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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: $4,950,000.00
  2. Price sqft: $772.83 / sqft
  3. Previous Price: $5,395,000
  4. Last Price Change: 04/11/26
  5. Days On Market: 165
  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
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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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5569 Cape Leyte Drive
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Details for 5569 Cape Leyte Drive, SARASOTA, FL 34242
Single Family
  1. Price: $4,495,000.00
  2. Price sqft: $885.71 / sqft
  3. Days On Market: 37
  4. Bedrooms: 5
  5. Baths: 4
  6. Garage / Parking Spaces: 3
  7. Bldg sqft: 5075
  8. Acreage: 0.37 acres
  9. Pool: Yes
  10. Spa/HotTub: Yes
  11. Waterfront: Yes
  12. Wateraccess: Yes
  13. Waterfront Type: Canal - Saltwater
  14. Year Built: 2016
MLS#: A4685577
  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
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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 front
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951 Contento St.
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Details for 951 Contento St., SIESTA KEY, FL 34242
Single Family
  1. Price: $2,000,000.00
  2. Price sqft: $561.17 / sqft
  3. Days On Market: 38
  4. Bedrooms: 3
  5. Baths: 3
  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 - Saltwater
  14. Year Built: 1967
MLS#: A4684955
  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: PREMIER SOTHEBY'S INTERNATIONAL REALTY
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Deep boating water on the Grand Canal and Siesta Keys world famous beaches just minutes away, experience the best of island living. This beautifully renovated three bedroom, three bath waterfront resi
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814 Paradise Way
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Details for 814 Paradise Way, SARASOTA, FL 34242
Single Family
  1. Price: $1,995,000.00
  2. Price sqft: $632.13 / sqft
  3. Previous Price: $2,100,000
  4. Last Price Change: 03/30/26
  5. Days On Market: 43
  6. Bedrooms: 4
  7. Baths: 2
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 3156
  10. Acreage: 0.31 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Saltwater
  15. Year Built: 1962
MLS#: TB8483961
  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: COMMUNITY REALTY ASSOCIATES
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Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn key, move in ready 4 bedrooms and 2 bathrooms home in one of the islands most desirable and tranquil locations. Si
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5507 Contento Drive
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Details for 5507 Contento Drive, SARASOTA, FL 34242
Single Family
  1. Price: $1,775,000.00
  2. Price sqft: $604.98 / sqft
  3. Previous Price: $1,795,000
  4. Last Price Change: 03/07/26
  5. Days On Market: 57
  6. Bedrooms: 3
  7. Baths: 3
  8. Garage / Parking Spaces: 2
  9. Bldg sqft: 2934
  10. Acreage: 0.32 acres
  11. Pool: Yes
  12. Waterfront: Yes
  13. Wateraccess: Yes
  14. Waterfront Type: Canal - Saltwater
  15. Year Built: 1969
MLS#: A4683288
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Elementary School: Phillippi Shores
  6. Middle School: Sarasota
  7. High School: Sarasota
  8. Provided by: PREFERRED SHORE LLC
  9. mfrmls
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A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying
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5448 Azure Way
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Details for 5448 Azure Way, SARASOTA, FL 34242
Land
  1. Price: $1,750,000.00
  2. Days On Market: 18
  3. Acreage: 0.33 acres
  4. Pool: No
  5. Waterfront: Yes
  6. Wateraccess: Yes
  7. Waterfront Type: Canal - Saltwater
  8. Year Built: Not Available
MLS#: A4688348
  1. County: SARASOTA
  2. City: SARASOTA
  3. Zipcode: 34242
  4. Subdivision: Siesta Isles
  5. Provided by: PREMIER SOTHEBY'S INTERNATIONAL REALTY
  6. mfrmls
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Discover an exceptional waterfront homesite in the heart of Siesta Key, one of Floridas sought after coastal destinations. On a quiet, no through traffic cul de sac in the exclusive Siesta Isles encla
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742 Edgemere
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Details for 742 Edgemere, SIESTA KEY, FL 34242
Single Family
  1. Price: $1,750,000.00
  2. Price sqft: $1,203.58 / sqft
  3. Days On Market: 41
  4. Bedrooms: 3
  5. Baths: 2
  6. Garage / Parking Spaces: 2
  7. Bldg sqft: 1454
  8. Acreage: 0.37 acres
  9. Pool: No
  10. Waterfront: No
  11. Year Built: 1964
MLS#: W7883717
  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: LISTWITHFREEDOM.COM
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Build or Renovate Discover an exceptional waterfront opportunity in the coveted Siesta Isles neighborhood on Siesta Key. Situated on an oversized lot at the intersection of two canals, this propert
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5569 Contento Drive
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Details for 5569 Contento Drive, SARASOTA, FL 34242
Single Family
  1. Price: $1,749,000.00
  2. Price sqft: $650.67 / sqft
  3. Previous Price: $2,099,000
  4. Last Price Change: 02/20/26
  5. Days On Market: 171
  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
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Siesta key ~ updated pricing with owner financing option ~ siesta isles neighborhood ~ 123' water frontage ~ close to siesta key beach ~ home updated throughout (inside outside) ~ oversized lot: 12,
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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: 451
  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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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: 87
  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
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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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