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Luxury Homes in Islamorada, FL

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Luxury Homes in Islamorada, FL

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22 of 91 Listings

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22 of 91 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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

62Active
$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
100Active
$18,999,000
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
69Active
$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 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
24Active
$1,600,000
3 bd · 2 ba · 1,380 sqft
102 Venetian Dr, Islamorada, FL
Arelys Doger-Sanchez · Keller Williams Realty Premier Properties
Price Reduced52Active
$2,500,000
3 bd · 3 ba · 1,632 sqft
107 Valencia Drive, Islamorada, FL
Patty Accorto · Keller Williams Legacy
55Active
$3,952,000
5 bd · 3 ba · 2,328 sqft
148 Giardino Drive, Islamorada, FL
Oscar Valencia · The Valencia Group Corp.
Price Reduced45Active
$2,350,000
3 bd · 4 ba · — sqft
316 N Dr, Islamorada, FL
Anthony Askowitz · RE/MAX Advance Realty II
49Active
$3,700,000
3 bd · 3 ba · 1,729 sqft
313 North Drive, Islamorada, FL
Sharon Kelly-Brown · Sharon J. Kelly Realty, Inc.
80Active
$2,740,000
3 bd · 4 ba · 2,374 sqft
122 Court Contessa, Islamorada, FL
Lourdes Martin-Rosa · The Keyes Company
69Active
$6,195,000
4 bd · 5 ba · 3,284 sqft
144 N Rolling Hill Road, Islamorada, FL
Karan Moeller, PA · Ocean Sotheby's International Realty
59Active
$2,000,000
3 bd · 3 ba · 1,771 sqft
155 Plantation Avenue, Islamorada, FL
Seanna Lindback Porter · Sea Haven Realty, Inc.
134Active
$11,000,000
5 bd · 5 ba · 3,421 sqft
75751 Overseas Highway, Islamorada, FL
Lisa Frins P.A. · Berkshire Hathaway HomeServices Keys Real Estate - Islamorada
80Active
$4,750,000
4 bd · 5 ba · 2,574 sqft
82779 Old Highway 1, Islamorada, FL
Sabrina Wampler & Sarah Ewald · Ocean Sotheby's International Realty

1 2…4

Listing data & MLS disclosures

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. 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.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-10-09 05:55:25 UTC
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.
MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-10-15 06:07:49 UTC

About Luxury Homes in Islamorada, FL

Luxury Homes in Islamorada, FL: 91 active listings as of October 15, 2026, 09:12 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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Homes Over $3M

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

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. 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.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-10-09 05:55:25 UTC
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.
MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-10-15 06:07:49 UTC

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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Realty.com

Lic. #BK3453168

Call Thomas