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 $600,000 - $700,000
$700,000 - $800,000 $900,000 - $1,000,000 Over $1,000,000
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840 Edgemere Ln, Sarasota $1,375,000

  • 4 Beds
  • 3.0 Baths
  • 2,796 SqFt
  • 0.17 Acres

A Peaceful Drive Along A Canopy Road Leads To This Remarkable Waterfront Coastal Contemporary On The Grand Canal At Siesta Key. A Complete Re-design And Renovation From 2012-2015 Transformed This Former Artist’s Haven Into An Exemplary Example Of Thoughtful...

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5464 Azure Way, Sarasota $1,349,000

  • 3 Beds
  • 3.0 Baths
  • 2,057 SqFt
  • 0.34 Acres

Welcome To A Truly Unique Opportunity To Walk Into A Completely Remodeled, Turn Key Furnished Coastal Contemporary Beach & Boat Lifestyle Home. Positioned Only 0.3 Miles To Siesta Public Beach & 1.1 Miles To Siesta Village, Yet It's Tucked Away On A Quiet C...

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1046 Contento St, Sarasota $1,150,000

  • 4 Beds
  • 3.0 Baths
  • 2,857 SqFt
  • 0.25 Acres

This Siesta Key Waterfront Home Is For Boaters And Beach Lovers Alike. With Over 2,850 Square Feet Of Living Area, This Updated Three Or Four Bedroom, Two-and-a-half-bath Island Home Offers A Large, Open-concept, Split-bedroom Floor Plan With Hardwood Floor...

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5232 Shadow Lawn Dr, Sarasota $988,000

  • 3 Beds
  • 3.0 Baths
  • 1,977 SqFt
  • 0.32 Acres

Siesta Key 3 Bedroom, 3 Bath, 2 Car Garage, Heated Salt Water Pool And Spectacular Long Canal Views With Private Boat Dock And Boat Slip. Oversized Lanai With Outdoor Kitchen, Makes Outdoor Living A Total Pleasure. Outside Kitchen Has Refrigerator, Ice Ma...

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924 Contento Cir, Sarasota $920,000

  • 4 Beds
  • 3.0 Baths
  • 1,834 SqFt
  • 0.26 Acres

Beautiful Siesta Isles Home Lovingly Maintained By Same Owners For 30 Years. Breathtaking Waterfront With Boat Lifts And Dock. Newer Roof, Newer Refrigerator, Windows Replaced In 2000, Newer Water Treatment System. Relax On The Beautiful Lanai With Its Gorg...

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5217 Shadow Lawn Dr, Sarasota $749,000

  • 4 Beds
  • 2.0 Baths
  • 2,421 SqFt
  • 0.35 Acres

Experience The Island Lifestyle At This 4 Bedroomed, 2 Bathroom, Pool Home On Siesta Key. Nestled On A Large Oversized Private Lot In The Much Sought After Neighborhood Of Siesta Isles, Your Own Private Paradise Awaits. With Over 2,400sqft Of Living Space...

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5534 Cape Leyte Dr, Sarasota $749,000

  • 3 Beds
  • 3.0 Baths
  • 2,157 SqFt
  • 0.34 Acres

Fabulous Location! Closest Home To The Beach In The Quaint Siesta Isles Neighborhood Listed At Under 1 Million Dollars! Lovely Spot With Private Pool & Yard Only Steps To The Beach! This Easy Living, Free Flowing, Split 3 Bedroom, 3 Full Bath, Open Floor...

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5327 Shadow Lawn Dr, Sarasota $699,000

  • 4 Beds
  • 3.0 Baths
  • 2,252 SqFt
  • 0.35 Acres

Charming 4 Bedroom 3 Bath Pool Home On Siesta Key. Separate In-law Suite Adds To The Appeal. Very Spacious And Warm, This Home Has Been Well Cared For By The Live-in Owner, Who Has Installed Many Upgrades Over The Years. In 2015, Owner Installed An 83 Ga...

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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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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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Listing data comes from My Florida Regional MLS.

Listing information last updated on February 14th, 2016 at 6:48am EST.