Old Town
Old Town is the heartbeat of Key West. Comprised of quiet lanes, beautiful architecture, and deep history, there is not much like it! The streets are very walkable and all the conveniences are right out your front door.
Old Town Homes are unique, from Grand Victorian Estates to shotgun style cottages, you could spend hours gazing at all of the details that make these homes special. The people are friendly, and there’s always something to do.
A typical day includes Cuban coffee on the porch, breakfast at Blue Heaven with the roosters, and boutique hopping on Duval Street. Grab groceries at Fausto’s, relax by your pool, and watch sunset performers at Mallory Square. End the day with cocktails at The Roost on Fleming Street.
Life in Old Town is simple and sweet. Old Town is the place for you if you’re looking for a slower pace and friendly faces!
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Listing Courtesy of Island Home Realty Inc.
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Listing Courtesy of Island Home Realty Inc.
(88)
Listing Courtesy of RE/MAX Keys Connection (KW)
(80)
Listing Courtesy of RE/MAX Keys Connection (KW)
Virtual Tour
(41)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Virtual Tour
(51)
Listing Courtesy of Truman & Co. (KW)
(37)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Virtual Tour
(42)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Virtual Tour
(91)
Listing Courtesy of Coldwell Banker Schmitt Real Estate Co. (KW)
(45)
Listing Courtesy of Suzanne Moore Real Estate
Open House:
Oct 24, 2026, 11:00 AM - 1:00 PM
Virtual Tour
(30)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Virtual Tour
(49)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Listing No. 620880
Listing Courtesy of Island Home Realty Inc.
Listing No. 621278
Listing Courtesy of Island Home Realty Inc.
Listing No. 621466
Listing Courtesy of RE/MAX Keys Connection (KW)
Listing No. 621141
Listing Courtesy of RE/MAX Keys Connection (KW)
Listing No. 621215
Listing Courtesy of Brenda Donnelly Real Estate LLC
Listing No. 621632
Listing Courtesy of Truman & Co. (KW)
Listing No. 618470
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Listing No. 620343
Listing Courtesy of Brenda Donnelly Real Estate LLC
Listing No. 618468
Listing Courtesy of Coldwell Banker Schmitt Real Estate Co. (KW)
Listing No. 621485
Listing Courtesy of Suzanne Moore Real Estate
Open House:
Oct 24, 2026, 11:00 AM - 1:00 PM
Listing No. 620985
Listing Courtesy of Brenda Donnelly Real Estate LLC
Listing No. 620913
Listing Courtesy of Brenda Donnelly Real Estate LLC
(6)
$1,800,000
3 3 Beds
1 1 Baths
1,368 Sqft 1,368 Sqft
620880 Listing No. 620880
House Property Type: House
(6)
Listing Courtesy of Island Home Realty Inc.
(36)
$950,000
2 2 Beds
1 1 Baths
610 Sqft 610 Sqft
621278 Listing No. 621278
House Property Type: House
(36)
Listing Courtesy of Island Home Realty Inc.
(88)
$6,895,000
6 6 Beds
6 | 1 6 | 1 Baths
3,425 Sqft 3,425 Sqft
621466 Listing No. 621466
House Property Type: House
(88)
Listing Courtesy of RE/MAX Keys Connection (KW)
(80)
$6,750,000
5 5 Beds
4 | 1 4 | 1 Baths
3,663 Sqft 3,663 Sqft
621141 Listing No. 621141
House Property Type: House
(80)
Listing Courtesy of RE/MAX Keys Connection (KW)
VIRTUAL TOUR
(41)
$5,400,000
6 6 Beds
6 | 1 6 | 1 Baths
2,993 Sqft 2,993 Sqft
621215 Listing No. 621215
House Property Type: House
VIRTUAL TOUR
(41)
Listing Courtesy of Brenda Donnelly Real Estate LLC
VIRTUAL TOUR
(51)
$4,950,000
4 4 Beds
4 4 Baths
2,441 Sqft 2,441 Sqft
621632 Listing No. 621632
House Property Type: House
VIRTUAL TOUR
(51)
Listing Courtesy of Truman & Co. (KW)
(37)
$4,695,000
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
VIRTUAL TOUR
(42)
$3,800,000
3 3 Beds
3 3 Baths
1,933 Sqft 1,933 Sqft
620343 Listing No. 620343
House Property Type: House
VIRTUAL TOUR
(42)
Listing Courtesy of Brenda Donnelly Real Estate LLC
VIRTUAL TOUR
(91)
$3,750,000
7 7 Beds
7 | 1 7 | 1 Baths
3,015 Sqft 3,015 Sqft
618468 Listing No. 618468
House Property Type: House
VIRTUAL TOUR
(91)
Listing Courtesy of Coldwell Banker Schmitt Real Estate Co. (KW)
(45)
$3,750,000
3 3 Beds
3 | 1 3 | 1 Baths
2,421 Sqft 2,421 Sqft
621485 Listing No. 621485
House Property Type: House
(45)
Listing Courtesy of Suzanne Moore Real Estate
Open House: Oct 24, 2026, 11:00 AM - 1:00 PM
VIRTUAL TOUR
(30)
$3,700,000
3 3 Beds
3 | 1 3 | 1 Baths
1,366 Sqft 1,366 Sqft
620985 Listing No. 620985
House Property Type: House
VIRTUAL TOUR
(30)
Listing Courtesy of Brenda Donnelly Real Estate LLC
VIRTUAL TOUR
(49)
$3,600,000
4 4 Beds
4 4 Baths
2,691 Sqft 2,691 Sqft
620913 Listing No. 620913
Condo Property Type: Condo
VIRTUAL TOUR
(49)
Listing Courtesy of Brenda Donnelly Real Estate LLC
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