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Luxury Homes in Islamorada, FL

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Luxury Homes in Islamorada, FL

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13 of 114 Listings

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13 of 114 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

62Active
$3,200,000
4 bd · 4 ba · 3,715 sqft
131 Ojibway Ave, Islamorada, FL
Yelisa Mederos · Golden International Realty Corp
13Active
$2,450,000
4 bd · 4 ba · 1,800 sqft
179 Azalea St, Islamorada, FL
Edward Verdeja · Classic Investments Corp.
76Active
$3,275,000
5 bd · 3 ba · 2,922 sqft
59 W Plaza Del Sol, Islamorada, FL
Dominic Rivera · Pine River Realty, LLC.

33Active
$1,700,000
2 bd · 3 ba · 1,170 sqft
133 Anglers Way, Islamorada, FL
Amanda Talbott · Douglas Elliman
Open house Thu, Nov 5 · 11:00 AM62Active
$2,950,000
4 bd · 3 ba · 3,550 sqft
80902 Old Highway, Islamorada, FL
Caroline Hendrix · Coldwell Banker Schmitt Real E
44Active
$1,199,999
2 bd · 3 ba · 1,376 sqft
111 Anglers Way, Islamorada, FL
Scott J Ofstein · Berkshire Hathaway HomeService
77Active
$4,899,000
4 bd · 4 ba · 2,476 sqft
115 Villa Bella, Islamorada, FL
Brooke Vega · American Caribbean Real Estate
Price Reduced100Active
$18,499,000
6 bd · 8 ba · 6,692 sqft
87429 Old Hwy, Islamorada, FL
Michaela Walters · Ocean Sothebys Intl Realty
30Active
$1,950,000
3 bd · 2 ba · 1,190 sqft
161 Palermo Dr, Islamorada, FL
K Shylon Martin · Engel & Völkers Islamorada
39Active
$3,999,999
4 bd · 4 ba · 2,873 sqft
101 Buena Vista Court, Islamorada, FL
Isabella Medlin · Keller Williams Key West Compass Realty
64Active
$24,995,000
7 bd · 11 ba · 10,182 sqft
82719 Old Hwy, Islamorada, FL
Pamela DiMartino · Coldwell Banker Realty
67Active
$2,290,000
4 bd · 3 ba · 2,464 sqft
81250 Overseas Highway Unit 5, Islamorada, FL
AJ Vetter · Palm House Real Estate
55Active
$3,999,000
4 bd · 4 ba · 2,624 sqft
75433 Overseas Highway, Islamorada, FL
Kelsey Caputo - Frins · Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

1 2…5

Listing data & MLS disclosures

Key West Association of REALTORS: The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of The Key West Association of REALTORS®. MLS Real Estate listings held by brokerage firms other than this broker are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker's logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. Information deemed reliable but not guaranteed. Copyright ©2026 The Key West Association of REALTORS®. All Rights Reserved.
MiamiSouthFlorida: Listing information provided by MiamiSouthFlorida.

About Luxury Homes in Islamorada, FL

Luxury Homes in Islamorada, FL: 114 active listings as of November 3, 2026, 02:03 UTC.

Islamorada housing market

September 2026 · This period is still settling

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 24, 2026

Median home size: 3,076 sq. ft.

Islamorada, FL community profile

Area: 54.6 sq. mi.

Source: HJN community data

Explore Islamorada homes

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

Key West Association of REALTORS: The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of The Key West Association of REALTORS®. MLS Real Estate listings held by brokerage firms other than this broker are marked with the MLS logo and detailed information about them includes the name of the listing broker's office. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker's logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. Information deemed reliable but not guaranteed. Copyright ©2026 The Key West Association of REALTORS®. All Rights Reserved.
MiamiSouthFlorida: Listing information provided by MiamiSouthFlorida.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Islamorada, FL community profile

Area: 54.6 sq. mi.

Source: HJN community data

Islamorada housing market

September 2026 · This period is still settling

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 24, 2026

Median home size: 3,076 sq. ft.