Siesta Isles in Siesta Key : Homes for Sale in a Waterfront Community

The Siesta Key housing market has more to offer athan imposing beachfront condo towers; if you are looking for a quiet residential setting where you can enjoy boating, fishing and raising a family, Siesta Isles is highly recommended. Located between Hidden Harbor Road and Beach Road, Siesta Isles in Siesta Key is a large neighborhood that tourists do not get to see unless they venture to explore beyond the public beaches.  Initially developed in the 1960s, Siesta Isles is a feat of engineering that initially involved years of dredging for the purpose of creating deepwater canals connecting to Roberts Bay.

Siesta Isles evokes an ambiance that combines Old Florida charm with the feeling of a Caribbean resort. With a four-mile network of canals, nearly three-quarters of all properties are guaranteed waterfront views or private docking space. If you see a listing with a Contento Street or Azure way address, you can be assured of waterfront property because those two roads are within islands.

Unlike other subdivisions in Siesta Key, the homes at Siesta Isles enjoy generous home sites measuring between 12,000 and 16,000 square feet. Architectural styles range from Florida ranches built in the late 1960s to remodeled properties that have been turned into Mediterranean revival estates. Pricing starts at $595K for a two-bedroom Florida ranch located just a block away from a canal and three blocks from the beach. Once you start looking at waterfront homes with private docking space, covered swimming pool, and three bedrooms, you can find prices below $800K, which is very reasonable when considering the location.

To get an idea of how close boaters are to Roberts Bay and the Intracoastal Waterway, even those living in the southern section of Siesta Isles can exit Siesta Key in about 20 minutes. Residents who live on the bay side of the neighborhood can walk to the beach in 10 minutes, and this is how long it takes to the restaurants, pubs and neighborhood markets along Ocean Boulevard. For more comprehensive shopping, driving to the Publix supermarket at Sarasota Pavilion takes about 11 minutes. The Downtown Sarasota arts and culture districts are just 15 minutes away.

Homes for Sale at Siesta Isles in Siesta Key

See all Siesta Isles Siesta Key Homes for Sale.
(all data current as of 5/12/2025)

Listing information deemed reliable but not guaranteed. Read full disclaimer.