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: 14
Average Price: $1,618,698
Highest Price: $4,999,777
Lowest Price: $795,000
Average Size: 2,063 ft²
Average Price Per Square Foot: $741 per ft²

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Entrance to Siesta Isles

Listings for Sale in Siesta Isles

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Image 0: A4656098

5569 Cape Leyte Drive, SARASOTA, FL - $4,999,777

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 3,654 SQFT
  • 3 DOM
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Location, Location, Location !!! Live Like A Lottery Winner On The Crystal Sands & Aqua Waters Of Siesta Key. Literally, You Can Walk One Block To Be With The Playful Dolphins At The #1 Beach In The Usa, Or Out Your Back Door, To Spend The Day On...

Image 1: A4639209

951 Contento St., SIESTA KEY, FL - $2,299,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,882 SQFT
  • 135 DOM
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Under Construction: Nestled In One Of Siesta Key’s Best-kept Secrets, The Coastal Haven Is Tucked Away In The Peaceful Privacy Of A Relaxing Cul-de-sac—away From The Hustle And Bustle, Offering You An Unmatched Retreat. This Stunning Property Boas...

Image 2: A4650938

1038 Contento Street, SARASOTA, FL - $1,725,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,217 SQFT
  • 47 DOM
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Siesta Key Canal Front Home With 175’ Of Sea Wall On The Grand Canal In The Desirable And Quaint Neighborhood Of Siesta Isles. Ride Your Bike To The Village Or The World-famous Siesta Key Beach Rated #1 In Usa. This Beautifully Well-kept 3 Bedro...

Image 3: A4636955

5560 Shadow Lawn Drive, SARASOTA, FL - $1,695,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,124 SQFT
  • 151 DOM
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New Price! Discover The Epitome Of Coastal Living With This Stunning Waterfront Home On Siesta Key, Steps From The World-famous White Sands Of Siesta Beach And The Aqua Waters Of The Gulf Of Mexico. On An Oversized 14,000-square-foot Corner Lot, T...

5581 Shadow Lawn Drive, SARASOTA, FL - $1,695,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,120 SQFT
  • 23 DOM
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Your Siesta Key Dream Starts Right Here! This Spectacular, Fully Renovated 4-bedroom, 3-bath Home In The Highly Sought-after Siesta Isles Community Is The Total Package—modern, Stylish, Move-in Ready, And Just A Short Walk To The World-famous Whit...

Image 5: A4650604

1014 Contento Street, SARASOTA, FL - $1,580,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 2,397 SQFT
  • 55 DOM
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Here's The Opportunity You Have Been Waiting For. Incredible Floor Plan With This Concrete Block Home. Large Bedrooms With Three On One Side And The Owner's Suite On The Other. Large In-home Laundry, Oversized Garage And A Corner Lot. Wonderful Pr...

Image 6: A4649470

5502 Shadow Lawn Drive, SARASOTA, FL - $1,389,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,337 SQFT
  • 60 DOM
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Build Your Dream Home Or Renovate The Existing Home On This Siesta Isles Canal Front Lot Just A Short Walk To The Cool Powdery Quartz Sands Of Siesta Key. This 14,200 Square Foot Lot Boasts Approximately 80 Feet On A Deep Canal With A Boat Dock. N...

5432 Cape Leyte Drive, SARASOTA, FL - $1,295,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,659 SQFT
  • 60 DOM
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Grab Your Sunglasses And Flip-flops, Because This Charming Siesta Key Retreat Is Just Minutes From World-famous Siesta Beach, The #1 Beach In The Usa! With Powdery White Sands And Crystal-clear, Turquoise Waters Right Around The Corner, Your Beach...

Image 8: A4656346

5572 Shadow Lawn Drive, SARASOTA, FL - $1,200,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,039 SQFT
  • 3 DOM
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Siesta Beach Here I Come! Waterfront Property Half A Mile To Siesta Beach. Welcome To 5572 Shadow Lawn Drive On Siesta Key. 3 Bedroom, 2 Bath Home With 102 Ft Frontage On The Grand Canal. One Fixed Bridge At Midnight Pass Rd Means Great Boating Ac...

734 Canal Road, SARASOTA, FL - $1,000,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,412 SQFT
  • 52 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 The Sought-after Community Of Siesta Isles, Just Two...

Image 10: A4642030

5525 Shadow Lawn Drive, SARASOTA, FL - $999,999

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,644 SQFT
  • 117 DOM
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With Just A Short Distance To The #1 Rated Beach In The Us, Siesta Key, This Location Is Perfect For An Island Lifestyle. Located In The Desirable Siesta Isles Community On A Large Lot With Over 13,000 Sf. Charming Brick Home With Three Bedrooms ...

5223 Shadow Lawn Drive, SARASOTA, FL - $995,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,459 SQFT
  • 27 DOM
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One Or More Photo(s) Has Been Virtually Staged. Elegant Siesta Key Retreat – 3-bed, 2-bath Pool Home With Preserve Views Discover An Exceptional Opportunity At 5223 Shadow Lawn Dr, A Refined 3-bedroom, 2-bathroom Residence In Siesta Isles On Si...

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 22nd, 2025 at 1:50pm 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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