Searching on:
  1. City = Islamorada
100 Sandy Cove Avenue
More Like This
Details for 100 Sandy Cove Avenue, ISLAMORADA, FL 33036
Land
  1. Price: $57,500,000.00
  2. Acreage: 0.00 acres
  3. Pool: No
  4. Waterfront: Yes
  5. Waterfront Type: Bay Front
  6. Year Built: Not Available
MLS#: 610143
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Misc Lower Matacumbe (76.0)
  5. Provided by: Coastal Realty of the Florida Keys
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Discover a unique opportunity with this exceptional parcel of land, featuring extensive waterfront views and includes 9 TDR's. This prime property offers natural beauty, and the ability to develop one
Listing Details and 18 Additional Pictures
Request more information about this listing.
88041 Old Highway
Virtual Tour
More Like This
Details for 88041 Old Highway, ISLAMORADA, FL 33036
Single Family
  1. Price: $42,000,000.00
  2. Price sqft: $4,266.99 / sqft
  3. Days On Market: 203
  4. Bedrooms: 6
  5. Baths: 9
  6. Bldg sqft: 9843
  7. Acreage: 5.07 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Oceanfront,Salt Ponds,Lake Front,Open Water
  12. Year Built: 2017
MLS#: 613646
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Plant Beach (87.5)
  5. Provided by: Ocean Sotheby's International Realty
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
An exquisite masterpiece of coastal luxury crafted by visionaries to create the ultimate secluded paradise. This architectural gem, designed by the renowned Siskind architects Bruce Carlson and Steve
Listing Details and 182 Additional Pictures
Request more information about this listing.
76180 Overseas Highway
Virtual Tour
More Like This
Details for 76180 Overseas Highway, ISLAMORADA, FL 33036
Single Family
  1. Price: $31,200,000.00
  2. Price sqft: $3,050.45 / sqft
  3. Days On Market: 93
  4. Bedrooms: 8
  5. Baths: 10
  6. Bldg sqft: 10228
  7. Acreage: 1.65 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Bay Front,Open Water,Gulf Front
  12. Year Built: 2024
MLS#: 615275
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Misc Lower Matacumbe (76.0)
  5. Provided by: Ocean Sotheby's International Realty
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Spectacular 1.65 Acre Bayfront Estate in Islamorada, Florida Keys |
8 Bedrooms | 9.5 Bathrooms | 10,228 Total Sq Ft | 150' Waterfront | Dockage | Pool | BeachWelcome to a rare offering in the he
Listing Details and 183 Additional Pictures
Request more information about this listing.
82719 Old Highway
Virtual Tour
More Like This
Details for 82719 Old Highway, Islamorada, FL 33036
Single Family
  1. Price: $29,500,000.00
  2. Days On Market: 181
  3. Bedrooms: 7
  4. Baths: 7
  5. Garage / Parking Spaces: 5
  6. Acreage: 0.86 acres
  7. Pool: Yes
  8. Community Pool: Yes
  9. Waterfront: Yes
  10. Wateraccess: Yes
  11. Year Built: 1995
MLS#: RX-11068201
  1. County: MONROE
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Strattons Subd
  5. Provided by: Serhant
  6. Provided through
  7. DMCA Notice
Showcasing an oasis of distinguished elegance and prime coastal beach charm, this extraordinary property spans over 40,000 square feet of exquisite indoor and outdoor living spaces. It masterfully com
Listing Details and 146 Additional Pictures
Request more information about this listing.
82719 Old Highway
More Like This
Details for 82719 Old Highway, ISLAMORADA, FL 33036
Single Family
  1. Price: $29,500,000.00
  2. Price sqft: $3,398.62 / sqft
  3. Days On Market: 146
  4. Bedrooms: 5
  5. Baths: 10
  6. Bldg sqft: 8680
  7. Acreage: 0.97 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront
  11. Year Built: 1995
MLS#: 614564
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Strattons (82.5)
  5. Provided by: Serhant Florida LLC - Delray Beach Office
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Listing Details and 128 Additional Pictures
Request more information about this listing.
82768 Overseas Highway
Virtual Tour
More Like This
Details for 82768 Overseas Highway, ISLAMORADA, FL 33036
Single Family
  1. Price: $25,000,000.00
  2. Price sqft: $3,604.90 / sqft
  3. Days On Market: 228
  4. Bedrooms: 7
  5. Baths: 10
  6. Bldg sqft: 6935
  7. Acreage: 3.37 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Bay Front,Open Water,Gulf Front
  12. Year Built: 2017
MLS#: 613195
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Russell Estates (83.2)
  5. Provided by: Ocean Sotheby's International Realty
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Welcome to Serenity Cay, an exquisite Balinese inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling wat
Listing Details and 138 Additional Pictures
Request more information about this listing.
82768 Overseas Highway
More Like This
Details for 82768 Overseas Highway, ISLAMORADA, FL 33036
Single Family
  1. Price: $25,000,000.00
  2. Price sqft: $3,016.41 / sqft
  3. Days On Market: 614
  4. Bedrooms: 7
  5. Baths: 9
  6. Bldg sqft: 8288
  7. Acreage: 3.37 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Bay Front,Open Water
  12. Year Built: 2017
MLS#: 607949
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Russell Estates (83.2)
  5. Provided by: American Caribbean Real Estate, Christie's Interna
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
SERENITY CAY is an unparalleled and extraordinary estate nestled in the heart of Islamorada. This exclusive 3.37 acre compound offers utmost privacy with its gated and fenced entrance. As you enter th
Listing Details and 139 Additional Pictures
Request more information about this listing.
141 Cortez Drive
" target="_blank" title="Click to View Virtual Tour of this Property">Virtual Tour
More Like This
Details for 141 Cortez Drive, ISLAMORADA, FL 33036
Single Family
  1. Price: $25,000,000.00
  2. Price sqft: $6,627.78 / sqft
  3. Previous Price: $2,698,900
  4. Last Price Change: 08/17/25
  5. Days On Market: 943
  6. Bedrooms: 10
  7. Baths: 11
  8. Bldg sqft: 3772
  9. Acreage: 16.45 acres
  10. Pool: Yes
  11. Waterfront: Yes
  12. Waterfront Type: Oceanfront,Open Water,Canal Front
  13. Year Built: 2002
MLS#: 604054
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Matecumbe Ocean Bay (75.0)
  5. Provided by: Ocean Sotheby's International Realty
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Live like you're in the movies! Bask in the original elements of the Florida Keys way of life at Kids Cay. Now being offered for the very first time, this one of a kind legacy property boasts three ch
Listing Details and 103 Additional Pictures
Request more information about this listing.
88351 Old Highway
More Like This
Details for 88351 Old Highway, ISLAMORADA, FL 33036
Single Family
  1. Price: $20,995,000.00
  2. Price sqft: $2,713.23 / sqft
  3. Days On Market: 35
  4. Bedrooms: 6
  5. Baths: 9
  6. Bldg sqft: 7738
  7. Acreage: 2.04 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Oceanfront,Open Water
  12. Year Built: 2025
MLS#: 615973
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Pearl City (89.0)
  5. Provided by: Coldwell Banker Schmitt Islamorada
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
'Tranquility Haven' features the newest construction in Islamorada... completed January 2025! As you enter the gated and fenced sanctuary a long winding driveway leads up to an elevated entrance and c
Listing Details and 56 Additional Pictures
Request more information about this listing.
88351 Old Highway
More Like This
Details for 88351 Old Highway, ISLAMORADA, FL 33036
Single Family
  1. Price: $20,995,000.00
  2. Price sqft: $3,022.60 / sqft
  3. Days On Market: 217
  4. Bedrooms: 6
  5. Baths: 9
  6. Bldg sqft: 6946
  7. Acreage: 2.04 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Oceanfront,Open Water
  12. Year Built: 2025
MLS#: 613376
  1. County: MONROE
  2. City: ISLAMORADA
  3. Zipcode: 33036
  4. Subdivision: Pearl City (89.0)
  5. Provided by: Coldwell Banker Schmitt Islamorada
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
'Tranquility Haven' features the newest construction in Islamorada... completed January 2025! As you enter the gated and fenced sanctuary a long winding driveway leads up to an elevated entrance and c
Listing Details and 31 Additional Pictures
Request more information about this listing.