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    1. Subdivision Like Siesta Isles
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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: 60
    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 Elementary
    6. Middle School: Brookside Middle
    7. High School: Sarasota High
    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 front
    Listing Details and 67 Additional Pictures
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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: 65
    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 Elementary
    6. Middle School: Brookside Middle
    7. High School: Sarasota High
    8. Provided by: COMMUNITY REALTY ASSOCIATES
    9. mfrmls
    10. DMCA Notice
    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
    Listing Details and 24 Additional Pictures
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    951 Contento St.
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    Details for 951 Contento St., SIESTA KEY, FL 34242
    Single Family
    1. Price: $1,950,000.00
    2. Price sqft: $547.14 / sqft
    3. Previous Price: $2,000,000
    4. Last Price Change: 05/03/26
    5. Days On Market: 60
    6. Bedrooms: 3
    7. Baths: 3
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 3564
    10. Acreage: 0.27 acres
    11. Pool: Yes
    12. Spa/HotTub: Yes
    13. Waterfront: Yes
    14. Wateraccess: Yes
    15. Waterfront Type: Canal - Saltwater
    16. Year Built: 1967
    MLS#: A4684955
    1. County: SARASOTA
    2. City: SIESTA KEY
    3. Zipcode: 34242
    4. Subdivision: Siesta Isles
    5. Elementary School: Phillippi Shores Elementary
    6. Middle School: Brookside Middle
    7. High School: Sarasota High
    8. Provided by: PREMIER SOTHEBY'S INTERNATIONAL REALTY
    9. mfrmls
    10. DMCA Notice
    New pricing! 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 wa
    Listing Details and 52 Additional Pictures
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    18260 Deep Passage Ln
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    Details for 18260 Deep Passage Ln, FORT MYERS BEACH, FL 33931
    Single Family
    1. Price: $1,799,000.00
    2. Price sqft: $315.61 / sqft
    3. Bedrooms: 4
    4. Baths: 4
    5. Garage / Parking Spaces: 2
    6. Bldg sqft: 5700
    7. Acreage: 0.21 acres
    8. Pool: Yes
    9. Spa/HotTub: Yes
    10. Waterfront: Yes
    11. Wateraccess: Yes
    12. Waterfront Type: Canal Front, Navigable, Seawall
    13. Year Built: 1983
    MLS#: 2026016415
    1. County: LEE
    2. City: FORT MYERS BEACH
    3. Zipcode: 33931
    4. Subdivision: Siesta Isles
    5. Provided by: Premiere Plus Realty Company
    6. Provided through
    7. DMCA Notice
    Exceptional boating and exceptional value in one of the best waterfront locations in the entire region. Situated on a quiet cul de sac in desirable Siesta Isles, this 3,049 sq ft fully furnished home
    Listing Details and 44 Additional Pictures
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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: 04/30/26
    5. Days On Market: 79
    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 Elementary
    6. Middle School: Sarasota Middle
    7. High School: Sarasota High
    8. Provided by: PREFERRED SHORE LLC
    9. mfrmls
    10. DMCA Notice
    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
    Listing Details and 90 Additional Pictures
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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: 40
    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
    7. DMCA Notice
    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
    Listing Details and 44 Additional Pictures
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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: 02/21/26
    5. Days On Market: 194
    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 Elementary
    6. Middle School: Brookside Middle
    7. High School: Sarasota High
    8. Provided by: RE/MAX ALLIANCE GROUP
    9. mfrmls
    10. DMCA Notice
    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,
    Listing Details and 78 Additional Pictures
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    742 Edgemere
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    Details for 742 Edgemere, SIESTA KEY, FL 34242
    Single Family
    1. Price: $1,700,000.00
    2. Price sqft: $1,169.19 / sqft
    3. Previous Price: $1,750,000
    4. Last Price Change: 04/26/26
    5. Days On Market: 63
    6. Bedrooms: 3
    7. Baths: 2
    8. Garage / Parking Spaces: 2
    9. Bldg sqft: 1454
    10. Acreage: 0.37 acres
    11. Pool: No
    12. Waterfront: No
    13. Year Built: 1964
    MLS#: W7883717
    1. County: SARASOTA
    2. City: SIESTA KEY
    3. Zipcode: 34242
    4. Subdivision: Siesta Isles
    5. Elementary School: Phillippi Shores Elementary
    6. Middle School: Brookside Middle
    7. High School: Sarasota High
    8. Provided by: LISTWITHFREEDOM.COM
    9. mfrmls
    10. DMCA Notice
    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
    Listing Details and 35 Additional Pictures
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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: $1,499,000.00
    2. Price sqft: $494.72 / sqft
    3. Days On Market: 473
    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 Elementary
    6. Middle School: Brookside Middle
    7. High School: Sarasota High
    8. Provided by: PREMIER SOTHEBYS INTL REALTY
    9. mfrmls
    10. DMCA Notice
    Newly Priced Siesta Key Waterfront Blocks to the beach! An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this well maintained residence is ideally positioned just minutes fr
    Listing Details and 46 Additional Pictures
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    18323 Cutlass Dr
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    Details for 18323 Cutlass Dr, FORT MYERS BEACH, FL 33931
    Single Family
    1. Price: $1,488,000.00
    2. Price sqft: $433.06 / sqft
    3. Bedrooms: 2
    4. Baths: 2
    5. Garage / Parking Spaces: 2
    6. Bldg sqft: 3436
    7. Acreage: 0.23 acres
    8. Pool: Yes
    9. Waterfront: Yes
    10. Wateraccess: Yes
    11. Waterfront Type: Canal Front, Seawall
    12. Year Built: 1975
    MLS#: 2026018870
    1. County: LEE
    2. City: FORT MYERS BEACH
    3. Zipcode: 33931
    4. Subdivision: Siesta Isles
    5. Provided by: Michael Saunders & Company
    6. Provided through
    7. DMCA Notice
    Stepping into this home, youre immediately welcomed by a bright, open living space designed for both comfort and entertainment. The expansive great room flows seamlessly into the chefs kitchen, with e
    Listing Details and 41 Additional Pictures
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    Equal Housing Opportunity
    Listings provided courtesy of The Hernando County Association of Realtors MLS.
    Listing Data ©2026 REALTOR® Association of Citrus County
    The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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    Datafeed Last updated on May 11, 2026 @ 12:00 am
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