Siesta Isles

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Siesta Isles Homes for Sale

Siesta Isles is a waterfront development made up of two small man made islands in the center of Siesta Key just north of Siesta Key Beach. Before this real estate was developed, the center of Siesta Key was extremely low and any storm surge would not have the means to recede. Though the canals that surround the community do provide limited access to the Intracoastal Waterway for small watercraft, the primary function of these canals was to provide the earth needed to raise the level of the home sites and to act as a means of drainage for the island in the event of a storm surge.

There are 295 homes in Siesta Isles, many with swimming pools and screened-in lanais. Most of the Siesta Isles homes were built in the 1960’s and 70’s and are primarily Florida Ranch designs that were very popular during that era. Prices for the homes in the community range from $400,000 for the smaller residences to nearly $2 million for the newer and larger homes. The residences located in Siesta Isles can be found on Azure Way, Contento Street, Shadow Lawn Way, Cape Leyte Drive, Idlewild Way, and Cape Aqua Drive.

At the Great International White Sand Beach Challenge held in 1987, Siesta Key Beach was recognized as having the whitest and finest sand in the world. The Siesta Isles homes located on the southern end of the community are within walking distance to this amazing beach, the rest of the homes are within a short bike ride.

Being centrally located, residents of Siesta Isles are close to the best of everything Siesta Key has to offer. From the fine restaurants and beach nightlife found in Siesta Key Village to the amazing white sandy beaches found on the island, Siesta Isles is close to it all. As a result of the “moat” that surrounds these castles, the community is tranquil and extremely safe.


Siesta Isles Real Estate for Sale

Below are all of the current real estate listings available for sale in Siesta Isles.

Please contact me if you would like to schedule a tour of any of the listed properties.

MLS# A4577033 - Status: Active View Property Details Add to Favorites View Map

  • 927 CONTENTO ST
  • Price: $4,449,000
  • Zip Code: 34242
  • 3649 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 3+
  • 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 new, raised seawall has ... Read More
  • Listing courtesy of: PREFERRED SHORE

MLS# A4578028 - Status: Active View Property Details Add to Favorites View Map

  • 816 EDGEMERE LN
  • Price: $2,750,000
  • Zip Code: 34242
  • 4214 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 4+
  • New pricing! Experience the pinnacle of modern coastal living in this extraordinary four-bedroom-plus-office, four-and-a-half-bath waterfront residence. Ideally located on Siesta Key, on the deep boating water of the Grand Canal, nestled on an oversi ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4576796 - Status: Active View Property Details Add to Favorites View Map

  • 5613 CAPE LEYTE DR
  • Price: $2,100,000
  • Zip Code: 34242
  • 2752 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 2
  • One or more photo(s) has been virtually staged. Incredible Price! Prime location extending nearly 100 Feet along the deep waters of the Grand Canal. The 3-bedroom, 2-bath residence sits on nearly a 1/3 OF AN ACRE and only ONE BLOCK to the powdery sa ... Read More
  • Listing courtesy of: WATERSIDE REALTY LLC

MLS# A4600114 - Status: Active View Property Details Add to Favorites View Map

  • 5455 AZURE WAY
  • Price: $2,000,000
  • Zip Code: 34242
  • 2732 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 4
  • Welcome to your dream waterfront home in the highly coveted Siesta Isles canal community is a prime location of Siesta Key. Where you will experience the tranquility of this coastal neighborhood which is its own Island within an Island features many ... Read More
  • Listing courtesy of: WILLIAM RAVEIS REAL ESTATE

MLS# A4611334 - Status: Active View Property Details Add to Favorites View Map

  • 5515 CONTENTO DR
  • Price: $1,895,000
  • Zip Code: 34242
  • 2223 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • The moment you step into this home it presents itself with a tastefully done interior decor and captivating views of a large basin on the Grand Canal. This Coastal island neighborhood is unique since all the homes are nestled on the water! Take a 3.5 ... Read More
  • Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4573857 - Status: Active View Property Details Add to Favorites View Map

  • 730 EDGEMERE LN
  • Price: $1,650,000
  • Zip Code: 34242
  • 1520 Square Feet
  • Subdivision: SIESTA ISLES UNIT 1A
  • Bedrooms: 3 Baths: 2
  • Paradise found! Here is your opportunity to own your own private oasis on Siesta Key. Believed to be originally designed/built by the historic icon, Ruth Richmond, this beautiful waterfront home is situated on the Grand Canal and is just one bridge a ... Read More
  • Listing courtesy of: COMPASS FLORIDA LLC

MLS# A4602135 - Status: Active View Property Details Add to Favorites View Map

  • 5544 CONTENTO DR
  • Price: $1,550,000
  • Zip Code: 34242
  • 1944 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 2
  • Siesta Key Waterfront Opportunity. BEACH & BOAT! A beautiful long view down the canal. Almost 2000 SF, this well maintained 3/2 home located in the highly desirable Siesta Isles is just waiting for you to call it your own. The kitchen and one bathroo ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE