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15760 Old State Road 4a
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Details for 15760 Old State Road 4a, Sugarloaf, FL 33042
Single Family
  1. Price: $19,750,000.00
  2. Price sqft: $4,486.60 / sqft
  3. Days On Market: 16
  4. Bedrooms: 6
  5. Baths: 7
  6. Bldg sqft: 4402
  7. Acreage: 5.33 acres
  8. Pool: No
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront
  11. Year Built: 1976
MLS#: 617534
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Beach (17.0)
  5. Provided by: The Agency Florida Keys
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Rare Private Sandy Beach Oceanfront Estate with endless open ocean views, just 30 minutes to Key West! This is a once in a lifetime opportunity to own over 5 acres of sprawling oceanfrontage on excl
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1041 Buttonwood Drive
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Details for 1041 Buttonwood Drive, Sugarloaf, FL 33042
Single Family
  1. Price: $11,000,000.00
  2. Price sqft: $2,247.65 / sqft
  3. Previous Price: $258,888
  4. Last Price Change: 12/16/25
  5. Days On Market: 7
  6. Bedrooms: 6
  7. Baths: 8
  8. Bldg sqft: 4894
  9. Acreage: 0.30 acres
  10. Pool: Yes
  11. Spa/HotTub: Yes
  12. Waterfront: Yes
  13. Waterfront Type: Open Water
  14. Year Built: 2025
MLS#: 617664
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Shores (17.0)
  5. Provided by: The Agency Florida Keys
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Masterpiece of Modern Strength & Luxury | Brand New Concrete Waterfront Estate on Prestigious Sugarloaf Key!This extraordinary new construction stunner is engineered as a rare modern fortress built
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15420 Old State Road 4a
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Details for 15420 Old State Road 4a, Sugarloaf, FL 33042
Single Family
  1. Price: $6,900,000.00
  2. Price sqft: $1,530.27 / sqft
  3. Days On Market: 428
  4. Bedrooms: 4
  5. Baths: 4
  6. Bldg sqft: 4509
  7. Acreage: 0.89 acres
  8. Pool: No
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront,Open Water
  11. Year Built: 1996
MLS#: 611828
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Beach (17.0)
  5. Provided by: Coldwell Banker Schmitt Lower Keys (KW)
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Stunning Sugarloaf Beach estate, with Open Water Views, infinity pool, and private, wide sandy beach, surrounded by nature! Currently utilized as a successful vacation rental, where nightly rentals ar
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15420 Old State Rd 4a
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Details for 15420 Old State Rd 4a, Sugarloaf, FL 33042
Single Family
  1. Price: $6,300,000.00
  2. Price sqft: $1,397.21 / sqft
  3. Days On Market: 298
  4. Bedrooms: 4
  5. Baths: 4
  6. Bldg sqft: 4509
  7. Acreage: 1.17 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Oceanfront,Open Water
  12. Year Built: 1996
MLS#: 613841
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Beach (17.0)
  5. Provided by: Coldwell Banker Schmitt Lower Keys (KW)
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Located on beautiful Sugarloaf Beach where nightly rentals are allowed this 1+ acre oceanfront property boasts a gorgeous wide sand beach, oceanfront infinity pool, and endless ocean views! Currently
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16745 Tamarind Road
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Details for 16745 Tamarind Road, Sugarloaf, FL 33042
Single Family
  1. Price: $5,494,000.00
  2. Price sqft: $1,889.92 / sqft
  3. Days On Market: 405
  4. Bedrooms: 4
  5. Baths: 5
  6. Bldg sqft: 2907
  7. Acreage: 0.29 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront,Open Water
  11. Year Built: 2022
MLS#: 612166
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Shores (17.0)
  5. Provided by: Bestway Realty Sales, LLC
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Welcome to your waterfront paradise! This solid concrete, newly built 4 bedroom, 4.5 bath home offers unparalleled luxury finishes and an open floor plan designed for modern coastal living. The chef's
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17129 Amberjack Lane
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Details for 17129 Amberjack Lane, Sugarloaf, FL 33042
Single Family
  1. Price: $5,250,000.00
  2. Price sqft: $1,250.00 / sqft
  3. Days On Market: 510
  4. Bedrooms: 6
  5. Baths: 7
  6. Bldg sqft: 4200
  7. Acreage: 0.29 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Canal Front,Open Water
  11. Year Built: 2023
MLS#: 610889
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Shores (17.0)
  5. Provided by: Ocean Sotheby's International Realty
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Welcome to Sunset Reef, where luxury meets the tranquility of island living. This newly constructed masterpiece offers the ultimate Florida Keys lifestyle, complete with breathtaking sunset views, unp
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16745 Tamarind Road
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Details for 16745 Tamarind Road, Sugarloaf, FL 33042
Single Family
  1. Price: $4,950,000.00
  2. Price sqft: $1,702.79 / sqft
  3. Days On Market: 228
  4. Bedrooms: 4
  5. Baths: 3
  6. Bldg sqft: 2907
  7. Acreage: 0.29 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront,Open Water
  11. Year Built: 2022
MLS#: 614884
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Shores (17.0)
  5. Provided by: Bestway Realty Sales, LLC
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Huge Price Improvement! Welcome to your waterfront paradise! This solid concrete, newly built 4 bedroom, 4.5 bath home offers unparalleled luxury finishes and an open floor plan designed for modern co
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16705 Tamarind Road
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Details for 16705 Tamarind Road, Sugarloaf, FL 33042
Single Family
  1. Price: $4,495,000.00
  2. Price sqft: $1,456.58 / sqft
  3. Days On Market: 489
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 3086
  7. Acreage: 0.44 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Bay Front,Open Water
  11. Year Built: 2015
MLS#: 611101
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Shores (17.0)
  5. Provided by: Berkshire Hathaway Knight & Gardner
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Exquisite Open Water Estate on Prestigious Southpoint, Sugarloaf Key! Experience unparalleled luxury at this stunning solid concrete open water property, located just 20 minutes from the magic of Key
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16745 Tamarind Road
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Details for 16745 Tamarind Road, Sugarloaf, FL 33042
Single Family
  1. Price: $4,400,000.00
  2. Price sqft: $1,513.59 / sqft
  3. Days On Market: 16
  4. Bedrooms: 4
  5. Baths: 5
  6. Bldg sqft: 2907
  7. Acreage: 0.29 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Open Water
  11. Year Built: 2022
MLS#: 617539
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Shores (17.0)
  5. Provided by: American Caribbean Real Estate, Christie's Intern
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Step into your own waterfront sanctuary, where clean, modern design meets unmistakable Florida Keys ease. This beautifully built CBS home delivers 4 spacious bedrooms and 4.5 baths, wrapped in contemp
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17018 Wahoo Lane
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Details for 17018 Wahoo Lane, Sugarloaf, FL 33042
Single Family
  1. Price: $3,874,900.00
  2. Price sqft: $2,632.40 / sqft
  3. Days On Market: 341
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 1472
  7. Acreage: 0.30 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Oceanfront,Open Water,Canal Front
  12. Year Built: 1991
MLS#: 613068
  1. County: MONROE
  2. City: Sugarloaf
  3. Zipcode: 33042
  4. Subdivision: Sugarloaf Shores (17.0)
  5. Provided by: Expert Realty LLC (HQ)
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Welcome to the most exceptional home and premier lot currently available in the prestigious Sugarloaf Shores neighborhood. This property is a masterpiece of luxury, craftsmanship, and natural beauty,
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