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  1. Subdivision Like Siesta Isles
5624 Cape Leyte Drive
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Details for 5624 Cape Leyte Drive, SARASOTA, FL 34242
Single Family
  1. Price: $2,249,000.00
  2. Price sqft: $719.45 / sqft
  3. Days On Market: 67
  4. Bedrooms: 5
  5. Baths: 5
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3126
  8. Acreage: 0.25 acres
  9. Pool: Yes
  10. Waterfront: No
  11. Year Built: 1963
MLS#: A4670620
  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: SARASOTA INTERNATIONAL REALTY
  9. mfrmls
  10. DMCA Notice
Discover this newly upgraded coastal retreat ideally located just behind the iconic Siesta Key Beach, where crystal clear waters and powder soft sands are only a short walk away. View of the beach mai
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5569 Contento Drive
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Details for 5569 Contento Drive, SARASOTA, FL 34242
Single Family
  1. Price: $2,099,000.00
  2. Price sqft: $780.88 / sqft
  3. Previous Price: $2,199,000
  4. Last Price Change: 12/04/25
  5. Days On Market: 71
  6. Bedrooms: 2
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2688
  10. Acreage: 0.28 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Canal - Saltwater
  16. Year Built: 1969
MLS#: A4670108
  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: RE/MAX ALLIANCE GROUP
  9. mfrmls
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New price ~ siesta key ~ siesta isles neighborhood ~ 123' water frontage ~ close to siesta key beach ~ home updated throughout (inside outside) ~ oversized lot: 12,000+ square feet ~ pool ~ two boat
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5348 Shadow Lawn Drive
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Details for 5348 Shadow Lawn Drive, SARASOTA, FL 34242
Single Family
  1. Price: $1,795,000.00
  2. Price sqft: $569.84 / sqft
  3. Days On Market: 5
  4. Bedrooms: 3
  5. Baths: 3
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 3150
  8. Acreage: 0.33 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Saltwater
  14. Year Built: 1964
MLS#: A4676391
  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 SOTHEBY'S INTERNATIONAL REALTY
  9. mfrmls
  10. DMCA Notice
Set along the Grand Canal in Siesta Isles, this inviting waterfront pool home offers an effortless blend of space, comfort and classic island living. Thoughtfully designed on a single level, the appro
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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: $1,549,000.00
  2. Price sqft: $511.22 / sqft
  3. Previous Price: $1,695,000
  4. Last Price Change: 12/02/25
  5. Days On Market: 350
  6. Bedrooms: 4
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3030
  10. Acreage: 0.33 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Saltwater
  15. 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
  9. mfrmls
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New Price Siesta Key Waterfront Living at Its Best. Discover the essence of coastal living in this beautifully appointed waterfront home on Siesta Key, just moments from the world renowned white sand
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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: $1,295,000.00
  2. Price sqft: $287.52 / sqft
  3. Previous Price: $1,389,000
  4. Last Price Change: 09/27/25
  5. Days On Market: 260
  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
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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: $1,199,000.00
  2. Price sqft: $551.52 / sqft
  3. Previous Price: $1,295,000
  4. Last Price Change: 10/01/25
  5. Days On Market: 259
  6. Bedrooms: 3
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2174
  10. Acreage: 0.34 acres
  11. Pool: No
  12. Waterfront: No
  13. 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
New Price! 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 c
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5519 Azure Way
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Details for 5519 Azure Way, SARASOTA, FL 34242
Rental
  1. Price: $12,000.00
  2. Price sqft: $3.13 / sqft
  3. Bedrooms: 4
  4. Baths: 3
  5. Garage / Parking Spaces: 1
  6. Bldg sqft: 3833
  7. Acreage: 0.37 acres
  8. Pool: Yes
  9. Spa/HotTub: Yes
  10. Waterfront: No
  11. Year Built: 1968
MLS#: A3984202
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Provided by: JENNETTE PROPERTIES, INC.
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Sprawling 4 bed. plus Waterfront/Pool/Spa home is only 4 min. to World famous Siesta Key Beach!!!Tucked away on the little "island "of Azure Way you are afforded privacy with water views . Perfect for
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5640 Cape Leyte Drive
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Details for 5640 Cape Leyte Drive, SARASOTA, FL 34242
Rental
  1. Price: $8,000.00
  2. Price sqft: $2.93 / sqft
  3. Days On Market: 631
  4. Bedrooms: 3
  5. Baths: 2
  6. Bldg sqft: 2729
  7. Acreage: 0.26 acres
  8. Pool: Yes
  9. Waterfront: No
  10. Year Built: 1964
MLS#: A4607612
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Provided by: ASCENDIA REAL ESTATE
  6. mfrmls
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It's all about the beach and the bourbon! This 1964 Siesta Key classic beach house with terrazzo flooring has been totally updated! So you and your family or friends can enjoy the 3 bedroom and 2 bath
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5577 Contento Drive
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Details for 5577 Contento Drive, SARASOTA, FL 34242
Rental
  1. Price: $5,000.00
  2. Price sqft: $2.39 / sqft
  3. Days On Market: 632
  4. Bedrooms: 2
  5. Baths: 2
  6. Bldg sqft: 2089
  7. Acreage: 0.26 acres
  8. Pool: Yes
  9. Waterfront: Yes
  10. Wateraccess: Yes
  11. Waterfront Type: Canal - Saltwater
  12. Year Built: 1969
MLS#: A4607468
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Provided by: ASCENDIA REAL ESTATE
  6. mfrmls
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This is a short term rental. Listing reflects off season rate. Available peak season month: January 3rd 31st, 2026. Welcome to Bikini Tini Time! Your completely remodeled Siesta Key paradise awaits
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Tropic Shores Realty - Crystal River
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Listings provided courtesy of The Hernando County Association of Realtors MLS.
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Datafeed Last updated on January 8, 2026 @ 12:00 am
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