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Truman Annex is a beautifully transformed former Naval station and the historic winter home of President Harry S. Truman, now one of Key West’s most distinctive residential enclaves. This gated community is defined by lush landscaping, tree-lined streets, and a peaceful atmosphere that feels removed from the energy of nearby attractions. Buyers interested in Truman Annex Key West homes for sale appreciate the neighborhood’s unique balance of privacy and proximity, offering easy access to Fort Zachary Taylor Historic State Park, the Truman Waterfront Park, and the shops, dining, and entertainment along Duval Street. Nestled between the Atlantic Ocean and Old Town, Truman Annex features a mix of single-family residences, condominiums, and townhomes, all within a meticulously maintained setting. Whether enjoying waterfront strolls, relaxing in nearby parks, or simply taking in the quiet charm of the streets, residents find that Truman Annex Key West homes for sale offer a rare opportunity to enjoy island living in a secure and beautifully preserved community.
514 Emma Street KEY WEST, FL 33040
$3,600,000
4 Beds 3 Baths 1,920 SqftListing No.: 621135 Property Type: House camera (43) Listing Courtesy of Keller Williams Key West Compass Realty
Details
401 Emma Street #APT H KEY WEST, FL 33040
$2,999,500
2 Beds 2 Baths 1,770 SqftListing No.: 618955 Property Type: House camera (54) Listing Courtesy of Century 21 All Keys Inc (KW)
Details
115 Front Street #APT 101 KEY WEST, FL 33040
$2,250,000
3 Beds 3 Baths 1,250 SqftListing No.: 621771 Property Type: Condo camera (27) Listing Courtesy of Preferred Properties (KW)
Details
101 Front Street #23 KEY WEST, FL 33040
$1,675,000
2 Beds 2 | 1 Baths 1,216 SqftListing No.: 621909 Property Type: Condo camera Virtual Tour camera (52) Listing Courtesy of Truman & Co. (KW)
Details
564 Porter Lane KEY WEST, FL 33040
$1,350,000
2 Beds 2 | 1 Baths 960 SqftListing No.: 619140 Property Type: Condo camera (24) Listing Courtesy of Keller Williams Key West Compass Realty
Details
620 Thomas Street #149 KEY WEST, FL 33040
$869,000
2 Beds 1 Baths 680 SqftListing No.: 621337 Property Type: Condo camera (36) Listing Courtesy of Keller Williams Key West Compass Realty
Details
204 Southard Street #5 KEY WEST, FL 33040
$865,000
2 Beds 1 Baths 646 SqftListing No.: 620303 Property Type: Condo camera (28) Listing Courtesy of Realty ONE Group Destination
Details
514 Emma Street, KEY WEST, FL 33040
For Sale
camera (43)
price

$3,600,000

beds

4 4 Beds

baths

3 3 Baths

lot size

1,920 Sqft 1,920 Sqft

listing no.

621135 Listing No. 621135

property type

House Property Type: House

gallery photos

camera (43)

Listing Courtesy of Keller Williams Key West Compass Realty

401 Emma Street #APT H, KEY WEST, FL 33040
For Sale
camera (54)
price

$2,999,500

beds

2 2 Beds

baths

2 2 Baths

lot size

1,770 Sqft 1,770 Sqft

listing no.

618955 Listing No. 618955

property type

House Property Type: House

gallery photos

camera (54)

Listing Courtesy of Century 21 All Keys Inc (KW)

115 Front Street #APT 101, KEY WEST, FL 33040
For Sale
camera (27)
price

$2,250,000

beds

3 3 Beds

baths

3 3 Baths

lot size

1,250 Sqft 1,250 Sqft

listing no.

621771 Listing No. 621771

property type

Condo Property Type: Condo

gallery photos

camera (27)

Listing Courtesy of Preferred Properties (KW)

101 Front Street #23, KEY WEST, FL 33040
For Sale
camera VIRTUAL TOUR camera (52)
price

$1,675,000

beds

2 2 Beds

baths

2 | 1 2 | 1 Baths

lot size

1,216 Sqft 1,216 Sqft

listing no.

621909 Listing No. 621909

property type

Condo Property Type: Condo

virtual tour

camera VIRTUAL TOUR

gallery photos

camera (52)

Listing Courtesy of Truman & Co. (KW)

564 Porter Lane, KEY WEST, FL 33040
For Sale
camera (24)
price

$1,350,000

beds

2 2 Beds

baths

2 | 1 2 | 1 Baths

lot size

960 Sqft 960 Sqft

listing no.

619140 Listing No. 619140

property type

Condo Property Type: Condo

gallery photos

camera (24)

Listing Courtesy of Keller Williams Key West Compass Realty

620 Thomas Street #149, KEY WEST, FL 33040
For Sale
camera (36)
price

$869,000

beds

2 2 Beds

baths

1 1 Baths

lot size

680 Sqft 680 Sqft

listing no.

621337 Listing No. 621337

property type

Condo Property Type: Condo

gallery photos

camera (36)

Listing Courtesy of Keller Williams Key West Compass Realty

204 Southard Street #5, KEY WEST, FL 33040
For Sale
camera (28)
price

$865,000

beds

2 2 Beds

baths

1 1 Baths

lot size

646 Sqft 646 Sqft

listing no.

620303 Listing No. 620303

property type

Condo Property Type: Condo

gallery photos

camera (28)

Listing Courtesy of Realty ONE Group Destination

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The data relating to real estate on this website comes in part from the Internet Data Exchange (IDX) program of the Key West Association of REALTORS®. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All Information Is Deemed Reliable But Is Not Guaranteed Accurate.
Key West data last updated at November 3, 2026, 3:55 PM ET
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