At the southern end of Truman Annex, you’ll find a collection of Southern Cottage style homes with tin roofs and porches. Adjacent to Mallory Square there is a delightful planned subdivision with a conch cottage design, free-standing homes, and condos with access to picturesque gardens and community swimming pools.

No matter which Truman Annex neighborhood you choose, you'll be in a prime location within walking distance to Mallory Square, Duval Street and other Key West attractions, including the beach at Fort Zachary Taylor State Park. Other neighborhood points of interest include the Mel Fisher Treasure Museum, US Coast Guard Cutter Ingham Maritime Museum, and the Audubon House and Tropical Gardens. The meticulous tropical landscaping gives the community a picturesque park-like ambiance and along upper Duval Street, you’ll find some of Key West’s best entertainment, shopping, and dining. Truman Annex is a sought-after address for high-end vacation rentals and permanent residents desiring to live near the heart of Key West. It is also a popular destination for homebuyers attracted to the exciting culture of Key West and its rich history and heritage. If you would like to learn more about the homes for sale in Truman Annex of Key West, Florida, please don’t hesitate to contact us for more information.

Truman Annex's Newest Listings

208 Southard Unit 6, Key West image
208 Southard Unit 6, Key West $892,000

Rarest of the rare, this downstairs Shipyard condo is now for sale. This is one of only six units that flow from side to side (rather than front to back) and is set back ...

  • 2 Beds
  • 2 Baths
  • 605479 MLS
107 Front Unit 217, Key West image
107 Front Unit 217, Key West $3,750,000

Rarely do units become available in the Harbour Place condominiums in Truman Annex, making this property an investor's dream come true, complete with a transient rental l...

  • 4 Beds
  • 4 Baths
  • 605442 MLS
105 Front Unit 119, Key West image
105 Front Unit 119, Key West $1,895,000

This 2 bedroom, 2 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 plent...

  • 2 Beds
  • 3 Baths
  • 605358 MLS
530 Porter, Key West image
530 Porter, Key West $1,365,000 ▼

Opportunity knocks. Beautifully renovated Truman Annex townhouse- 'Salty Kisses' -conveys with special limited transient rental license in place. Tropical Vibe, light...

  • 2 Beds
  • 2 Baths
  • 605120 MLS
403 Emma Unit B, Key West image
403 Emma Unit B, Key West $1,695,000 ▼

Rare opportunity to own a piece of history in The Truman Annex. This 2 story, 2 bedroom/ 2.5 bathroom villa is located in Mills Place, a quiet and peaceful 20 unit condom...

  • 2 Beds
  • 3 Baths
  • 604868 MLS
620 Thomas Unit 297, Key West image
620 Thomas Unit 297, Key West $895,000 ▼

2 bedroom, 2 bath upstairs spacious unit in Truman Annex with one assigned parking space. Bright and Airy floor plan with cathedral ceilings, and balcony. Recently renova...

  • 2 Beds
  • 2 Baths
  • 604825 MLS
64 Front, Key West image
64 Front, Key West $4,800,000

Spectacular home in great location in the award-winning Truman Annex.This beautiful home custom built in 1989, includes five bedrooms and five bathrooms.There are four se...

  • 5 Beds
  • 5 Baths
  • 604823 MLS
620 Thomas Unit 284, Key West image
620 Thomas Unit 284, Key West $849,000

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...

  • 2 Beds
  • 1 Baths
  • 604685 MLS
206 Southard Unit 4, Key West image
206 Southard Unit 4, Key West $875,000

Take a look at Pelican, a nicely furnished and renovated upstairs Shipyard condo. This 2 bedroom/1 bathroom unit is perfectly set up for you to enjoy all that Key West ha...

  • 2 Beds
  • 1 Baths
  • 604658 MLS
518 Emma, Key West image
518 Emma, Key West $3,399,000 ▼

Beautiful Truman Annex. Open floor plan with 3 sets of French Doors that open up to your private tropical Oasis, with a stunning lagoon shaped pool with rock waterfall. ...

  • 4 Beds
  • 3 Baths
  • 604612 MLS
202 Southard Unit 11, Key West image
202 Southard Unit 11, Key West $809,000

This one bedroom condo is a little slice of paradise. It's located in the gated community of The Shipyard in Truman Annex, so you're close to all the action but far enoug...

  • 1 Beds
  • 1 Baths
  • 604206 MLS
302 Southard Unit 3 Units for Sale, Key West image
302 Southard Unit 3 Units for Sale, Key West $383,725

Now available is a majority interest in the Courthouse Business Center. Offered are 3 of the 37 individual units. These popular one-room offices were built new in 2001. L...

  • 4 Baths
  • 603997 MLS
101 Front Unit 23, Key West image
101 Front Unit 23, Key West $1,540,000 ▼

Showings now easily accommodated, after a long winter & spring of vacation rental bookings! Imagine waking up in a living Key West travel brochure. Sun dancing through s...

  • 2 Beds
  • 3 Baths
  • 603658 MLS
101 Admirals, Key West image
101 Admirals, Key West $7,900,000

Incredibly private & spectacular property on one of the largest lots in the gated community of Truman Annex, an absolutely stunning old town estate! A wall of tropical fo...

  • 5 Beds
  • 4 Baths
  • 603583 MLS
206 Southard Unit 3, Key West image
206 Southard Unit 3, Key West $898,000

This is a ground floor condo that the seller will be converting back to the original 2-bedroom layout. It currently offers an expanded living area with two sets of impact...

  • 2 Beds
  • 1 Baths
  • 603549 MLS

Address Search

Like or Share
Loading likes...
Christopher Orth

Christopher Orth

National REALTOR Magazine's
30-Under-30 Award Recipient

  |  

Resources
  • Featured Listings
  • History Of Key West
  • Mission Statement
  • Neighborhoods
  • Neighborhood Info
  • Points of Interest
  • Testimonials
  • Vendor List
Key West Neighborhoods
  • Casa Marina
  • Key West Golf Club
  • Mid Town East
  • Mid Town West
  • New Town
  • Old Town-N of Truman
  • Old Town-S of Truman
  • Outside of Key West
  • Sunset Key
  • The Meadows
  • Truman Annex
Quick Price Range Search
  • $150'k to $250'k
  • $250'k to $300'k
  • $300'k to $400'k
  • $400'k to $500'k
  • $500'k to $600'k
  • $600'k to $700'k
  • $700'k to $800'k
  • $800'k to $900'k
  • $900'k to $1M
  • $1M to $1.25M
  • $1.25M to $1.5M
  • $1.5M to $1.75M
  • $1.75M to $2M
  • $2M and Over

Key West Real Estate Map Search

Interactive Map Search

 

Buying & Selling Made Easy

  Freshest Data Available
  Active Listings Only
  Customizable Search Options
  New Listing Alerts
  Instant Home Value Assessments

 

Connect With Me

 
  • Home
  • Advanced Search
  • Featured Properties
  • Buyers
  • Sellers
  • Market Report
  • Meet Chris
  • Blog


Christopher Orth
National REALTOR Magazine's
30-Under-30 Award Recipient 

336 Duval Street
Key West, FL 33040

Phone 1: 305-707-4821
Phone 2: 267-980-2260
Email: ChrisOrthKeyWest@gmail.com



© All Rights Reserved | Privacy Policy

©2023 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity. 

Advanced Search

  • Casa Marina
  • Old Town-N of Truman
  • Old Town-S of Truman
  • Sunset Key
  • Mid Town West
  • Mid Town East
  • The Meadows
  • Truman Annex
  • New Town
  • Key West Golf Club
IDX Real Estate Websites by
• Accessibility • Terms • Privacy