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: 11
Average Price: $2,191,636
Highest Price: $5,395,000
Lowest Price: $995,000
Average Size: 2,258 ft²
Average Price Per Square Foot: $925 per ft²

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Entrance to Siesta Isles

Listings for Sale in Siesta Isles

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Image 0: A4667008

5362 Shadow Lawn Drive, SARASOTA, FL - $5,395,000

Residential, Single Family Residence
  • 3 Beds
  • 5 Baths
  • 4,294 SQFT
  • 102 DOM
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Experience Elevated Coastal Living In This Award-winning “marlin Model” By Nutter Custom Construction, Perfectly Positioned On Siesta Key’s Coveted Grand Canal. Completed In 2023 And Showcased As The Builder’s Signature Home, This Completely Custo...

Image 1: A4685577

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

Residential, Single Family Residence
  • 5 Beds
  • 4 Baths
  • 3,654 SQFT
  • 1 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: TB8483961

814 Paradise Way, SARASOTA, FL - $2,100,000

Residential, Single Family Residence
  • 4 Beds
  • 2 Baths
  • 1,996 SQFT
  • 7 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 3: A4684955

951 Contento St., SIESTA KEY, FL - $2,000,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,882 SQFT
  • 2 DOM
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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 Residence Offers A Peaceful Island Retreat With Ne...

Image 4: A4683288

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

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 1,788 SQFT
  • 22 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 5: W7883717

742 Edgemere, SIESTA KEY, FL - $1,750,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,454 SQFT
  • 5 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 6: A4670108

5569 Contento Drive, SARASOTA, FL - $1,749,000

Residential, Single Family Residence
  • 2 Beds
  • 2 Baths
  • 1,772 SQFT
  • 135 DOM
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Siesta Key ~ Updated Pricing With Owner Financing Option ~ Siesta Isles Neighborhood ~ 123' Water-frontage ~ Close To Siesta Key Beach ~ Home Updated Throughout (inside - Outside) ~ Oversized Lot: 12,000+ Square Feet ~ Pool ~ Two Boat Docks With L...

Image 7: A4636955

5560 Shadow Lawn Drive, SARASOTA, FL - $1,549,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,124 SQFT
  • 413 DOM
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Siesta Key Waterfront Living—priced To Embrace The Island Lifestyle An Inviting Opportunity To Enjoy Relaxed Waterfront Living On Siesta Key, This Beautifully Maintained Residence Is Ideally Positioned Just Moments From The Powdery White Sands ...

Image 8: A4649500

5432 Cape Leyte Drive, SARASOTA, FL - $1,150,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,659 SQFT
  • 324 DOM
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Exceptional Opportunity On Siesta Key. Now Offered At A Newly Adjusted Price, This Charming Siesta Key Retreat Presents An Outstanding Opportunity To Own Just Minutes From World-famous Siesta Beach—consistently Ranked Among The Best Beaches In The...

1002 Glebe Lane, SARASOTA, FL - $1,150,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,808 SQFT
  • 36 DOM
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Beautifully Remodeled And Ideally Just Minutes From World-renowned White Sands Of Siesta Beach, This Chic Island Pool Home Offers An Exceptional Blend Of Style, Comfort And Storm-ready Peace Of Mind. Designed For Effortless Coastal Living, The Ope...

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

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,412 SQFT
  • 51 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 March 14th, 2026 at 4:08pm 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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