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!
(60)
Listing Courtesy of Island Home Realty Inc.
(6)
Listing Courtesy of Island Home Realty Inc.
Virtual Tour
(89)
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)
(46)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Virtual Tour
(46)
Listing Courtesy of Truman & Co. (KW)
Open House:
Jan 17, 2026, 11:00 AM - 1:00 PM
(54)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Virtual Tour
(71)
Listing Courtesy of Suzanne Moore Real Estate
(85)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Open House:
Jan 17, 2026, 11:00 AM - 1:00 PM
Virtual Tour
(48)
Listing Courtesy of Truman & Co. (KW)
Listing No. 615623
Listing Courtesy of Island Home Realty Inc.
Listing No. 615688
Listing Courtesy of Island Home Realty Inc.
Listing No. 613995
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. 617783
Listing Courtesy of Brenda Donnelly Real Estate LLC
Listing No. 617020
Listing Courtesy of Truman & Co. (KW)
Open House:
Jan 17, 2026, 11:00 AM - 1:00 PM
Listing No. 616913
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Listing No. 617209
Listing Courtesy of Suzanne Moore Real Estate
Listing No. 617513
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Open House:
Jan 17, 2026, 11:00 AM - 1:00 PM
Listing No. 617845
Listing Courtesy of Truman & Co. (KW)
(60)
$7,995,000
11 11 Beds
11 11 Baths
3,034 Sqft 3,034 Sqft
615623 Listing No. 615623
House Property Type: House
(60)
Listing Courtesy of Island Home Realty Inc.
(6)
$1,900,000
3 3 Beds
1 1 Baths
1,368 Sqft 1,368 Sqft
615688 Listing No. 615688
House Property Type: House
(6)
Listing Courtesy of Island Home Realty Inc.
VIRTUAL TOUR
(89)
$7,495,000
5 5 Beds
5 | 2 5 | 2 Baths
4,000 Sqft 4,000 Sqft
613995 Listing No. 613995
House Property Type: House
VIRTUAL TOUR
(89)
Listing Courtesy of Truman & Co. (KW)
(78)
$6,895,000
6 6 Beds
6 | 1 6 | 1 Baths
3,340 Sqft 3,340 Sqft
617122 Listing No. 617122
House Property Type: House
(78)
Listing Courtesy of RE/MAX Keys Connection (KW)
(71)
$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)
(46)
$5,895,000
6 6 Beds
6 | 1 6 | 1 Baths
3,443 Sqft 3,443 Sqft
617783 Listing No. 617783
House Property Type: House
(46)
Listing Courtesy of Brenda Donnelly Real Estate LLC
VIRTUAL TOUR
(46)
$5,395,000
4 4 Beds
4 | 1 4 | 1 Baths
3,336 Sqft 3,336 Sqft
617020 Listing No. 617020
House Property Type: House
VIRTUAL TOUR
(46)
Listing Courtesy of Truman & Co. (KW)
Open House: Jan 17, 2026, 11:00 AM - 1:00 PM
(54)
$5,000,000
5 5 Beds
5 | 1 5 | 1 Baths
2,230 Sqft 2,230 Sqft
616913 Listing No. 616913
House Property Type: House
(54)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
VIRTUAL TOUR
(71)
$4,995,000
4 4 Beds
3 | 1 3 | 1 Baths
3,026 Sqft 3,026 Sqft
617209 Listing No. 617209
House Property Type: House
VIRTUAL TOUR
(71)
Listing Courtesy of Suzanne Moore Real Estate
(85)
$4,950,000
4 4 Beds
5 | 1 5 | 1 Baths
3,092 Sqft 3,092 Sqft
617513 Listing No. 617513
House Property Type: House
(85)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Open House: Jan 17, 2026, 11:00 AM - 1:00 PM
VIRTUAL TOUR
(48)
$4,699,000
4 4 Beds
4 | 1 4 | 1 Baths
3,624 Sqft 3,624 Sqft
617845 Listing No. 617845
House Property Type: House
VIRTUAL TOUR
(48)
Listing Courtesy of Truman & Co. (KW)
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.