Siesta Isles

Listings For SaleSold History and Market Report

 

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# A4157847 - Status: Active View Property Details Add to Favorites View Map

  • 5332 SHADOW LAWN DR
  • Price: $2,197,500
  • Zip Code: 34242
  • 4085 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 4+
  • Brand New...Award winning Allegra Homes new construction. British West Indies inspired located on the coveted Grand Canal of Siesta Key. Enjoy a waterfront lifestyle of boating and the beach. A deep water idle ride out the canal into Sarasota Bay and ... Read More
  • Listing courtesy of: Michael Saunders & Company

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# A4188259 - Status: Active View Property Details Add to Favorites View Map

  • 5303 CAPE LEYTE DR
  • Price: $1,295,000
  • Zip Code: 34242
  • 2563 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 3
  • The best of both worlds! Beach and Boating! This stylish waterfront 4 bedroom home on a large corner lot with long canal views, is a short boat ride to the ICW and just blocks to Siesta Beach! Spacious single story split plan interior, plus roomy out ... Read More
  • Listing courtesy of: Coldwell Banker Res R E

MLS# A4194354 - Status: Active View Property Details Add to Favorites View Map

  • 810 PARADISE WAY
  • Price: $1,200,000
  • Zip Code: 34242
  • 2916 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 4 Baths: 3+
  • Welcome to Paradise! Don't miss this updated waterfront retreat a quick boat ride to the Intracoastal Waterway. Situated on one of the best cul de sac lots in Siesta Isles, rich tropical lighted landscaping & lovely brick circular drive welcome you t ... Read More
  • Listing courtesy of: RE/MAX Alliance Group

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

  • 5440 AZURE WAY
  • Price: $1,095,000
  • 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: $1,075,000
  • Zip Code: 34242
  • 1867 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • Don't let 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. N ... 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: $1,050,000
  • 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# A4176964 - Status: Active View Property Details Add to Favorites View Map

  • 1046 CONTENTO ST
  • Price: $999,000
  • Zip Code: 34242
  • 2857 Square Feet
  • Subdivision: SIESTA ISLES UNIT 8
  • Bedrooms: 4 Baths: 2+
  • Wow - reduced $151,000! Boating and the beach! Truly the best value on Siesta Key. Spacious, updated four-bedroom, two-and-a-half-bath waterfront home with direct bay access is your perfect island getaway with plenty of room for guests. The floor pla ... Read More
  • Listing courtesy of: Premier Sothebys Intl Realty

MLS# A4176469 - Status: Active View Property Details Add to Favorites View Map

  • 908 CONTENTO CIR
  • Price: $899,999
  • Zip Code: 34242
  • 2554 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • LOWEST PRICED WATERFRONT IN SIESTA ISLES ON THE GRAND CANAL! SIESTA KEY LIVING!! 10 MINUTE WALK TO SIESTA KEY PUBLIC BEACH FROM THIS WATERFRONT BEAUTY. 2 MASTER SUITES PLUS A 3RD BEDROOM AND 3 BATHS. 125 FT SEAWALL, DOCK & FLOATING DOCK AND KAYAK RAM ... Read More
  • Listing courtesy of: ENRIGHT REALTY INC

MLS# A4187750 - Status: Active View Property Details Add to Favorites View Map

  • 5563 SHADOW LAWN DR
  • Price: $799,900
  • Zip Code: 34242
  • 2384 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • Shaded by a beautiful mature Grand Oak this timeless home is a One-of-a-Kind opportunity to take an existing gem and make it into your own Masterpiece. Two individual bedrooms, a separate Master Suite and a total of three full baths, a spacious eat ... Read More
  • Listing courtesy of: Waterside Realty LLC

MLS# A4193961 - Status: Active View Property Details Add to Favorites View Map

  • 5315 SHADOW LAWN DR
  • Price: $774,900
  • Zip Code: 34242
  • 2271 Square Feet
  • Subdivision: SIESTA ISLES
  • Bedrooms: 3 Baths: 3
  • Situated in beloved Siesta Isles, just a short distance from the No. 1 ranked beach in the United States, this three-bedroom residence is brimming with charm, personality and comfort. Set on an oversized, fenced lot, lush foliage sets the scene for t ... Read More
  • Listing courtesy of: Michael Saunders & Company

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

  • 1008 GLEBE LN
  • Price: $767,000
  • 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# A4137140 - Status: Active View Property Details Add to Favorites View Map

  • 5327 SHADOW LAWN DR
  • Price: $698,000
  • Zip Code: 34242
  • 2252 Square Feet
  • Subdivision: SIESTA ISLES UNIT 5
  • Bedrooms: 4 Baths: 3
  • Charming 4 bedroom 3 bath pool home on Siesta Key. Separate In-Law suite adds to the appeal. Very spacious and warm, this home has been well cared for by the live-in owner, who has installed many upgrades over the years. In 2015, owner installed a ... Read More
  • Listing courtesy of: A YOUNG REALTY GROUP INC