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!
| 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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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...
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...
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...
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...
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...
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...
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 ...
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...
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...
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 ...
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...
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...
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.
