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# A4667008 - Status: Active View Property Details Add to Favorites View Map

• 5362 SHADOW LAWN DR
• Price: $4,950,000
• Zip Code: 34242
• 4294 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 3+
• Experience elevated coastal living in this award-winning "Marlin Model" by Nutter Custom Construction, perfectly positioned on Siesta Key's coveted Grand Canal. Completed in 2023 and showcased as the builder's signature home, this completely custom Y ... Read More
• Listing courtesy of: NCC PROPERTIES LLC

MLS# A4685577 - Status: Active View Property Details Add to Favorites View Map

• 5569 CAPE LEYTE DR
• Price: $4,495,000
• Zip Code: 34242
• 3654 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 5 Baths: 4
• LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage on the Grand Canal leading to the ICW (only one br ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4684955 - Status: Active View Property Details Add to Favorites View Map

• 951 CONTENTO ST.
• Price: $2,000,000
• Zip Code: 34242
• 2882 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 3
• Deep boating water on the Grand Canal and Siesta Key's world-famous beaches just minutes away, experience the best of island living. This beautifully renovated three-bedroom, three-bath waterfront residence offers a peaceful island retreat with nearl ... Read More
• Listing courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY

MLS# TB8483961 - Status: Active View Property Details Add to Favorites View Map

• 814 PARADISE WAY
• Price: $1,995,000
• Zip Code: 34242
• 1996 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 4 Baths: 2
• Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island's most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, ... Read More
• Listing courtesy of: COMMUNITY REALTY ASSOCIATES

MLS# A4683288 - Status: Active View Property Details Add to Favorites View Map

• 5507 CONTENTO DR
• Price: $1,775,000
• Zip Code: 34242
• 1788 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 3
• A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying the island lifestyle! This home features great wat ... Read More
• Listing courtesy of: PREFERRED SHORE LLC

MLS# W7883717 - Status: Active View Property Details Add to Favorites View Map

• 742 EDGEMERE
• Price: $1,750,000
• Zip Code: 34242
• 1454 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• Build or RenovateDiscover an exceptional waterfront opportunity in the coveted Siesta Isles neighborhood on Siesta Key. Situated on an oversized lot at the intersection of two canals, this property offers 118 feet of seawall, wide water views, and di ... Read More
• Listing courtesy of: LISTWITHFREEDOM.COM

MLS# A4688348 View Property Details Add to Favorites View Map

• 5448 AZURE WAY
• Price: $1,750,000
• Zip Code: 34242
• 0.33 Acres
• Discover an exceptional waterfront homesite in the heart of Siesta Key, one of Florida's sought-after coastal destinations. On a quiet, no-through-traffic cul-de-sac in the exclusive Siesta Isles enclave, this cleared lot offers a rare island-within- ... Read More
• Listing courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY

MLS# A4670108 - Status: Active View Property Details Add to Favorites View Map

• 5569 CONTENTO DR
• Price: $1,749,000
• Zip Code: 34242
• 1772 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 2 Baths: 2
• SIESTA KEY ~ UPDATED PRICING WITH OWNER FINANCING OPTION ~ Siesta Isles Neighborhood ~ 123' Water-Frontage ~ Close To Siesta Key Beach ~ Home Updated Throughout (Inside - Outside) ~ Oversized Lot: 12,000+ Square Feet ~ Pool ~ Two Boat Docks With Lift ... Read More
• Listing courtesy of: RE/MAX ALLIANCE GROUP

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

• 5560 SHADOW LAWN DR
• Price: $1,549,000
• Zip Code: 34242
• 2124 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 4 Baths: 3
• Siesta Key Waterfront Living--Priced to Embrace the Island LifestyleAn inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this beautifully maintained residence is ideally positioned just moments from the powdery white sands of Sie ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

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# A4679533 - Status: Active View Property Details Add to Favorites View Map

• 1002 GLEBE LN
• Price: $1,095,000
• Zip Code: 34242
• 1808 Square Feet
• Subdivision: SIESTA ISLES
• Bedrooms: 3 Baths: 2
• New price! Beautifully remodeled and ideally just minutes from world-renowned white sands of Siesta Beach, this chic island pool home offers an exceptional blend of style, comfort, and storm-ready peace of mind. Designed for effortless coastal living ... Read More
• Listing courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY

MLS# A4675607 - Status: Active View Property Details Add to Favorites View Map

• 734 CANAL RD
• Price: $995,000
• 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 sought-after community of Siesta Isles, just two blocks ... Read More
• Listing courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY