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21540 21470 Overseas Highway
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Details for 21540 21470 Overseas Highway, Cudjoe, FL 33042
Multi-Family
  1. Price: $14,495,000.00
  2. Days On Market: 550
  3. Bedrooms: 31
  4. Baths: 19
  5. Acreage: 3.50 acres
  6. Pool: Yes
  7. Waterfront: Yes
  8. Waterfront Type: Oceanfront,Open Water,Bay Front
  9. Year Built: 1958
MLS#: 610484
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Sacarma (21.0)
  5. Provided by: Select Properties of NWFL
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden doc
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785 Sawyer Drive
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Details for 785 Sawyer Drive, Cudjoe, FL 33042
Single Family
  1. Price: $12,900,000.00
  2. Price sqft: $2,994.43 / sqft
  3. Days On Market: 313
  4. Bedrooms: 7
  5. Baths: 6
  6. Bldg sqft: 4308
  7. Acreage: 0.92 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront,Open Water,Canal Front
  11. Year Built: 2019
MLS#: 613645
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cudjoe Gardens (21.0)
  5. Provided by: Coldwell Banker Schmitt Lower Keys (KW)
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Welcome to Cypress Point, an exceptional and highly private oceanfront estate on almost 1 acre on Cudjoe Key, where luxury and coastal beauty seamlessly blend. Behind a private electric gate, this 7 B
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1083 Labat Lane
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Details for 1083 Labat Lane, Cudjoe, FL 33042
Single Family
  1. Price: $5,595,000.00
  2. Price sqft: $2,437.91 / sqft
  3. Days On Market: 574
  4. Bedrooms: 3
  5. Baths: 3
  6. Bldg sqft: 2295
  7. Acreage: 0.09 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront,Open Water
  11. Year Built: 1992
MLS#: 610164
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cutthroat Harbor Est (23.0)
  5. Provided by: Coldwell Banker Schmitt RE Co. Lower Keys Office
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Perched on the oceanfront, this extraordinary Cudjoe Key estate boasts breathtaking views from every vantage point, including the rooftop deck. The solid concrete construction, complete with impact re
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20816 4th Avenue
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Details for 20816 4th Avenue, Cudjoe, FL 33042
Single Family
  1. Price: $4,799,000.00
  2. Price sqft: $1,257.27 / sqft
  3. Days On Market: 378
  4. Bedrooms: 4
  5. Baths: 4
  6. Bldg sqft: 3817
  7. Acreage: 0.38 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Canal Front
  11. Year Built: 2021
MLS#: 612598
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cudjoe Gardens (21.0)
  5. Provided by: Berkshire Hathaway Knight & Gardner
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Exquisite Waterfront Estate in the exclusive Cudjoe GardensWelcome to 20816 4th Ave W, A masterpiece blending luxurious design with the serene beauty of the Florida Keys. Built on a sprawling waterfro
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22572 Jolly Roger Drive
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Details for 22572 Jolly Roger Drive, Cudjoe, FL 33042
Single Family
  1. Price: $3,999,000.00
  2. Price sqft: $1,240.00 / sqft
  3. Days On Market: 652
  4. Bedrooms: 6
  5. Baths: 4
  6. Bldg sqft: 3225
  7. Acreage: 0.33 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Waterfront Type: Oceanfront,Open Water
  11. Year Built: 1963
MLS#: 609116
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cutthroat Harbor Est (23.0)
  5. Provided by: Coldwell Banker Schmitt RE Co. Lower Keys Office
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
A luxury waterfront estate with panoramic ocean views, this walled and gated masterpiece surrounded by gorgeous landscaping provides utmost privacy and the perfect Keys lifestyle and comes completely
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225 Colson Drive
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Details for 225 Colson Drive, Cudjoe, FL 33042
Single Family
  1. Price: $3,995,000.00
  2. Price sqft: $802.85 / sqft
  3. Bedrooms: 6
  4. Baths: 7
  5. Bldg sqft: 4976
  6. Acreage: 1.49 acres
  7. Pool: No
  8. Waterfront: Yes
  9. Waterfront Type: Oceanfront,Open Water
  10. Year Built: 2010
MLS#: 603305
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cudjoe Acres (21.5)
  5. Provided by: Coldwell Banker Schmitt Real Estate Co. (KW)
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
Welcome to your dream Florida Keys oasis! This stunning open water home is a luxurious waterfront retreat, offering the epitome of elegance and comfort. With 6 bedrooms and 6 bathrooms, this spacious
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755 Sawyer Drive
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Details for 755 Sawyer Drive, Cudjoe, FL 33042
Single Family
  1. Price: $3,750,000.00
  2. Price sqft: $2,025.93 / sqft
  3. Previous Price: $274,900
  4. Last Price Change: 12/07/25
  5. Days On Market: 27
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1851
  9. Acreage: 0.41 acres
  10. Pool: No
  11. Waterfront: Yes
  12. Waterfront Type: Oceanfront,Canal Front
  13. Year Built: 1968
MLS#: 617442
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cudjoe Gardens (21.0)
  5. Provided by: Ocean Sotheby's International Realty
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping buttonwoods in the
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755 & 744 Sawyer Drive
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Details for 755 & 744 Sawyer Drive, Cudjoe, FL 33042
Single Family
  1. Price: $3,750,000.00
  2. Price sqft: $2,025.93 / sqft
  3. Previous Price: $49,900
  4. Last Price Change: 09/17/25
  5. Days On Market: 47
  6. Bedrooms: 3
  7. Baths: 2
  8. Bldg sqft: 1851
  9. Acreage: 0.23 acres
  10. Pool: No
  11. Waterfront: Yes
  12. Waterfront Type: Oceanfront
  13. Year Built: 1968
MLS#: 617183
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cudjoe Gardens (21.0)
  5. Provided by: Ocean Sotheby's International Realty
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
In prestigious Cudjoe Gardens, this fully renovated Keys retreat feels more like a private sanctuary than a house. The main oceanfront lot is wrapped in lush, mature landscaping buttonwoods in the
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22815 Port Royal Lane
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Details for 22815 Port Royal Lane, Cudjoe, FL 33042
Single Family
  1. Price: $3,750,000.00
  2. Price sqft: $1,161.71 / sqft
  3. Days On Market: 131
  4. Bedrooms: 4
  5. Baths: 5
  6. Bldg sqft: 3228
  7. Acreage: 0.38 acres
  8. Pool: No
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Oceanfront,Open Water,Canal Front,Bay Front
  12. Year Built: 2013
MLS#: 616122
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cutthroat Harbor Est (23.0)
  5. Provided by: Gailey Enterprises Real Estate
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
DIRECT OCEAN FRONT 323FT of Water Frontage BOATERS PARADISE FOUND with room for 3 Boats on unobstructed sunset view over open water oversized corner lot with water on 2 sides at end of a private ro
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22815 Port Royal Lane
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Details for 22815 Port Royal Lane, Cudjoe, FL 33042
Single Family
  1. Price: $3,750,000.00
  2. Price sqft: $1,161.71 / sqft
  3. Days On Market: 217
  4. Bedrooms: 4
  5. Baths: 3
  6. Bldg sqft: 3228
  7. Acreage: 0.38 acres
  8. Pool: No
  9. Spa/HotTub: Yes
  10. Waterfront: Yes
  11. Waterfront Type: Oceanfront,Open Water,Canal Front,Bay Front
  12. Year Built: 1995
MLS#: 615074
  1. County: MONROE
  2. City: Cudjoe
  3. Zipcode: 33042
  4. Subdivision: Cutthroat Harbor Est (23.0)
  5. Provided by: Gailey Enterprises Real Estate
  6. Florida Keys Board of REALTORS
  7. DMCA Notice
BOATERS PARADISE FOUND with an unobstructed sunset view over open water year round on oversized corner lot with water on 2 sides at the very end of a private road offering picture perfect sunsets in a
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