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Homes for Sale in Islamorada, Florida

32 active listings in Islamorada, Monroe County, with a median asking price of $2,950,000. Showing 1–24, priced high to low.

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Featured homes $500,000–$2,000,000

Recently listed in Islamorada, in the range most Islamorada sellers list in.

133 Anglers Way
$1,700,000
133 Anglers Way
Islamorada, FL 33036
2 bd2.5 ba1,170 sqft
Listed by Douglas Elliman
111 ANGLERS Way
$1,199,999
111 ANGLERS Way
Islamorada, FL 33036
2 bd2.5 ba1,376 sqft
Listed by Berkshire Hathaway HomeService
161 Palermo Drive
$1,950,000
161 Palermo Drive
Islamorada, FL 33036
3 bd2 ba1,190 sqft
Listed by Engel & Völkers Islamorada
100 IROQUOIS Drive 5
$999,999
100 IROQUOIS Drive 5
Islamorada, FL 33036
3 bd3 ba1,710 sqft
Listed by Coldwell Banker Schmitt Real E
81801 Old Highway 754
$649,000
81801 Old Highway 754
Islamorada, FL 33036
1 bd1 ba550 sqft
Listed by American Caribbean Real Estate
118 Cortez Drive B
$649,000
118 Cortez Drive B
Islamorada, FL 33036
2 bd2 ba1,079 sqft
Listed by Pena Realty, Inc.

All 32 active listings in Islamorada

75090 Overseas Highway
$29,000,000
75090 Overseas Highway
Islamorada, FL 33036
4 bd5.5 ba8,194 sqft
Listed by Ocean Sothebys Intl Realty
82768 Overseas Highway
$25,000,000
82768 Overseas Highway
Islamorada, FL 33036
7 bd10 ba8,288 sqft
Listed by Ocean Sothebys Intl Realty
82719 Old Highway
$24,995,000
82719 Old Highway
Islamorada, FL 33036
7 bd10.5 ba10,182 sqft
Listed by Coldwell Banker Realty
81486 Overseas Highway
$22,500,000
81486 Overseas Highway
Islamorada, FL 33036
7 bd8 ba
Listed by American Caribbean Real Estate
87429 Old Highway
$18,999,000
87429 Old Highway
Islamorada, FL 33036
6 bd8 ba6,692 sqft
Listed by Ocean Sothebys Intl Realty
20 Avacado Street
$15,950,000
20 Avacado Street
Islamorada, FL 33036
6 bd7 ba6,680 sqft
Listed by Beycome of Florida LLC
162 Bayview Drive
$7,950,000
162 Bayview Drive
Islamorada, FL 33036
8 bd9 ba5,392 sqft
Listed by Coldwell Banker Realty
1101 Mastic Street
$6,999,000
1101 Mastic Street
Islamorada, FL 33036
8 bd6 ba3,649 sqft
Listed by LoKation
137 Sapodilla Drive
$5,999,999
137 Sapodilla Drive
Islamorada, FL 33036
5 bd5.5 ba5,456 sqft
Listed by Ocean Sothebys Intl Realty
115 Villa Bella
$4,899,000
115 Villa Bella
Islamorada, FL 33036
4 bd4 ba2,476 sqft
Listed by American Caribbean Real Estate
44 W Plaza Del Lago
$4,750,000
44 W Plaza Del Lago
Islamorada, FL 33036
4 bd4.5 ba4,464 sqft
Listed by Pine River Realty, LLC.
105 Palm Ave.
$4,600,000
105 Palm Ave.
Islamorada, FL 33036
Listed by Paradise Florida Keys Real Est
75761 Overseas Highway
$4,500,000
75761 Overseas Highway
Islamorada, FL 33036
4 bd4 ba3,001 sqft
Listed by Advantage Realty Group, LLC
74049 Overseas Highway
$3,750,000
74049 Overseas Highway
Islamorada, FL 33036
4 bd4 ba2,596 sqft
Listed by Luxe Properties
59 W Plaza Del Sol
$3,275,000
59 W Plaza Del Sol
Islamorada, FL 33036
5 bd3 ba2,922 sqft
Listed by Pine River Realty, LLC.
74560 Overseas Highway
$3,150,000
74560 Overseas Highway
Islamorada, FL 33036
3 ba
Listed by Coldwell Banker Schmitt Real E
80902 OLD Highway
$2,950,000
80902 OLD Highway
Islamorada, FL 33036
4 bd3 ba3,550 sqft
Listed by Coldwell Banker Schmitt Real E
122 Court Contessa
$2,750,000
122 Court Contessa
Islamorada, FL 33036
3 bd3 ba2,374 sqft
Listed by The Keyes Company
122 Court Contessa
$2,740,000
122 Court Contessa
Islamorada, FL 33036
3 bd3.5 ba2,374 sqft
Listed by The Keyes Company
316 N Dr
$2,400,000
316 N Dr
Islamorada, FL 33036
3 bd3.5 ba
Listed by RE/MAX Advance Realty II
316 N Dr
$2,350,000
316 N Dr
Islamorada, FL 33036
3 bd3.5 ba
Listed by RE/MAX Advance Realty II
82891 Overseas Highway
$2,100,000
82891 Overseas Highway
Islamorada, FL
Listed by Keys Properties of the PB's
161 Palermo Drive
$1,950,000
161 Palermo Drive
Islamorada, FL 33036
3 bd2 ba1,190 sqft
Listed by Engel & Völkers Islamorada
133 Anglers Way
$1,700,000
133 Anglers Way
Islamorada, FL 33036
2 bd2.5 ba1,170 sqft
Listed by Douglas Elliman

Listing data comes from the participating MLS and is provided for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Properties shown may be listed by brokerages other than Pure Equity Realty LLC, and are marked with the listing office’s name. Information is deemed reliable but is not guaranteed accurate by the MLS or by Pure Equity Realty LLC, and should be independently verified. Data last updated October 16, 2026.

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