Siesta Isles Homes

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Overview

Location:
Middle of the Island
Age of Homes:
1960 to 2008
Number of Homes:
295
Size Range:
1189 to 4756 square feet
Price Range:
$625,000s to $1.35 Million

To learn more about any of the properties in Siesta Isles or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!

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MLS® Listing Statistics

Total Listings: 9
Average Price: $2,537,667
Highest Price: $4,795,000
Lowest Price: $995,000
Average Size: 2,555 ft²
Average Price Per Square Foot: $965 per ft²

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Entrance to Siesta Isles

Listings for Sale in Siesta Isles

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Image 0: A4695248

5572 Shadow Lawn Drive, SARASOTA, FL - $4,795,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,523 SQFT
  • 1 DOM
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Under Construction. An Exceptional Opportunity To Own A Brand-new Waterfront Residence In The Highly Sought-after Siesta Isles Community. Expertly Crafted By Nutter Custom Construction, This British West Indies-inspired Custom Home Offers 3,568 Sq...

Image 1: A4685577

5569 Cape Leyte Drive, SARASOTA, FL - $4,495,000

Residential, Single Family Residence
  • 5 Beds
  • 4 Baths
  • 3,654 SQFT
  • 85 DOM
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Location, Location, Location !!! One Block To The Crystal Sands Of Siesta Key Beach The #1 Beach In The Usa! Or Spend The Day On The Aqua Waters With Two Boats On Lifts Out Back, And 119' Of Frontage On The Grand Canal Leading To The Icw (only...

Image 2: A4694937

813 Idlewild Way, SARASOTA, FL - $3,795,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 4,161 SQFT
  • 3 DOM
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Tucked Away Near The End Of A Quiet Cul-de-sac On An Oversized, Private Waterfront Lot In Siesta Isles With 109 Feet Of Frontage On Siesta Key's Grand Canal, This Exceptional 4,161-square-foot Residence Offers A Rare Combination Of Privacy, Expans...

Image 3: TB8483961

814 Paradise Way, SARASOTA, FL - $1,995,000

Residential, Single Family Residence
  • 4 Beds
  • 2 Baths
  • 1,996 SQFT
  • 91 DOM
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Exceptional Siesta Key Waterfront Residence Offering A Rare Opportunity To Own A Turn-key, Move-in-ready 4 Bedrooms And 2 Bathrooms Home In One Of The Island’s Most Desirable And Tranquil Locations. Situated On A Quiet Cul-de-sac Along A Grand Can...

Image 4: A4684955

951 Contento St., SIESTA KEY, FL - $1,890,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,882 SQFT
  • 86 DOM
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New Low Price And Potential Seller Financing! Deep Boating Water On The Grand Canal And Siesta Key’s World-famous Beaches Just Minutes Away, Experience The Best Of Island Living. This Beautifully Renovated Three-bedroom, Three-bath Waterfront Resi...

Image 5: A4683288

5507 Contento Drive, SARASOTA, FL - $1,775,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 1,788 SQFT
  • 105 DOM
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A Boater's Dream! Welcome To Your Siesta Key Waterfront Dream Home On A Third Of An Acre Lot! Private Dock With A 7,000lb Boat Lift On A Wide Part Of The Grand Canal! Move Right In And Start Enjoying The Island Lifestyle! This Home Features Great ...

Image 6: W7883717

742 Edgemere, SIESTA KEY, FL - $1,700,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,454 SQFT
  • 89 DOM
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Build Or Renovate Discover An Exceptional Waterfront Opportunity In The Coveted Siesta Isles Neighborhood On Siesta Key. Situated On An Oversized Lot At The Intersection Of Two Canals, This Property Offers 118 Feet Of Seawall, Wide Water Views,...

Image 7: A4636955

5560 Shadow Lawn Drive, SARASOTA, FL - $1,399,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,124 SQFT
  • 497 DOM
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One Of The Lowest Priced Homes On Siesta Key's Deep Boating Water And Only 3 Blocks To The White Quartz Sand And Aqua Gulf Waters! An Inviting Opportunity To Enjoy Relaxed Waterfront Living On Siesta Key, This Well-maintained Residence Is Ideally ...

734 Canal Road, SARASOTA, FL - $995,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,412 SQFT
  • 135 DOM
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Endless Possibilities Just Two Blocks From Siesta Beach! Whether You're Looking To Remodel The Structure Or Build A New Island Retreat, Opportunity Awaits. A Prime 12,229-square-foot Property In Sought-after Community Of Siesta Isles, Just Two Blo...

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 DBA Stellar MLS.

Listing information last updated on June 6th, 2026 at 8:52pm EDT.

Siesta Isles Description (continued)

Community Information

Residents of Siesta Isles love the terrific location close to the world-famous Siesta Key Beach. In addition, the Village is only a short walk or bike ride away for dining, shopping and entertainment.

The neighborhood is filled with lush, tropical vegetation. Architectural styles include older ranch style and newer Mediterranean designs. Many of the houses are located on canals with boat access.

Map of Siesta Isles

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