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 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $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 $1,298,000

  • 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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5265 Cape Leyte Way, Siesta Key $1,025,000

  • 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 $979,000

  • 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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918 Contento St, Sarasota $899,000

  • 3 Beds
  • 3.0 Baths
  • 2,390 SqFt
  • 0.28 Acres

This Island Style Living Home Sits On An Over-sized Lot Nestled On A Quiet Cul-de-sac With 140' Of Seawall On The Grand Canal And One Bridge To The Inter-coastal Waterway And Sarasota Bay. This Beautiful Landscaped Light And Bright Home Offers A Comfortabl...

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5456 Azure Way, Sarasota $889,000

  • 3 Beds
  • 3.0 Baths
  • 2,476 SqFt
  • 0.34 Acres

Premium Siesta Key Canalfront Location * Bring Your Boat! * Sparkling Heated Pool & Spa * Short Walk To World Renowned Siesta Beach * Prime Location In This Open & Airy 1-story Siesta Isles Home * 3 Bedroom, 3 Full Bath In This Split Floor Plan * Large Gall...

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5273 Cape Leyte Way, Sarasota $800,000

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

This Is A Grand Canal Waterfront Oversized Lot On A Charming Cul-de-sac And Wide Waterway. Great Potential. The Home Situated On The Property Is An Original Sarasota School Of Architecture Home Designed By Tim Seibert But Has Not Been Occupied In Years And ...

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5273 Cape Leyte Way, Sarasota $800,000

  • 0.38 Acres

This Is A Grand Canal Waterfront Oversized Lot On A Charming Cul-de-sac And Wide Waterway. Great Potential. The Home Situated On The Property Is An Original Sarasota School Of Architecture Home Designed By Tim Seibert But Has Not Been Occupied In Years And ...

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5560 Contento Dr, Sarasota $659,000

  • 3 Beds
  • 2.0 Baths
  • 1,679 SqFt
  • 0.26 Acres

The Perfect Lifestyle- A Siesta Key Waterfront Home Near The Beach With A Deep Water Dock And Boat Lift On The Grand Canal. Just .5 Mile To The Powdery White Sands Of Siesta Beach, One Of Usa’s Top Beaches. This Three Bedroom, Two Bath Split-plan Home Offer...

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5432 Cape Leyte Dr, Sarasota $619,000

  • 2 Beds
  • 2.0 Baths
  • 1,659 SqFt
  • 0.34 Acres

Siesta Key - Location~location! This Pristine, Well Kept Home Is Situated On A Oversized Private Lot With A Circular Drive On A Quite Street. The Large Glass Windows In Back Provide A Tropical Paradise View. The Kitchen Is An Open Plan With Stainless Appli...

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1034 Glebe Ln, Sarasota $599,000

  • 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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5229 Shadow Lawn, Sarasota $465,000

  • 3 Beds
  • 2.0 Baths
  • 1,582 SqFt
  • 0.35 Acres

Short Sale. Price Just Reduced. Live The Island Lifestyle! Quiet And Peaceful 3 Bedroom 2 Bath Home In Lovely Siesta Isles Near World Famous Siesta Key Beach. Enjoy The Easy Care Natural Florida Landscaping On Extra Large Lot. Love The Sparkling Pool With S...

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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 March 3rd, 2015 at 9:04pm EST.