Siesta Isles Homes on Siesta Key, Florida

Siesta Isles offers 295 beautiful waterfront properties that are situated on two small man made islands in the center of Siesta Key just north of Siesta Key Beach. Many of these homes have swimming pools and screened-in lanais. Prior to this real estate being developed, this area of Siesta Key was very low and storm surges would not have the means to recede. Canals were constructed to allow drainage for the island and sometimes provide limited access to the Intracoastal Waterway for small watercraft.

Homes For Sale in Siesta Isles

All Listings Under $100,000 $500,000 - $600,000
$700,000 - $800,000 $800,000 - $900,000 $900,000 - $1,000,000
Over $1,000,000
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5532 Cape Aqua Dr, Sarasota $1,599,999

  • 4 Beds
  • 3.0 Baths
  • 3,377 SqFt
  • 0.36 Acres

Brand New, Ready By April, Blocks From Famous Siesta Key Beach And Village. Designed And Crafted By Respected Local Builder Rob Allegra Of Allegra Homes. Photos Are From A Complete Decorated Version Of This Home And Available To Be Seen By Appointment. This...

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813 Idlewild Way, Sarasota $1,273,000

  • 5 Beds
  • 4.0 Baths
  • 4,161 SqFt
  • 0.31 Acres

Strategically Located On The Grand Canal On World-famous Siesta Key. This Renovated, Spacious, Two-story Pool Home Is In The Premier Neighborhood Of Siesta Isles, Where Beach And Boating Are A Way Of Life. Generous Living Spaces Along With Five Bedrooms And...

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815 Paradise Way, Sarasota $1,249,900

  • 4 Beds
  • 4.0 Baths
  • 3,677 SqFt
  • 0.33 Acres

On A Quiet Cul-de-sac In The Neighborhood Of Siesta Isles Is This Lovingly Maintained Canal Front Home With Boating Access To The Grand Canal With Only One Bridge To The Intracoastal Waterways. Upon Entering Through The Double Entry Raised Panel Front Doors...

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5265 Cape Leyte Way, Siesta Key $995,000

  • 3 Beds
  • 3.0 Baths
  • 2,453 SqFt
  • 0.38 Acres

This Recently Renovated 3 Bedroom Siesta Isles Property Offers A Rare 180 Feet Of Canal Front And Is Located At The End Of Quiet Street. This Home Has Recently Received New Hurricane Sliders, 2 A/c Units, And Marble Bathroom Vanities Along With Fresh Paint ...

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940 Contento S Cir, Sarasota $949,000

  • 3 Beds
  • 2.0 Baths
  • 1,976 SqFt
  • 0.27 Acres

Move In Ready Siesta Isles Waterfront Canal Home And Just A Short Few Blocks To The Beach. This Home Has Been Brought Back To Premium Condition. The Landscaping Is Superb With The Addition Of New Brick Driveway, Walks, Sundeck, Patio And Circle Guest Driv...

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1030 Contento St, Sarasota $939,000

  • 4 Beds
  • 3.0 Baths
  • 1,884 SqFt
  • 0.38 Acres

Welcome To Paradise And One Of The Prettiest And Private Lots In Siesta Isles! Imagine Waking Up Each Morning And Having Coffee By Your Pool Overlooking The Tranquil Canal Water As The Palm Trees Sway In The Gentle Breeze. Enjoy The Convenience Of Having Y...

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5273 Cape Leyte Way, Sarasota $800,000

  • 3 Beds
  • 2.0 Baths
  • 2,101 SqFt
  • 0.38 Acres

This Vintage Sarasota School Of Architecture, Mid-century Modern Home Is Located Close To Siesta Beach On A 16,400 Sq. Ft. Lot On The Grand Canal. This Deep Boating Water Lot With A Wide Harbor View Is On A Charming Cul-de-sac. The Original Sarasota School ...

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5273 Cape Leyte Way, Sarasota $800,000

  • 0.38 Acres

This Waterfront Property Is Located On A Charming Cul-de-sac Close To Siesta Beach On Deep Boating Water Of The Grand Canal, With Wide And Long Harbor Views. The Original Home Was Designed By Architect Tim Seibert But Has Not Been Occupied In Recent Years; ...

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808 Idlewild Way, Sarasota $789,000

  • 3 Beds
  • 2.0 Baths
  • 1,843 SqFt
  • 0.31 Acres

Look No Further! You’ve Patiently Waited For The Perfect Waterfront Property To Remodel. You Found It! Ideal Location In Popular & Sought After Siesta Isles. Located On A Quiet Cul-de-sac With Preferred Southern Exposure Out Back. Nearly 1/3 Of An Acre...

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1034 Glebe Ln, Sarasota $549,000

  • 3 Beds
  • 2.0 Baths
  • 1,880 SqFt
  • 0.40 Acres

What An Amazing Property In Siesta Isles! Conveniently Located Minutes To Siesta Key Beach And Glebe Park!! This Three Bedroom Two Bath Pool Home Has So Much Potential!! French Doors Open Up To A Newly Resurfaced Pool Deck! It Sits On A 17,000+ Square F...

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5519 Azure Way, Sarasota $8,000

  • 4 Beds
  • 3.0 Baths
  • 2,460 SqFt
  • 0.37 Acres

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 Large And/or Multiple Families And Guests Who Want Toenj...

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5525 Azure Way, Sarasota $8,000

  • 5 Beds
  • 4.0 Baths
  • 3,952 SqFt
  • 0.63 Acres

Fabulous Large Home Decorated To Perfection Just Over 400 Steps From Siesta Public Beach, One The Of The Best Beaches In The World. House Is Large And Has 5 En Suite Bedrooms. Enormous Poolwith Lions Head Fountains And Hot Tub Overlooking The Wide Canal. ...

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More About Siesta Isles

Built in the 1960’s and 70’s, most of the homes on Siesta Isles are primarily Florida Ranch designs. These were very popular during that era. Prices for the homes in the community vary because of older structures being torn down to make way for newer ones. The residences located in Siesta Isles can be found on Cape Aqua Drive, Azure Way, Shadow Lawn Way, Contento Street, Cape Leyte Drive, and Idlewild Way.

The finest and whitest sand in the world is an award that Siesta Key Beach has been recognized for. At the Great International White Sand Beach Challenge held in 1987, Siesta Key Beach won the title of “whitest and finest sand in the
world”. The homes located on the southern end of Siesta Isles are within walking distance to this amazing beach. In 2011, Dr. Beach rated Siesta Key Beach #1 in the nation.

Visit our Siesta Key real estate page to view other great places to live in Sarasota, Florida. If Roberts Point fits your budget and requirements then you should also explore Bayou Louise, Cocoanut Bayou, Gulfmead Estates, Bay Island, Siesta Bayside and Roberts Point.

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS.

Listing information last updated on May 24th, 2015 at 6:00am EDT.