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!
(6)
Listing Courtesy of Island Home Realty Inc.
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
(90)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Open House:
May 10, 2026, 11:00 AM - 1:00 PM
Virtual Tour
(42)
Listing Courtesy of Truman & Co. (KW)
Virtual Tour
(46)
Listing Courtesy of Suzanne Moore Real Estate
(36)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 9, 2026, 12:00 PM - 3:00 PM
Listing No. 615688
Listing Courtesy of Island Home Realty Inc.
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
Listing No. 617513
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Open House:
May 10, 2026, 11:00 AM - 1:00 PM
Listing No. 616715
Listing Courtesy of Truman & Co. (KW)
Listing No. 616917
Listing Courtesy of Suzanne Moore Real Estate
-
119 Simonton Street KEY WEST, FL 33040
-
$3,850,000
-
Beds 4 Baths 4 Sqft 2,691 Property Type Condo
-
(36)
-
Listing No. 619812
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House:
May 9, 2026, 12:00 PM - 3:00 PM
(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
(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)
(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)
(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)
$4,695,000
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
(90)
$4,695,000
4 4 Beds
5 | 1 5 | 1 Baths
3,092 Sqft 3,092 Sqft
617513 Listing No. 617513
House Property Type: House
(90)
Listing Courtesy of Berkshire Hathaway HomeServices Knight & Gardner Realty
Open House: May 10, 2026, 11:00 AM - 1:00 PM
VIRTUAL TOUR
(42)
$4,450,000
4 4 Beds
4 | 1 4 | 1 Baths
2,985 Sqft 2,985 Sqft
616715 Listing No. 616715
House Property Type: House
VIRTUAL TOUR
(42)
Listing Courtesy of Truman & Co. (KW)
VIRTUAL TOUR
(46)
$3,999,000
3 3 Beds
3 | 1 3 | 1 Baths
2,421 Sqft 2,421 Sqft
616917 Listing No. 616917
House Property Type: House
VIRTUAL TOUR
(46)
Listing Courtesy of Suzanne Moore Real Estate
(36)
$3,850,000
4 4 Beds
4 4 Baths
2,691 Sqft 2,691 Sqft
619812 Listing No. 619812
Condo Property Type: Condo
(36)
Listing Courtesy of Brenda Donnelly Real Estate LLC
Open House: May 9, 2026, 12:00 PM - 3:00 PM
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.