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 2:26 AM
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 1-10 of 17
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... 

More Details

$5,000
Provided courtesy of ASCENDIA REAL ESTATE
18 Photos 5518 Shadow Lawn Drive Sarasota, FL 34242

5518 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Rental

MLS# A4658266 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1790 Sqft
Type: SingleFamilyResidence, Area: 34242 - Sarasota/crescent Beach/siesta Key

2 Bedroom, 2 Bath home on Siesta Key with deep water canal access. Bring your boat & kayaks! Concrete seawall with dock. Home has been completely r... 

More Details

$5,500
Provided courtesy of RE/MAX ALLIANCE GROUP
21 Photos 935 Contento St Sarasota, FL 34242

935 Contento St
Sarasota, FL 34242
Siesta Isles
Rental

MLS# A4653695 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2098 Sqft
Type: SingleFamilyResidence, Area: 34242 - Sarasota/crescent Beach/siesta Key

Rare waterfront Siesta Key pool home available for annual rental! This beautifully-renovated 3/2/2 pool home in Siesta Isles is available for immed... 

More Details

$5,995
Provided courtesy of MOUNT VERNON PROPERTY MGMT INC
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... 

More Details

$8,000
Provided courtesy of ASCENDIA REAL ESTATE
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... 

More Details

$749,900
Reduced -$45,100
Provided courtesy of ACCARDI & ASSOCIATES REAL ESTA
9 Photos 5587 Shadow Lawn Drive Sarasota, FL 34242

5587 Shadow Lawn Drive
Sarasota, FL 34242
Siesta Isles
Vacant Land

MLS# A4657583 / Active

Nestled on picturesque Shadow Lawn Drive, this 12,800-square-foot lot offers an exceptional canvas for your custom home. Framed by mature live oaks... 

More Details

$850,000
Provided courtesy of COLDWELL BANKER REALTY
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... 

More Details

$875,000
Reduced -$120,000
Provided courtesy of REAL BROKER, LLC
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... 

More Details

$994,000
Reduced -$31,000
Provided courtesy of IRONGATE REALTY INC
33 Photos 734 Canal Road Sarasota, FL 34242

734 Canal Road
Sarasota, FL 34242
Siesta Isles
Vacant Land

MLS# A4650975 / Active

Endless possibilities just two blocks from Siesta Beach! Whether you're looking to build a new island retreat or remodel the existing structure, op... 

More Details

$1,000,000
Provided courtesy of PREMIER SOTHEBYS INTL REALTY
52 Photos 734 Canal Road Sarasota, FL 34242

734 Canal Road
Sarasota, FL 34242
Siesta Isles
Residential

MLS# A4651051 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1412 Sqft
Area: 34242 - Sarasota/crescent Beach/siesta Key, Subdivision: Siesta Isles

Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity... 

More Details

$1,000,000
Provided courtesy of PREMIER SOTHEBYS INTL REALTY

Broker Reciprocity The information being provided by © 2025 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 07-27-2025 2:01 AM EST.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions