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Details for 75090 Overseas Highway, Islamorada, FL 33036
Single Family
  1. Price: $29,000,000.00
  2. Days On Market: 63
  3. Bedrooms: 4
  4. Baths: 6
  5. Garage / Parking Spaces: 6
  6. Acreage: 1.00 acres
  7. Pool: Yes
  8. Waterfront: No
  9. Year Built: 2011
MLS#: A12050889
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Matecumbe Ocean Bay (75.0)
  5. Elementary School: Plantation Key
  6. High School: Coral Shores
  7. Provided by: Ocean Sothebys Intl Realty
  8. Provided through
  9. DMCA Notice
Villa Lago is an Italian inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre of bayfront property, a dramat
Details for 82768 Overseas Highway, Islamorada, FL 33036
Single Family
  1. Price: $25,000,000.00
  2. Days On Market: 98
  3. Bedrooms: 7
  4. Baths: 10
  5. Garage / Parking Spaces: 4
  6. Acreage: 0.00 acres
  7. Pool: Yes
  8. Waterfront: No
  9. Year Built: 2017
MLS#: A12022973
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Islamorada
  5. Elementary School: Plantation Key
  6. Middle School: Plantation Key
  7. High School: Coral Shores
  8. Provided by: Ocean Sothebys Intl Realty
  9. Provided through
  10. 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
Details for Address Not Provided
Single Family
  1. Price: $22,500,000.00
  2. Days On Market: 201
  3. Bedrooms: 7
  4. Baths: 9
  5. Garage / Parking Spaces: 3
  6. Acreage: 0.00 acres
  7. Pool: Yes
  8. Waterfront: No
  9. Year Built: 2026
MLS#: A11962802
  1. County: MONROE
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Upper Matecumbe
  5. Provided by: American Caribbean Real Estate
  6. Provided through
  7. DMCA Notice
Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla
Details for 87429 Old Highway, Islamorada, FL 33036
Single Family
  1. Price: $18,999,000.00
  2. Price sqft: $1,024.26 / sqft
  3. Previous Price: $19,500,000
  4. Last Price Change: 06/26/26
  5. Days On Market: 152
  6. Bedrooms: 6
  7. Baths: 6
  8. Garage / Parking Spaces: 8
  9. Bldg sqft: 18549
  10. Acreage: 3.00 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2022
MLS#: A11990479
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Plantation Beach
  5. Elementary School: Plantation Key
  6. Middle School: Plantation Key
  7. High School: Coral Shores
  8. Provided by: Ocean Sothebys Intl Realty
  9. Provided through
  10. DMCA Notice
A private sanctuary of coastal sophistication, The Oasis offers two residences spanning 2.85 meticulously landscaped acres with over 400 feet of pristine waterfront and a protected deepwater basin. De
Details for 20 Avacado Street, Islamorada, FL 33036
Single Family
  1. Price: $15,950,000.00
  2. Price sqft: $1,295.17 / sqft
  3. Days On Market: 182
  4. Bedrooms: 6
  5. Baths: 7
  6. Bldg sqft: 12315
  7. Acreage: 2.00 acres
  8. Pool: Yes
  9. Waterfront: No
  10. Year Built: 2005
MLS#: A11972240
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Islamorada, Townsite Of
  5. Elementary School: Plantation Key
  6. Middle School: Plantation Key
  7. High School: Coral Shores
  8. Provided by: Beycome of Florida LLC
  9. Provided through
  10. DMCA Notice
BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWSWelcome to one of Islamorada's premier rare bayside estate properties a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The
Details for 75840 Overseas Highway, Islamorada, FL 33036
Single Family
  1. Price: $13,250,000.00
  2. Previous Price: $13,500,000
  3. Last Price Change: 08/06/26
  4. Days On Market: 117
  5. Bedrooms: 7
  6. Baths: 7
  7. Garage / Parking Spaces: 4
  8. Acreage: 2.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: A12017379
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Mat Ocean Bay
  5. Elementary School: Plantation Key
  6. Middle School: Plantation Key
  7. High School: Coral Shores
  8. Provided by: Langley Knight Gardner Islamorada
  9. Provided through
  10. DMCA Notice
LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pristine bayfront offering deep w
Details for 77350 Overseas Highway, Islamorada, FL 33036
Single Family
  1. Price: $11,700,000.00
  2. Price sqft: $1,143.92 / sqft
  3. Days On Market: 39
  4. Bedrooms: 6
  5. Baths: 8
  6. Garage / Parking Spaces: 4
  7. Bldg sqft: 10228
  8. Acreage: 1.00 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 2025
MLS#: A12056007
  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: American Caribbean Real Estate
  9. Provided through
  10. DMCA Notice
Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a serene coastal landscape and na
Details for 162 Bayview Drive, Islamorada, FL 33036
Single Family
  1. Price: $8,590,000.00
  2. Price sqft: $816.70 / sqft
  3. Previous Price: $8,950,000
  4. Last Price Change: 07/04/26
  5. Days On Market: 471
  6. Bedrooms: 8
  7. Baths: 10
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 10518
  10. Acreage: 0.00 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 2014
MLS#: A11800398
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Safety Harbor Sec 1
  5. Elementary School: Plantation Key
  6. High School: Coral Shores
  7. Provided by: Coldwell Banker Realty
  8. Provided through
  9. DMCA Notice
Nestled in the Safety Harbor enclave, Islamorada, this stunning Gulfside estate offers unparalleled blend of luxury and tranquility. Situated on a prime point w/open water and protected dockage, makes
Details for 1101 Mastic Street, Islamorada, FL 33036
Single Family
  1. Price: $6,999,000.00
  2. Price sqft: $291.58 / sqft
  3. Previous Price: $7,495,000
  4. Last Price Change: 07/22/26
  5. Days On Market: 120
  6. Bedrooms: 8
  7. Baths: 6
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 24004
  10. Acreage: 0.00 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1984
MLS#: A12009440
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Strattons Subdivision Pb2
  5. Elementary School: Plantation Key
  6. High School: Coral Shores
  7. Provided by: LoKation
  8. Provided through
  9. DMCA Notice
Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available.Experience luxury coastal living at its finest in this exceptional Gated ba
Details for 88110 Overseas Highway, Islamorada, FL 33036
Single Family
  1. Price: $6,999,000.00
  2. Price sqft: $1,081.76 / sqft
  3. Days On Market: 112
  4. Bedrooms: 4
  5. Baths: 5
  6. Bldg sqft: 6470
  7. Acreage: 1.00 acres
  8. Pool: No
  9. Waterfront: No
  10. Year Built: 1957
MLS#: A12032087
  1. County: Monroe
  2. City: Islamorada
  3. Zipcode: 33036
  4. Subdivision: Plantation Beach
  5. Elementary School: Plantation Key
  6. High School: Coral Shores
  7. Provided by: Langley Knight Gardner Islamorada
  8. Provided through
  9. DMCA Notice
Private Bayfront Estate in desirable Islamorada offering a serene ambiance on an oversized parcel of pristine bayfront with breathtaking sunsets and unobstructed panoramic views of the Florida Bay. Th