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 $900,000 - $1,000,000
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5532 Cape Aqua Dr, Sarasota $1,549,000

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

Brand New, 2015 Award Winning Model Design, 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 ...

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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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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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5409 Azure Way, Sarasota $699,000

  • 3 Beds
  • 2.0 Baths
  • 1,972 SqFt
  • 0.32 Acres

This Is A Perfect Location At The End Of The Cul-de-sac And With An Exceptional Wide View Of The Grand Canal On Siesta Key. The Views Are Spectacular From The 112 Foot Canal Lot. Be Sure To Check Out The Video Under The "virtual Tour" Link! Demand For Si...

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5229 Shadow Lawn Dr, Sarasota $509,900

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

Make Your Dream Of Owning A Home On Siesta Key A Reality. This Lovely 3 Bedroom 2 Bath Pool Home Is Tropical Living At Its Finest. The Florida Tropical Landscaping Requires Minimal Upkeep And More Time For You To Enjoy The Beach. The Floor Plan Offers A For...

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5333 Shadow Lawn Dr, Sarasota $435,000

  • 3 Beds
  • 2.0 Baths
  • 1,594 SqFt
  • 0.38 Acres

Opportunity Knocks On Siesta Key. Sought After Siesta Isles Location. This Home Is Waiting For Your Remodeling Touches. Nice Flow To The Home With Large Kitchen Open To The Great Room.2 Baths Currently Plus A Third Is Plumbed. All 3 Bedrooms Have Terrazzo 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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5613 Cape Leyte Dr, Sarasota $6,000

  • 3 Beds
  • 2.0 Baths
  • 2,332 SqFt

This Gorgeous Mediterranean-style Home Has Great Curb Appeal And Is Situated On Deep Boating Grand Canal. Large Screened Lanai, Solar-heated Pool, Florida Room With Office Space And Pullout Twin Sleepers. Master Has 2 Over-sized Closets And Over-sized Bath...

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742 Edgemere Ln, Sarasota $4,800

  • 3 Beds
  • 2.0 Baths
  • 1,454 SqFt
  • 0.37 Acres

Seasonal Short Term Turnkey Furnished Canal Home. Your Home Away From Home ---a Beautiful 3 Bedroom House Is Located In A Quiet, Upscale Neighborhood Not Far From Siesta Beach, The Largest And Most Beautiful Beach On The Key. Also Near Siesta Village For ...

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5640 Cape Leyte Dr, Sarasota $4,500

  • 3 Beds
  • 2.0 Baths
  • 1,628 SqFt

Bring The Family And Enjoy The Powdery White Sand And Gorgeous Sunsets Of World Famous Siesta Key Beach, Voted #1 On The Top 10 List Of America's Best Beaches 2011 By Dr. Beach And Located Less Than 2 Blocks From This Perfect Winter Getaway. This Freshlyde...

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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.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on July 4th, 2015 at 7:27pm EDT.