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: $1,920,556
Highest Price: $3,995,000
Lowest Price: $1,095,000
Average Size: 2,393 ft²
Average Price Per Square Foot: $795 per ft²

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Entrance to Siesta Isles

Listings for Sale in Siesta Isles

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Image 0: A4640177

927 Contento Street, SARASOTA, FL - $3,995,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,649 SQFT
  • 33 DOM
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Under Construction. Under Construction. Tidewater Builders Presents This Custom, Luxury Waterfront Property On Siesta Key's Grand Canal. With Easy Access To The Gulf Of Mexico And Just One Bridge To The Inter-coastal, This Is A Boater's Dream. A N...

Image 1: A4634690

5376 Shadow Lawn Drive, SARASOTA, FL - $2,500,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 3,721 SQFT
  • 44 DOM
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Move In Ready! Florida Living On Siesta Key. Located In Siesta Isles, A Community With 4 Miles Of Canal Front Saltwater Waterways With Access To Roberts Bay, The Intracoastal, And The Gulf Of Mexico. Tropical Setting Overlooking The Deep-water Ca...

Image 2: A4632863

5576 Contento Drive, SARASOTA, FL - $2,200,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,921 SQFT
  • 89 DOM
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Experience Exceptional Island Living At 5576 Contento Drive, Siesta Key, Florida. Nestled At The End Of The Cul-de-sac, The Home Has Sweeping Canal Views With 200 Feet Of Water Frontage, Offering A Concrete Seawall, Boat Lift, And Kayak Lift. This...

Image 3: A4636955

5560 Shadow Lawn Drive, SARASOTA, FL - $1,895,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,124 SQFT
  • 54 DOM
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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, This Four-b...

Image 4: A4639209

951 Contento St., SIESTA KEY, FL - $1,790,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 2,882 SQFT
  • 38 DOM
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Located In The Exclusive Siesta Isles Community, "the Coastal Haven" Is A Prime Property On Siesta Key, Offering Significant Waterfront And Large Pool. The Seller Has Signed A Contract For A Total Renovation Of The Deck And Pool, Which Is Estimate...

Image 5: A4634695

5402 Shadow Lawn Drive, SARASOTA, FL - $1,350,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,886 SQFT
  • 44 DOM
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Opportunity To Enjoy True Florida Living On Siesta Key In Beautiful Siesta Isles. This One Level Home Offers Nearly 1900 Sf Of Living Space Set On A 104' Wide Deep-water Canal Lot With Access To Roberts Bay, The Intracoastal And The Gulf Of Mexico...

Image 6: A4637970

5602 Cape Leyte Drive, SARASOTA, FL - $1,265,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,111 SQFT
  • 46 DOM
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Nestled In The Highly Sought-after Siesta Isle Neighborhood, This Exceptional 14,000+ Sq. Ft. Corner Lot Presents An Unparalleled Opportunity To Create Your Dream Home Just Steps From The Main Entrance Of World-renowned Siesta Key Beach. Whether Y...

5525 Shadow Lawn Drive, SARASOTA, FL - $1,195,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,644 SQFT
  • 20 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 ...

Image 8: A4635480

5353 Shadow Lawn Drive, SARASOTA, FL - $1,095,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,596 SQFT
  • 64 DOM
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With No Water Damage Or Water Intrusion, You Can Have Peace Of Mind That You Are Getting A Move In Ready Piece Of Tranquility On The Beautiful, World Renown Island Of Siesta Key. Being Offered Turnkey Finished Negotiable, You Are Ready To Move In ...

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 17th, 2025 at 7:34am 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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