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  1. Subdivision Like Siesta Isles
  2. Listing Status = Active
5362 Shadow Lawn Drive
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Details for 5362 Shadow Lawn Drive, SARASOTA, FL 34242
Single Family
  1. Price: $5,495,000.00
  2. Price sqft: $857.92 / sqft
  3. Previous Price: $5,649,000
  4. Last Price Change: 12/18/25
  5. Days On Market: 103
  6. Bedrooms: 3
  7. Baths: 5
  8. Garage / Parking Spaces: 3
  9. Bldg sqft: 6405
  10. Acreage: 0.32 acres
  11. Pool: Yes
  12. Spa/HotTub: Yes
  13. Waterfront: Yes
  14. Wateraccess: Yes
  15. Waterfront Type: Canal - Saltwater
  16. Year Built: 2023
MLS#: A4667008
  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: NCC PROPERTIES LLC
  9. mfrmls
  10. DMCA Notice
Experience elevated coastal living in this award winning Marlin Model by Nutter Custom Construction, perfectly positioned on Siesta Keys coveted Grand Canal. Completed in 2023 and showcased as the bui
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5624 Cape Leyte Drive
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Details for 5624 Cape Leyte Drive, SARASOTA, FL 34242
Single Family
  1. Price: $2,199,000.00
  2. Price sqft: $703.46 / sqft
  3. Previous Price: $2,249,000
  4. Last Price Change: 01/21/26
  5. Days On Market: 105
  6. Bedrooms: 5
  7. Baths: 5
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3126
  10. Acreage: 0.25 acres
  11. Pool: Yes
  12. Waterfront: No
  13. 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: 109
  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
  10. DMCA Notice
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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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: 388
  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
  10. DMCA Notice
Siesta Key Waterfront LivingPriced to Embrace the Island Lifestyle An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this beautifully maintained residence is ideally positio
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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: $1,150,000.00
  2. Price sqft: $528.98 / sqft
  3. Previous Price: $1,199,000
  4. Last Price Change: 02/07/26
  5. Days On Market: 298
  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
Exceptional Opportunity on Siesta Key. Now offered at a newly adjusted price, this charming Siesta Key retreat presents an outstanding opportunity to own just minutes from world famous Siesta Beachcon
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1002 Glebe Lane
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Details for 1002 Glebe Lane, SARASOTA, FL 34242
Single Family
  1. Price: $1,150,000.00
  2. Price sqft: $480.37 / sqft
  3. Days On Market: 15
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 2394
  8. Acreage: 0.23 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: No
  12. Year Built: 1967
MLS#: A4679533
  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
Beautifully remodeled and ideally just minutes from world renowned white sands of Siesta Beach, this chic island pool home offers an exceptional blend of style, comfort and storm ready peace of mind.
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734 Canal Road
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Details for 734 Canal Road, SARASOTA, FL 34242
Single Family
  1. Price: $995,000.00
  2. Price sqft: $571.51 / sqft
  3. Days On Market: 25
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 1
  7. Bldg sqft: 1741
  8. Acreage: 0.28 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1963
MLS#: A4675607
  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
Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity awaits. A prime 12,229 square foot property in sough
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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.
  6. mfrmls
  7. DMCA Notice
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: 669
  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
  7. DMCA Notice
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: 670
  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
  7. DMCA Notice
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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