Truman Annex

Welcome to Truman Annex

A gated oasis within Old Town, Truman Annex combines rich history with elegant tranquility. Named after President Harry S. Truman, who used the former naval station’s commanding officer’s quarters as his “Little White House” during winter retreats, the area has been beautifully transformed into a prestigious residential community.

Today, the Harry S. Truman Little White House Museum anchors the neighborhood, surrounded by meticulously restored military quarters, lush landscaping, and quiet, palm-shaded streets. The architecture blends Colonial Revival and Key West tropical styles, creating a picture- perfect retreat.

Residents of Truman Annex enjoy proximity to both Fort Zachary Taylor State Park—home to one of the island’s best beaches—and the lively energy of downtown, just outside the gate. It’s where serenity and sophistication meet Key West’s storied past.

Our Top Listings

Featured Properties

Handpicked homes and properties that represent the best of Key West living — luxury, location, and lifestyle.

For Sale
$11,500,000

412 Frances Street, Key West, FL 33040
- 15 Beds
- 18 Baths
- 5,731 Sq.Ft.
For Sale
$7,495,000

616 Eaton Street, Key West, FL 33040
- 5 Beds
- 7 Baths
- 4,000 Sq.Ft.
For Sale
$5,595,000

1006-1008 Fleming Street, Key West, FL 33040
- 4 Beds
- 5 Baths
- 3,336 Sq.Ft.
For Sale
$4,650,000

1523 Patricia Street, Key West, FL 33040
- 4 Beds
- 3 Baths
- 3,154 Sq.Ft.
For Sale
$4,595,000

1113 Stump Lane, Key West, FL 33040
- 4 Beds
- 5 Baths
- 2,985 Sq.Ft.
Active Under Contract
$3,599,000

1020 Southard Street, Key West, FL 33040
- 3 Beds
- 4 Baths
- 2,438 Sq.Ft.
For Sale
$3,595,000

33 Cypress Avenue, Key Haven, FL 33040
- 4 Beds
- 5 Baths
- 4,102 Sq.Ft.
For Sale
$2,400,000

1109 Stump Lane, Key West, FL 33040
- 3 Beds
- 4 Baths
- 1,724 Sq.Ft.
For Sale
$2,299,999

17210 Angelfish Lane, Sugarloaf Key, FL 33042
- 3 Beds
- 3 Baths
- 2,288 Sq.Ft.
For Sale
$2,299,999

17210 Angelfish Lane, Sugarloaf Key, FL 33042
- 3 Beds
- 3 Baths
- 2,288 Sq.Ft.
For Sale
$2,249,000

1706 Seminary Street, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,938 Sq.Ft.
For Sale
$1,995,000

1229 5Th Street, Key West, FL 33040
- 6 Beds
- 3 Baths
- 3,197 Sq.Ft.
For Sale
$1,949,000

3841 N Roosevelt Boulevard Unit: 315, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,357 Sq.Ft.
For Sale
$1,949,000

3841 N Roosevelt Boulevard Unit: 332, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,357 Sq.Ft.
For Sale
$1,800,000

408 William Street, Key West, FL 33040
- 4 Beds
- 3 Baths
- 1,943 Sq.Ft.
For Sale
$1,799,000

17213 Starfish Lane, Sugarloaf Key, FL 33042
- 3 Beds
- 2 Baths
- 1,750 Sq.Ft.
For Sale
$1,799,000

17213 Starfish Lane, Sugarloaf Key, FL 33042
- 3 Beds
- 2 Baths
- 1,750 Sq.Ft.
For Sale
$1,399,900

1317 Newton Street, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,386 Sq.Ft.
For Sale
$1,325,000

247 Golf Club Drive, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,600 Sq.Ft.
For Sale
$999,000

3841 N Roosevelt Boulevard Unit: 222, Key West, FL 33040
- 3 Beds
- 3 Baths
- 1,586 Sq.Ft.
For Sale
$995,000

701 Spanish Main Drive Unit: 221, Cudjoe Key, FL 33042
- 2 Beds
- 2 Baths
- 864 Sq.Ft.
For Sale
$899,000

3841 N Roosevelt Boulevard Unit: 213, Key West, FL 33040
- 2 Beds
- 3 Baths
- 1,357 Sq.Ft.
For Sale
$859,500

3705 Eagle Avenue, Key West, FL 33040
- 6,000 Sq.Ft.
For Sale
$859,500

3711 Eagle Avenue, Key West, FL 33040
- 2 Beds
- 2 Baths
- 1,464 Sq.Ft.
For Sale
$825,000

1206 White Street, Key West, FL 33040
- 1 Bath
For Sale
$799,999

1200 White Street, Key West, FL 33040
- 1 Bath
For Sale
$735,000

1202 White Street, Key West, FL 33040
- 1 Bath
For Sale
$725,000

17220 Angelfish Lane, Sugarloaf Key, FL 33042
- 8,165 Sq.Ft.
For Sale

$725,000

17220 Angelfish Lane, Sugarloaf Key, FL 33042
For Sale

$725,000

17230 Angelfish Lane, Sugarloaf Key, FL 33042
For Sale
$725,000

17230 Angelfish Lane, Sugarloaf Key, FL 33042
- 8,165 Sq.Ft.
For Sale
$665,000

1124 Catherine Street Unit: 202, Key West, FL 33040
- 2 Beds
- 1 Bath
- 677 Sq.Ft.
For Sale
$600,000

701 Spanish Main Drive Unit: 384, Cudjoe Key, FL 33042
- 2,308 Sq.Ft.
For Sale
$584,000

3930 S 3930 Roosevelt Boulevard Unit: N302, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,075 Sq.Ft.
For Sale
$550,000

3930 S Roosevelt Boulevard Unit: E104, Key West, FL 33040
- 3 Beds
- 2 Baths
- 1,062 Sq.Ft.
For Sale
$465,000

1124 Catherine Street Unit: 201, Key West, FL 33040
- 1 Bed
- 1 Bath
- 454 Sq.Ft.
For Sale
$455,000

31129 Avenue G, Big Pine Key, FL 33043
- 3 Beds
- 3 Baths
- 844 Sq.Ft.
For Sale

$300,000

5555 College Road Unit: 9 (Sailfish), Key West, FL 33040