Old Town Key West
Old Town Key West encompasses the historic neighborhoods north and south of Truman Avenue and is widely regarded as the cultural heart of the island. Rich in history, architecture, and local character, this area attracts buyers seeking walkability to restaurants, galleries, attractions, and the Historic Seaport. Many buyers exploring Old Town Key West homes for sale are drawn to the neighborhood’s distinctive architectural styles and vibrant street life. North of Truman Avenue, an area originally settled by Bahamians in the 1800s, features classic shotgun houses, traditional Conch homes, and elegant Victorian residences. South of Truman Avenue, Cuban cigar makers once settled to escape conflict, leaving behind beautifully preserved Conch Revival homes and historic cigar maker cottages. Old Town is also home to well-known landmarks such as Sunset Pier, Duval Street, and The Waterfront Playhouse. For those seeking a strong sense of place, timeless architecture, and a true island lifestyle, Old Town Key West homes for sale offer a rare opportunity to live in one of the most iconic neighborhoods in the Florida Keys.
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Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 2, 2026, 12:00 PM - 3:00 PM
(40)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 3, 2026, 12:00 PM - 2:00 PM
Virtual Tour
(36)
Listing Courtesy of Brenda Donnelly Real Estate LLC
(27)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 3, 2026, 12:00 PM - 3:00 PM
(17)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Virtual Tour
(62)
Listing Courtesy of Truman & Co. (KW)
(78)
Listing Courtesy of RE/MAX Keys Connection (KW)
(71)
Listing Courtesy of RE/MAX Keys Connection (KW)
Virtual Tour
(38)
Listing Courtesy of Truman & Co. (KW)
(88)
Listing Courtesy of Preferred Properties (KW)
Virtual Tour
(60)
Listing Courtesy of Truman & Co. (KW)
(37)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Listing No. 617116
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 2, 2026, 12:00 PM - 3:00 PM
Listing No. 619579
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 3, 2026, 12:00 PM - 2:00 PM
Listing No. 618279
Listing Courtesy of Brenda Donnelly Real Estate LLC
Listing No. 619523
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 3, 2026, 12:00 PM - 3:00 PM
Listing No. 619321
Listing Courtesy of Brenda Donnelly Real Estate LLC
Listing No. 619282
Listing Courtesy of Truman & Co. (KW)
Listing No. 617122
Listing Courtesy of RE/MAX Keys Connection (KW)
Listing No. 617175
Listing Courtesy of RE/MAX Keys Connection (KW)
Listing No. 617923
Listing Courtesy of Truman & Co. (KW)
Listing No. 617710
Listing Courtesy of Preferred Properties (KW)
Listing No. 618363
Listing Courtesy of Truman & Co. (KW)
Listing No. 618470
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
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$3,899,000
4 4 Beds
3 3 Baths
2,271 Sqft 2,271 Sqft
617116 Listing No. 617116
House Property Type: House
(55)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House: May 2, 2026, 12:00 PM - 3:00 PM
(40)
$2,675,000
3 3 Beds
3 | 1 3 | 1 Baths
1,962 Sqft 1,962 Sqft
619579 Listing No. 619579
House Property Type: House
(40)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House: May 3, 2026, 12:00 PM - 2:00 PM
VIRTUAL TOUR
(36)
$2,495,000
4 4 Beds
3 3 Baths
2,058 Sqft 2,058 Sqft
618279 Listing No. 618279
House Property Type: House
VIRTUAL TOUR
(36)
Listing Courtesy of Brenda Donnelly Real Estate LLC
(27)
$1,325,000
2 2 Beds
2 | 1 2 | 1 Baths
1,277 Sqft 1,277 Sqft
619523 Listing No. 619523
House Property Type: House
(27)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House: May 3, 2026, 12:00 PM - 3:00 PM
(17)
$775,000
2 2 Beds
2 2 Baths
862 Sqft 862 Sqft
619321 Listing No. 619321
Condo Property Type: Condo
(17)
Listing Courtesy of Brenda Donnelly Real Estate LLC
VIRTUAL TOUR
(62)
$7,495,000
5 5 Beds
5 | 2 5 | 2 Baths
4,000 Sqft 4,000 Sqft
619282 Listing No. 619282
House Property Type: House
VIRTUAL TOUR
(62)
Listing Courtesy of Truman & Co. (KW)
(78)
$6,895,000
6 6 Beds
6 | 1 6 | 1 Baths
3,425 Sqft 3,425 Sqft
617122 Listing No. 617122
House Property Type: House
(78)
Listing Courtesy of RE/MAX Keys Connection (KW)
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$6,750,000
5 5 Beds
4 | 1 4 | 1 Baths
3,663 Sqft 3,663 Sqft
617175 Listing No. 617175
House Property Type: House
(71)
Listing Courtesy of RE/MAX Keys Connection (KW)
VIRTUAL TOUR
(38)
$5,995,000
5 5 Beds
6 | 1 6 | 1 Baths
4,387 Sqft 4,387 Sqft
617923 Listing No. 617923
House Property Type: House
VIRTUAL TOUR
(38)
Listing Courtesy of Truman & Co. (KW)
(88)
$5,950,000
6 6 Beds
6 | 2 6 | 2 Baths
4,094 Sqft 4,094 Sqft
617710 Listing No. 617710
House Property Type: House
(88)
Listing Courtesy of Preferred Properties (KW)
VIRTUAL TOUR
(60)
$4,990,000
4 4 Beds
4 4 Baths
2,441 Sqft 2,441 Sqft
618363 Listing No. 618363
House Property Type: House
VIRTUAL TOUR
(60)
Listing Courtesy of Truman & Co. (KW)
(37)
$4,750,000
4 4 Beds
4 | 1 4 | 1 Baths
2,716 Sqft 2,716 Sqft
618470 Listing No. 618470
House Property Type: House
(37)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
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