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: 13
Average Price: $2,064,000
Highest Price: $5,500,000
Lowest Price: $599,000
Average Size: 2,571 ft²
Average Price Per Square Foot: $725 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
  • 23 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 - $4,985,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,132 SQFT
  • 747 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
  • 36 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 - $2,690,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,238 SQFT
  • 3 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 H...

Image 4: A4672419

518 Venice Lane, SARASOTA, FL - $2,295,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 2,676 SQFT
  • 24 DOM
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Elegant Siesta Key Waterfront Retreat - Welcome To A Truly Distinguished Canal-front Residence, Where Timeless Design Meets The Effortless Beauty Of Waterfront Living. Set Beneath Majestic Oaks And Tropical Landscaping, The Canopied Circular Paver...

Image 5: A4673529

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

Residential, Single Family Residence
  • 4 Beds
  • 3 Baths
  • 2,598 SQFT
  • 7 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...

Image 6: A4670981

567 Venice Lane, SARASOTA, FL - $1,150,000

Residential, Single Family Residence
  • 4 Beds
  • 2 Baths
  • 1,915 SQFT
  • 38 DOM
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Under The Canopy Of Grand Oaks And Banyan Trees, This Move-in-ready Furnished Siesta Key Pool Home Offers The Perfect Blend Of Luxury And Coastal Charm. Located Minutes From The World-famous Beach And Village, This Retreat Has Been Redesigned For ...

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

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 1,905 SQFT
  • 28 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 8: A4668594

635 Tropical Circle, SARASOTA, FL - $1,129,000

Residential, Single Family Residence
  • 3 Beds
  • 2 Baths
  • 2,255 SQFT
  • 53 DOM
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Discover Luxurious Coastal Living On Tropical Siesta Key, #1 Beach In The Us And #4 In The World! You Will Love This Beautifully Updated 3-bedroom, 2-bath Single-level Residence Offering Nearly 2,300 Sq. Ft. Of Refined Comfort. Perfectly Situated...

630 Venice Lane, SARASOTA, FL - $1,000,000

Residential, Single Family Residence
  • 4 Beds
  • 2 Baths
  • 1,859 SQFT
  • 46 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
  • 257 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...

Image 11: A4668505

4894 Oxford Drive, SARASOTA, FL - $799,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 1,831 SQFT
  • 57 DOM
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Pool Home!! Priced To Sell!! Nestled On The Peaceful Tranquil Island Of Siesta Key, Renowned For Its World-class Beach And Romantic Sunsets. Just Minutes From Siesta Beach & Village. This Is The Most Wonderful Place To Embrace Island-style Livin...

Image 12: A4654692

782 Birdsong Lane, SARASOTA, FL - $599,000

Residential, Single Family Residence
  • 2 Beds
  • 2 Baths
  • 1,577 SQFT
  • 193 DOM
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Opportunity Knocks In One Of The Most Sought-after Locations On Siesta Key! Roof In Good Shape And Impact Windows Throughout The Home. This Prime Property Offers The Perfect Chance To Create Your Ideal Coastal Retreat. Situated Just Moments From W...

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 December 14th, 2025 at 10:13am EST.

Map of Siestas Bayside

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