Siestas Bayside

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Overview

Siestas Bayside is the largest waterfront neighborhood on Siesta Key with 199 houses. There are a diverse selection of properties, from simple to extravagant. Boaters will find affordable options here on deep water canals.

Below are all of the homes for sale in the Siestas Bayside subdivision on Siesta Key, Florida. All real estate listings are updated daily from the Sarasota Multiple Listing Service (MLS).

To learn more about any of these properties or receive email updates when new listings hit the market, simply give us a call at 941-544-6467 or send us an email. We are here to help!

MLS® Listing Statistics

Total Listings: 9
Average Price: $2,373,000
Highest Price: $5,500,000
Lowest Price: $948,000
Average Size: 2,829 ft²
Average Price Per Square Foot: $765 per ft²

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Siestas Bayside

Homes for Sale in Siestas Bayside

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Image 0: A4672499

579 Commonwealth Lane, SARASOTA, FL - $5,500,000

Residential, Single Family Residence
  • 5 Beds
  • 6 Baths
  • 4,508 SQFT
  • 113 DOM
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Pre-construction. To Be Built. Welcome To A World Where Every Day Feels Like An Escape To Paradise! This Meticulously Crafted 4,500 Sq. Ft. Residence On Siesta Key Blends Contemporary Architecture With Earth Tones, Rich Natural Materials, And An U...

Image 1: A4589732

558 Venice Lane, SARASOTA, FL - $4,799,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,132 SQFT
  • 837 DOM
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Newly Complete And Move-in Ready! A Luxury, Coastal Contemporary Home On Siesta Key. Welcome To Your Future Coastal Retreat, Brought To Life By Heritage Builders, An Award-winning Custom Home Builder Known For Excellence In Design And Craftsmanshi...

Image 2: A4670452

910 Siesta Key Place, SARASOTA, FL - $3,000,000

Residential, Single Family Residence
  • 5 Beds
  • 5 Baths
  • 4,201 SQFT
  • 92 DOM
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Boater’s Dream On Siesta Key! Experience The Ultimate Waterfront Lifestyle In This Beautifully Renovated Siesta Key Home, Offering An Extraordinary 268 Feet Of Waterfront And Immediate Access To The Intracoastal Waterway. No Bridges To The Bay. Th...

Image 3: A4674684

4508 Woodside Road, SARASOTA, FL - $2,450,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,276 SQFT
  • 94 DOM
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Luxury Exclusive Living – Boaters’ Paradise Welcome To 4508 Woodside Rd., A True Waterfront Retreat On Siesta Key Offering Privacy, Boating Convenience, And Refined Coastal Living. Positioned On One Of The Deepest Canals On The Island, This Hom...

749 Tropical Circle, SARASOTA, FL - $1,575,000

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,598 SQFT
  • 97 DOM
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A Private Tropical Haven In The Heart Of Siesta Key, Beautifully Reimagined Coastal Retreat Tucked Away On Nearly Half An Acre In One Of Siesta Key’s Most Coveted Neighborhoods. This Stunning Four-bedroom, Two-and-a-half-bath Pool Home Lives Effor...

783 Birdsong Lane, SARASOTA, FL - $1,150,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,905 SQFT
  • 118 DOM
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Experience Coastal Living At Its Finest In This Turnkey-furnished, Three-bedroom, Two-bath Retreat Tucked Away On A Quiet Cul-de-sac In A Private Community Just Minutes From The Beach! This Home Features The Ultimate Outdoor Living Space With Nume...

Image 6: A4669940

630 Venice Lane, SARASOTA, FL - $975,000

Residential, Single Family Residence
  • 4 Beds
  • 2 Baths
  • 1,859 SQFT
  • 136 DOM
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One Or More Photo(s) Has Been Virtually Staged. Nestled Near The Gentle Waters Of Roberts Bay, This Enchanting Siesta Key Home Rests On A Quiet Cul De Sac Street Where The Only Sounds Are The Whisper Of Palms And The Laughter Of Neighbors Walking ...

711 Birdsong Lane, SARASOTA, FL - $960,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,730 SQFT
  • 347 DOM
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Located In The Heart Of Siesta Key, This Three-bedroom, Two-bath Home With A Two-car Garage Offers A Rare Opportunity To Experience Island Living Just One Mile From Siesta Key Beach—consistently Ranked The #1 Beach In The United States For Its Whi...

635 Tropical Circle, SARASOTA, FL - $948,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,255 SQFT
  • 135 DOM
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Discover Luxurious Coastal Living On Tropical Siesta Key, #1 Beach In The Us And #4 In The World! Set On An Elevated Lot That Sustained No Storm Damage, Includes A New Tamko Hurricane Proof Roof With Transferable Workmanship Warranty, New Gutters...

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on March 14th, 2026 at 5:08pm EDT.

Map of Siestas Bayside

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