Siesta Isles

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# A4617570 - Status: Active View Property Details Add to Favorites View Map

• 5531 CONTENTO DR
• Price: $2,300,000
• Zip Code: 34242
• 3653 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 5 Baths: 4
• One or more photo(s) has been virtually staged. The 3 storms caused only minor damage to fencing and pool cage screening. Miniscule amount of water in garage likely wind-blown. This beautifully designed residence offers the perfect blend of comfort a ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4632863 - Status: Active View Property Details Add to Favorites View Map

• 5576 CONTENTO DR
• Price: $2,200,000
• Zip Code: 34242
• 1921 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• 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 ex ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4630478 View Property Details Add to Favorites View Map

• 5537 CAPE LEYTE DR
• Price: $1,595,000
• Zip Code: 34242
• 0.35 Acres
• Once in a generation, an opportunity to acquire a remarkable waterfront location on Siesta Key may come your way.While waterfront properties come and go, few offer the additional amenities of this coveted street, Cape Leyte Drive, situated two blocks ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4630208 - Status: Active View Property Details Add to Favorites View Map

• 5537 CAPE LEYTE DR
• Price: $1,595,000
• Zip Code: 34242
• 2095 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• Once in a generation, an opportunity to acquire a remarkable waterfront location on Siesta Key may come your way.While waterfront properties come and go, few offer the additional amenities of this coveted street, Cape Leyte Drive, situated two blocks ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4626421 - Status: Active View Property Details Add to Favorites View Map

• 5569 SHADOW LAWN DR
• Price: $1,300,000
• Zip Code: 34242
• 2074 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• NEW BUILD OPPORTUNITY OR REHAB!!Take advantage of being in the heart of Sarasota | Siesta Key by keeping the original structure, and doing a complete renovation!You have a solid standing home that comes with PGT hurricane impact windows, preferred sl ... Read More
• Listing courtesy of: KELLER WILLIAMS ON THE WATER S

MLS# A4626371 View Property Details Add to Favorites View Map

• 5569 SHADOW LAWN DR
• Price: $1,300,000
• Zip Code: 34242
• 0.28 Acres
• NEW BUILD OPPORTUNITY. This oversized lot gives you 12,000 sqft to build your new luxurious home, right in the heart of Siesta Key Florida. You are on a quiet street that can take you off of the island with ease, straight into the village for casual ... Read More
• Listing courtesy of: KELLER WILLIAMS ON THE WATER S

MLS# A4628681 - Status: Active View Property Details Add to Favorites View Map

• 5624 CAPE LEYTE DR
• Price: $1,250,000
• Zip Code: 34242
• 2550 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 4 Baths: 3
• RARE LOCATION! Rare opportunity to live just five houses from the street entrance to famed Siesta Key public beach. No need for a car or to worry about parking. Just a 5 minute walk and you'll be enjoying the beautiful quartz sand and crystal clear ... Read More
• Listing courtesy of: SILVER PALM REALTY