Waterfront - Windley Key Islamorada Waterfront Homes
41 results
- 82768 Overseas Hwy, Islamorada, FL 33036
- 7 bds
- 10 ba
- 6,935 sqft
OCEAN SOTHEBY'S INTERNATIONAL REALTY Loading...
- 84961 Old Hwy Lot 18, Windley Key, FL 33036
- 2 bds
- 2 ba
- 793 sqft
BERKSHIRE HATHAWAY HOMESERVICES KEYS REAL ESTATE - ISLAMORADA - 124 Venetian Way, Plantation Key, FL 33036
- 4 bds
- 3 ba
- 2,096 sqft
BERKSHIRE HATHAWAY HOMESERVICES KEYS REAL ESTATE - ISLAMORADA - 100 List St, Islamorada, FL 33036
- 3 bds
- 3 ba
- 3,019 sqft
COLDWELL BANKER SCHMITT ISLAMORADA - 153 Stromboli Dr, Plantation Key, FL 33036
- 6 bds
- 5 ba
- 4,964 sqft
BERKSHIRE HATHAWAY HOMESERVICES KEYS REAL ESTATE - ISLAMORADA - 120 Toner Ln, Plantation Key, FL 33036
- 4 bds
- 4 ba
- 3,052 sqft
OCEAN SOTHEBY'S INTERNATIONAL REALTY Loading...
- 87200 Overseas Hwy APT M2, Plantation Key, FL 33036
- 4 bds
- 2 ba
- 1,354 sqft
ANCHOR REALTY OF FL, LLC - 82779 Old Hwy #14, Islamorada, FL 33036
- 4 bds
- 5 ba
- 2,574 sqft
OCEAN SOTHEBY'S INTERNATIONAL REALTY - 84961 Old Hwy Lot 21, Windley Key, FL 33036
- 2 bds
- 2 ba
- 946 sqft
BERKSHIRE HATHAWAY HOMESERVICES KEYS REAL ESTATE - ISLAMORADA - 83407 Old Hwy, Islamorada, FL 33036
- 6 bds
- 5 ba
- 4,566 sqft
OCEAN SOTHEBY'S INTERNATIONAL REALTY - 136 Giardino Dr, Plantation Key, FL 33036
- 4 bds
- 3 ba
- 3,481 sqft
COLDWELL BANKER SCHMITT ISLAMORADA - 87200 Overseas Hwy APT V9, Plantation Key, FL 33036
- 3 bds
- 2 ba
- 1,355 sqft
PREMIER PROPERTIES - 106 San Juan Dr, Plantation Key, FL 33036
- 3 bds
- 3 ba
- 2,055 sqft
COLDWELL BANKER SCHMITT ISLAMORADA - 85960 Overseas Hwy, Islamorada, FL 33036
- -- sqft lot
COLDWELL BANKER SCHMITT KEY LARGO - 109 Milano Dr, Plantation Key, FL 33036
- 3 bds
- 3 ba
- 1,368 sqft
COLDWELL BANKER SCHMITT ISLAMORADA - 82749 Old Hwy, Islamorada, FL 33036
- 3 bds
- 3 ba
- 1,485 sqft
COLDWELL BANKER SCHMITT ISLAMORADA - 87200 Overseas Hwy APT O8, Plantation Key, FL 33036
- 2 bds
- 3 ba
- 1,365 sqft
COLDWELL BANKER SCHMITT ISLAMORADA - 84745 Old Hwy #4, Islamorada, FL 33036
- 3 bds
- 3 ba
- 1,680 sqft
AMERICAN CARIBBEAN REAL ESTATE - 105 Palo De Oro Dr, Plantation Key, FL 33036
- 5 bds
- 3 ba
- 2,640 sqft
COLDWELL BANKER SCHMITT ISLAMORADA - 81910 & 81908 Overseas Hwy, Islamorada, FL 33036
- 0.7 acres lot
OCEAN SOTHEBY'S INTERNATIONAL REALTY - 229 Coral Rd, Plantation Key, FL 33036
- 0.48 acres lot
OCEAN SOTHEBY'S INTERNATIONAL REALTY - 87200 Overseas Hwy APT I3, Plantation Key, FL 33036
- 2 bds
- 2 ba
- 1,419 sqft
COASTAL REALTY OF THE FLORIDA KEYS - 83201 Old Hwy APT 301, Upper Matecumbe Key, FL 33036
- 2 bds
- 2 ba
- 1,275 sqft
OCEAN SOTHEBY'S INTERNATIONAL REALTY - 83201 Old Hwy APT 504, Upper Matecumbe Key, FL 33036
- 2 bds
- 2 ba
- 1,275 sqft
PALM HOUSE REAL ESTATE - 128 Leoni Dr, Plantation Key, FL 33036
- 5 bds
- 5 ba
- 3,556 sqft
REAL ESTATE SALES FORCE - CORAL GABLES - 81906 Overseas Hwy #2, Islamorada, FL 33036
- 3 bds
- 4 ba
- 1,829 sqft
OCEAN SOTHEBY'S INTERNATIONAL REALTY - 82900 Old Hwy, Islamorada, FL 33036
- 7.78 acres lot
OCEAN SOTHEBY'S INTERNATIONAL REALTY - 84745 Old Hwy #C1, Windley Key, FL 33036
- 3 bds
- 3 ba
- 1,680 sqft
AMERICAN CARIBBEAN REAL ESTATE, CHRISTIE'S INTERNATIONAL REAL ESTATE - 83201 Old Hwy APT 405, Upper Matecumbe Key, FL 33036
- 2 bds
- 2 ba
- 1,275 sqft
COASTAL REALTY OF THE FLORIDA KEYS - 81906 Overseas Hwy #3, Islamorada, FL 33036
- 3 bds
- 4 ba
- 1,768 sqft
AMERICAN CARIBBEAN REAL ESTATE, CHRISTIE'S INTERNATIONAL REAL ESTATE - 84745 Old Hwy #7, Islamorada, FL 33036
- 3 bds
- 3 ba
- 1,680 sqft
AMERICAN CARIBBEAN REAL ESTATE

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

MLS Internet Data Exchange (IDX) information is provided exclusively for consumersā personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.

The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS. Copyright 2026 Southwest Florida MLS. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
- For Sale
- Florida
- Monroe County
- Islamorada
- Windley Key
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Disclaimer: School attendance zone boundaries are supplied by Pitney Bowes and are subject to change. Check with the applicable school district prior to making a decision based on these boundaries.
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