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  1. City = Islamorada
  2. Listing Status = Active
77340 Overseas Highway
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Details for 77340 Overseas Highway, Islamorada, FL 33036
Single Family
  1. Price: $3,999,999.00
  2. Price sqft: $2,081.17 / sqft
  3. Days On Market: 6
  4. Bedrooms: 2
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 1922
  8. Acreage: 0.79 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1963
MLS#: B26001957
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Matecumbe Ocean Bay Sec 2
  5. Elementary School: Plantation Key
  6. Middle School: Plantation Key
  7. High School: Coral Shores
  8. Provided by: Coldwell Banker Schmitt RE Co
  9. Provided through
  10. DMCA Notice
Estate Opportunity Spanning 34,409 SF, this exceptional parcel offers a scale uncommon in Islamorada, providing the foundation for a spectacular Florida Keys residential estate. The exceptional lot
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439 Palm Dr Drive
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Details for 439 Palm Dr Drive, Islamorada, FL 33036
Single Family
  1. Price: $2,495,000.00
  2. Price sqft: $1,087.62 / sqft
  3. Previous Price: $2,650,000
  4. Last Price Change: 02/28/26
  5. Days On Market: 84
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 4
  9. Bldg sqft: 2294
  10. Acreage: 0.25 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1983
MLS#: R11149737
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Safety Harbor
  5. Elementary School: Plantation Key
  6. High School: Coral Shores
  7. Provided by: Coldwell Banker Schmitt RE Co
  8. Provided through
  9. DMCA Notice
VA assumable! Experience refined waterfront living in the Florida Keys, where luxury meets effortless access to world class boating and fishing. This exceptional canal front residence is thoughtfully
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143 Hammock Road
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Details for 143 Hammock Road, ISLAMORADA, FL 33036
Single Family
  1. Price: $1,299,000.00
  2. Price sqft: $615.06 / sqft
  3. Days On Market: 34
  4. Bedrooms: 3
  5. Baths: 3
  6. Bldg sqft: 2112
  7. Acreage: 0.27 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 2020
MLS#: TB8476169
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Upper Matecumbe Key
  5. Provided by: COMMERCIAL PROPERTY BROKERS
  6. mfrmls
  7. DMCA Notice
Experience all that Islamorada can provide from this stunning home that was constructed in 2020. This two story residence offers 3 spacious bedrooms and 2 full bathrooms on the ground floor. The secon
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102 Anglers Way
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Details for 102 Anglers Way, Islamorada, FL 33036
Single Family
  1. Price: $1,150,000.00
  2. Days On Market: 59
  3. Bedrooms: 2
  4. Baths: 3
  5. Garage / Parking Spaces: 1
  6. Acreage: 0.00 acres
  7. Pool: No
  8. Waterfront: No
  9. Year Built: 2007
MLS#: F10546467
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Anglers Reef
  5. Elementary School: Plantation Key
  6. Middle School: Plantation Key
  7. High School: Coral Shores
  8. Provided by: Berkshire Hathaway Florida Realty
  9. Provided through
  10. DMCA Notice
ANGLERS REEF HOME THAT PAYS FOR ITSELF! Islamorada's Upscale Oceanfront Gated Community that allows Vacation Rentals, This home features 2 bedrooms, 2.5 bathrooms with carport & 4 porches. Upgrades in
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219 Preston Street
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Details for 219 Preston Street, Islamorada, FL 33036
Single Family
  1. Price: $895,000.00
  2. Price sqft: $506.80 / sqft
  3. Previous Price: $990,000
  4. Last Price Change: 02/28/26
  5. Days On Market: 100
  6. Bedrooms: 4
  7. Baths: 2
  8. Bldg sqft: 1766
  9. Acreage: 0.19 acres
  10. Pool: No
  11. Waterfront: No
  12. Year Built: 1934
MLS#: R11146822
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Matecumbe Beach (mm 82)
  5. Elementary School: Plantation Key
  6. Middle School: Plantation Key
  7. High School: Coral Shores
  8. Provided by: Coldwell Banker Schmitt RE Co
  9. Provided through
  10. DMCA Notice
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Tropic Shores Realty - Crystal River
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Listing Data ©2026 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on March 20, 2026 @ 12:00 am
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