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# A4179116 - Status: Active View Property Details Add to Favorites View Map

  • 900 CONTENTO CIR
  • Price: $1,375,000
  • Zip Code: 34242
  • 2506 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 4
  • Calming water views from every room in this home, except one bedroom. This is the key lot, at the end of a cul-de-sac street boasting 188 platted feet of canal frontage. The recapped seawall has two concrete docks. Plenty of water frontage if you wan ... Read More
  • Listing courtesy of: RE/MAX Alliance Group

MLS# A4204474 - Status: Active View Property Details Add to Favorites View Map

  • 803 PARADISE WAY
  • Price: $1,100,000
  • Zip Code: 34242
  • 2460 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 3
  • Welcome to Paradise! Don't miss this mid century waterfront retreat a quick boat ride to the Intracoastal Waterway situated on an 18,555 square foot cul de sac lot! Tropical landscaping welcome you to your Siesta Key oasis a short walk or bike ride f ... Read More
  • Listing courtesy of: RE/MAX Alliance Group

MLS# A4207008 - Status: Active View Property Details Add to Favorites View Map

  • 5633 CAPE LEYTE DR
  • Price: $1,095,000
  • Zip Code: 34242
  • 2228 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 3
  • Incredible Location!! You can't get much closer to Siesta Key Beach - (Voted the #1 beach in the US!) - and have 101 feet of wonderful boating water on the GRAND CANAL!! Don't miss this beautiful and well cared for home boasting four bedrooms (split ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4203969 - Status: Active View Property Details Add to Favorites View Map

  • 5439 AZURE WAY
  • Price: $1,074,900
  • Zip Code: 34242
  • 2473 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • Escape to Siesta Key in this dazzling waterfront residence only moments from the top-rated beach in the United States. Located on deep boating water, Siesta's Grand Canal, arrive home by land or by sea. Light, bright, and beautiful, this three-bedroo ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4186488 - Status: Active View Property Details Add to Favorites View Map

  • 5440 AZURE WAY
  • Price: $1,070,000
  • Zip Code: 34242
  • 2252 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 2
  • Boating! Beach! Pool! This spacious Siesta Key home has it all! Nicely situated on an extra large corner lot ,one can't help but notice the lush landscaping upon approaching the front door. Once inside, the split plan, 3 bedroom 2 bath home has an up ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4194405 - Status: Active View Property Details Add to Favorites View Map

  • 5507 CONTENTO DR
  • Price: $1,035,000
  • Zip Code: 34242
  • 1802 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • Don't let the size fool you-this waterfront home has it all! Enter through the custom-made front door to the newly renovated interior. Finished with high-quality products and tasteful design, this is the perfect house for your Siesta Key lifestyle. ... Read More
  • Listing courtesy of: Key Solutions Real Estate Grp

MLS# A4194719 - Status: Active View Property Details Add to Favorites View Map

  • 5515 CONTENTO DR
  • Price: $999,900
  • Zip Code: 34242
  • 2233 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 2
  • One of the most captivating views of the Grand Canal you will find in Siesta Isles. The gardens provide enchanting sitting areas, walk ways and a Selby Garden type atmosphere. The roof is a metal roof that looks like tile, the seawall is triple enfor ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4201714 - Status: Active View Property Details Add to Favorites View Map

  • 5563 SHADOW LAWN DR
  • Price: $749,000
  • Zip Code: 34242
  • 2384 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • OPPORTUNITY AWAITS! This Siesta Isles Oasis has two great options: Either make it a perfect vacation rental that can bring in excess of $100,000 per year (Source VRBO) or make it your dream home! It is located just a short walk from Siesta Key Beach; ... Read More
  • Listing courtesy of: Helpusell Gulf Coast

MLS# A4185721 - Status: Active View Property Details Add to Favorites View Map

  • 1008 GLEBE LN
  • Price: $699,900
  • Zip Code: 34242
  • 2557 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 2+
  • A tropical oasis awaits you just minutes from Siesta Key Beach, the #1 Beach in the US! This beautiful and bright Key West Style residence is the essence of island living. The fresh and modern updates give the home the charm and function of a careful ... Read More
  • Listing courtesy of: RE/MAX Platinum Realty

MLS# A4206928 - Status: Active View Property Details Add to Favorites View Map

  • 5542 CAPE AQUA DR
  • Price: $695,000
  • Zip Code: 34242
  • 1591 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 2
  • This Siesta Isles house is ideally located on a quiet cul-de-sac and just a short distance to the #1 beach in the USA, Siesta Key Beach. Private access to Beach Road runs behind the house. Lovingly maintained and updated with a split floor plan, this ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY