David Shippey
863.521.4517

siesta isles Real Estate

Market Snapshot of Listings in siesta isles - Sarasota, FL 34242
The current prices for all Real Estate Listings in siesta isles - Sarasota, FL are reflected in the the table below.
Averages based on current search criteria as of 07/27/2025 3:58 PM
Class Total Number Price Beds Baths Age
Vacant Land2$925,000---
Rental4$6,1242.5258.8
Residential11$1,683,7893.12.755.6
Displaying results 11-17 of 17
97 Photos 1038 Contento Street Sarasota, FL 34242

1038 Contento Street
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4650938 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2217 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

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... 

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$1,725,000
Provided courtesy of SARASELLSSARASOTA.COM
41 Photos 5577 Contento Drive Sarasota, FL 34242

5577 Contento Drive
Sarasota, FL 34242
Siesta Isles
Rental

MLS# A4607468 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1424 Sqft
Type: SingleFamilyResidence, Area: 34242 - Sarasota/crescent Beach/siesta Key

Check out this COMPLETELY REMODELED canal-front pool home on Siesta Key! Picture this: you roll out of bed and grab your coffee, take two steps out... 

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$5,000
Provided courtesy of ASCENDIA REAL ESTATE
58 Photos 5640 Cape Leyte Drive Sarasota, FL 34242

5640 Cape Leyte Drive
Sarasota, FL 34242
Siesta Isles
Rental

MLS# A4607612 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2002 Sqft
Type: SingleFamilyResidence, Area: 34242 - Sarasota/crescent Beach/siesta Key

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... 

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$8,000
Provided courtesy of ASCENDIA REAL ESTATE
82 Photos 5223 Shadow Lawn Drive Sarasota, FL 34242

5223 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4653522 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1459 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

One or more photo(s) has been virtually staged. Elegant Siesta Key Retreat - Now Offered at $875,000Discover an unbeatable opportunity at 5223 Shad... 

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$875,000
Reduced -$120,000
Provided courtesy of REAL BROKER, LLC
26 Photos 5369 Shadow Lawn Drive Sarasota, FL 34242

5369 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# N6139320 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1348 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Discover a rare opportunity to own a piece of Siesta Key history with this early Ruth Richmond designed single family home, ideally situated on a s... 

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$749,900
Reduced -$45,100
Provided courtesy of ACCARDI & ASSOCIATES REAL ESTA
66 Photos 5353 Shadow Lawn Drive Sarasota, FL 34242

5353 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4654465 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1596 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

With NO WATER DAMAGE OR WATER INTRUSION, you can have peace of mind that you are getting a MOVE IN READY piece of tranquility on the beautiful, wor... 

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$994,000
Reduced -$31,000
Provided courtesy of IRONGATE REALTY INC
81 Photos 5581 Shadow Lawn Drive Sarasota, FL 34242

5581 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4653589 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2120 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Your Siesta Key dream starts right here! This spectacular, fully renovated 4-bedroom, 3-bath home in the highly sought-after Siesta Isles community... 

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$1,695,000
Provided courtesy of MICHAEL SAUNDERS & COMPANY

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