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# A4640177 - Status: Active View Property Details Add to Favorites View Map

• 927 CONTENTO ST
• Price: $3,995,000
• Zip Code: 34242
• 3649 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 4 Baths: 3+
• 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 new, ... Read More
• Listing courtesy of: PREFERRED SHORE LLC

MLS# A4639209 - Status: Active View Property Details Add to Favorites View Map

• 951 CONTENTO ST.
• Price: $2,299,000
• Zip Code: 34242
• 2882 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 4
• 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 boasts ... Read More
• Listing courtesy of: COLDWELL BANKER SARASOTA CENT.

MLS# A4634690 - Status: Active View Property Details Add to Favorites View Map

• 5376 SHADOW LAWN DR
• Price: $2,200,000
• Zip Code: 34242
• 3721 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 4 Baths: 4+
• BRING ALL THE FAMILY - MOVE IN READY! Florida living on this high & dry lot on Siesta Key. Your own private tropical deep-water canal frontage. Large saltwater pool and spa, private screened courtyard adjacent to a large game room and theater room - ... Read More
• Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE

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# A4650938 - Status: Active View Property Details Add to Favorites View Map

• 1038 CONTENTO ST
• Price: $1,725,000
• Zip Code: 34242
• 2217 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• 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 bedroom, ... Read More
• Listing courtesy of: SARASELLSSARASOTA.COM

MLS# A4636955 - Status: Active View Property Details Add to Favorites View Map

• 5560 SHADOW LAWN DR
• Price: $1,695,000
• Zip Code: 34242
• 2124 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 4 Baths: 3
• 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, this ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4650604 - Status: Active View Property Details Add to Favorites View Map

• 1014 CONTENTO ST
• Price: $1,580,000
• Zip Code: 34242
• 2397 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 4 Baths: 2+
• 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 priva ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4649470 - Status: Active View Property Details Add to Favorites View Map

• 5502 SHADOW LAWN DR
• Price: $1,399,000
• Zip Code: 34242
• 2337 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 4
• 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. New ... Read More
• Listing courtesy of: PREFERRED SHORE LLC

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# A4649500 - Status: Active View Property Details Add to Favorites View Map

• 5432 CAPE LEYTE DR
• Price: $1,295,000
• Zip Code: 34242
• 1659 Square Feet
• Subdivision: SIESTA ISLES UNIT 2
• Bedrooms: 3 Baths: 2
• 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 ge ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4642030 - Status: Active View Property Details Add to Favorites View Map

• 5525 SHADOW LAWN DR
• Price: $1,195,000
• Zip Code: 34242
• 1644 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• 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 and ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4651051 - Status: Active View Property Details Add to Favorites View Map

• 734 CANAL RD
• Price: $1,000,000
• Zip Code: 34242
• 1412 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• 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 bl ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4650975 View Property Details Add to Favorites View Map

• 734 CANAL RD
• Price: $1,000,000
• Zip Code: 34242
• 0.28 Acres
• Endless possibilities just two blocks from Siesta Beach! Whether you're looking to build a new island retreat or remodel the existing structure, opportunity awaits, a prime 12,229-square-foot property in the sought-after community of Siesta Isles, ju ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY