Despite Siesta Key being one of the most attractive housing markets in Southwest Florida, few house hunters become aware of Siestas Bayside Waterside. This subdivision is located in the northern part of the barrier island, but its four neighborhoods are hidden behind lush foliage and vegetation; for this reason, not many home buyers find the great real estate opportunities available herein.
Siestas Bayside Waterside in Siesta Key, Florida, offers a mix of historic charm and modern luxury. Some residences retain the classic Florida ranch-style design from the early 1970s, along with charming beach cottages, while others showcase Mediterranean, Key West, and Caribbean architectural influences. Regardless of style, all homes in this secluded neighborhood offer privacy, thanks to lush native vegetation and the peaceful setting along the Grand Canal.
As of 2025, home prices in Siestas Bayside Waterside have appreciated significantly. Current listings range from approximately $799,000 to $5,399,000. For example:
- A 3-bedroom, 2-bathroom home with 1,453 square feet is listed for $799,000.
- A 4-bedroom, 3.5-bathroom home with 2,641 square feet is priced at $2,299,000.
- A luxurious 4-bedroom, 4.5-bathroom estate with 4,007 square feet is on the market for $5,399,000.
Latest pricing at Siestas Bayside Waterside Siesta Key Florida will be found below if there is inventory.
With increasing demand and rising property values, Siesta Bayside Waterside continues to be a highly sought-after community, offering a blend of historic appeal and modern waterfront living.
Living at Siestas Bayside Waterside means being able to take a short walk to the whitest sandy beaches in the world. Boating, fishing and scuba diving are some of the most popular activities among residents. Beach taverns and restaurants can be found along the Intracoastal Waterway and neighboring barrier islands. Downtown Sarasota and its numerous suburban comforts are just a short drive away down a scenic causeway.
Many families consider moving to Siesta Key and enrolling their children in one of the private academies on the island. School-age residents are served by Phillippi Shores Elementary, Brookside Middle and Riverview High.
Siestas Bayside Waterside Siesta Key Florida Homes for Sale
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(all data current as of
4/29/2025)
Listing information deemed reliable but not guaranteed. Read full disclaimer.
