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  1. Subdivision Like Siesta Isles
5569 Cape Leyte Drive
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Details for 5569 Cape Leyte Drive, SARASOTA, FL 34242
Single Family
  1. Price: $4,695,000.00
  2. Price sqft: $925.12 / sqft
  3. Previous Price: $4,895,000
  4. Last Price Change: 09/10/25
  5. Days On Market: 90
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5075
  10. Acreage: 0.37 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Canal - Saltwater
  16. Year Built: 2016
MLS#: A4656098
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: MICHAEL SAUNDERS & COMPANY
  9. mfrmls
  10. DMCA Notice
LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage
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5569 Cape Leyte Drive
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Details for 5569 Cape Leyte Drive, Sarasota, FL 34242
Single Family
  1. Price: $4,695,000.00
  2. Price sqft: $925.12 / sqft
  3. Previous Price: $4,895,000
  4. Last Price Change: 08/04/25
  5. Days On Market: 90
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 5075
  10. Acreage: 0.37 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: CanalAccess,GulfAccess
  15. Year Built: 2016
MLS#: A4656098
  1. County: SARASOTA
  2. City: Sarasota
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: MICHAEL SAUNDERS & COMPANY
  9. Provided through
  10. DMCA Notice
LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage
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951 Contento St.
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Details for 951 Contento St., SIESTA KEY, FL 34242
Single Family
  1. Price: $2,299,000.00
  2. Price sqft: $645.06 / sqft
  3. Days On Market: 222
  4. Bedrooms: 3
  5. Baths: 4
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3564
  8. Acreage: 0.27 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Brackish,Canal Front
  14. Year Built: 1967
MLS#: A4639209
  1. County: SARASOTA
  2. City: SIESTA KEY
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: COLDWELL BANKER SARASOTA CENT.
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Under Construction: Nestled in one of Siesta Keys best kept secrets, The Coastal Haven is tucked away in the peaceful privacy of a relaxing cul de sacaway from the hustle and bustle, offering you an u
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5560 Shadow Lawn Drive
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Details for 5560 Shadow Lawn Drive, SARASOTA, FL 34242
Single Family
  1. Price: $1,695,000.00
  2. Price sqft: $559.41 / sqft
  3. Days On Market: 237
  4. Bedrooms: 4
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3030
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Saltwater
  13. Year Built: 1970
MLS#: A4636955
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
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  10. DMCA Notice
New price! Discover the epitome of coastal living with this stunning waterfront home on Siesta Key, steps from the world famous white sands of Siesta Beach and the aqua waters of the Gulf of Mexico. O
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1038 Contento Street
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Details for 1038 Contento Street, SARASOTA, FL 34242
Single Family
  1. Price: $1,625,000.00
  2. Price sqft: $542.75 / sqft
  3. Previous Price: $1,725,000
  4. Last Price Change: 09/03/25
  5. Days On Market: 134
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2994
  10. Acreage: 0.31 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Saltwater,Canal Front,Intracoastal Waterway
  15. Year Built: 1972
MLS#: A4650938
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: SARASELLSSARASOTA.COM
  9. mfrmls
  10. DMCA Notice
Siesta Key Canal Front Home with 175 of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world famous Siesta Key Beach rated
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5215 Cape Leyte Drive
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Details for 5215 Cape Leyte Drive, SARASOTA, FL 34242
Single Family
  1. Price: $1,625,000.00
  2. Price sqft: $593.28 / sqft
  3. Days On Market: 25
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2739
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: Canal - Saltwater
  13. Year Built: 1962
MLS#: A4662406
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: MANGROVE REALTY ASSOCIATES
  9. mfrmls
  10. DMCA Notice
SIESTA ISLES Waterfront Gem! Nestled in the back of the neighborhood, experience the best of Siesta Key living in this beautifully maintained 3 bedroom + den, 3 bath pool home with 135+ feet of fronta
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5215 Cape Leyte Drive
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Details for 5215 Cape Leyte Drive, Sarasota, FL 34242
Single Family
  1. Price: $1,625,000.00
  2. Price sqft: $593.28 / sqft
  3. Days On Market: 25
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2739
  8. Acreage: 0.35 acres
  9. Pool: Yes
  10. Waterfront: Yes
  11. Wateraccess: Yes
  12. Waterfront Type: CanalAccess
  13. Year Built: 1962
MLS#: A4662406
  1. County: SARASOTA
  2. City: Sarasota
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: MANGROVE REALTY ASSOCIATES
  9. Provided through
  10. DMCA Notice
SIESTA ISLES Waterfront Gem! Nestled in the back of the neighborhood, experience the best of Siesta Key living in this beautifully maintained 3 bedroom + den, 3 bath pool home with 135+ feet of fronta
Listing Details and 65 Additional Pictures
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5502 Shadow Lawn Drive
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Details for 5502 Shadow Lawn Drive, SARASOTA, FL 34242
Single Family
  1. Price: $1,389,000.00
  2. Price sqft: $308.39 / sqft
  3. Previous Price: $1,399,000
  4. Last Price Change: 06/10/25
  5. Days On Market: 147
  6. Bedrooms: 3
  7. Baths: 4
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 4504
  10. Acreage: 0.33 acres
  11. Pool: No
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal Front
  15. Year Built: 1961
MLS#: A4649470
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: PREFERRED SHORE LLC
  9. mfrmls
  10. DMCA Notice
Build your Dream Home or renovate the existing home on this Siesta Isles Canal Front lot just a short walk to the cool powdery quartz sands of Siesta Key. This 14,200 square foot lot boasts approximat
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5432 Cape Leyte Drive
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Details for 5432 Cape Leyte Drive, SARASOTA, FL 34242
Single Family
  1. Price: $1,295,000.00
  2. Price sqft: $595.68 / sqft
  3. Days On Market: 147
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2174
  8. Acreage: 0.34 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1974
MLS#: A4649500
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: PREMIER SOTHEBYS INTL REALTY
  9. mfrmls
  10. DMCA Notice
Grab your sunglasses and flip flops, because this charming Siesta Key retreat is just minutes from world famous Siesta Beach, the #1 beach in the USA! With powdery white sands and crystal clear, turqu
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5223 Shadow Lawn Drive
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Details for 5223 Shadow Lawn Drive, SARASOTA, FL 34242
Single Family
  1. Price: $875,000.00
  2. Price sqft: $599.73 / sqft
  3. Previous Price: $995,000
  4. Last Price Change: 06/26/25
  5. Days On Market: 114
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 1
  9. Bldg sqft: 1459
  10. Acreage: 0.35 acres
  11. Pool: Yes
  12. Waterfront: No
  13. Year Built: 1967
MLS#: A4653522
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Brookside
  7. High School: Sarasota
  8. Provided by: REAL BROKER, LLC
  9. mfrmls
  10. DMCA Notice
One or more photo(s) has been virtually staged. Elegant Siesta Key Retreat Now Offered at $875,000 Discover an unbeatable opportunity at 5223 Shadow Lawn Dr a stylish 3 bedroom, 2 bath Siesta Isl
Listing Details and 81 Additional Pictures
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