Bay Island at Siesta Key Browse listings at Bay Island on Siesta Key. Featured1 / 89$8,600,0004BEDS6TOTAL BATHS5,456SQFT700 FREELING DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveSWEEPING PANORAMIC WATER VIEWS!....MULTIPLE BOAT LIFTS!... GATED ESTATE RETREAT!...A Singular Offering Where PRIVACY and the Enjoyment of Waterfront Island Living create a Sanctuary of Grandeur where Memories are waiting to be made....Deep Sailboat W1 / 87$17,650,0004BEDS6TOTAL BATHS8,138SQFT3799 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveFour Seasons Hotel in Bali or private estate? Set on more than an acre of coveted waterfront property along the prestigious north end of Siesta Key, this extraordinary Balinese-inspired estate is a rare sanctuary where timeless architecture, unparallNew Listing - 7 days on site1 / 32$12,500,0005BEDS7TOTAL BATHS4,353SQFT546 FREELING DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActivePre-Construction. To be built. Expected to be complete in 3–4 months. Discover an extraordinary opportunity to own a new construction waterfront residence on an expansive 0.52-acre double lot on North Siesta Key. Designed and built by Pham Developmen1 / 25$8,750,0004BEDS6TOTAL BATHS4,775SQFT3820 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveUnder Construction. Move in before the 2026 holidays. Absolute best value for new construction on N Siesta Key in prime Bay Island location with easy access to downtown Sarasota or Siesta Key Beaches. High quality finishes, 130 ft of water frontage wNew Listing - 4 days on site1 / 100$6,975,0006BEDS7TOTAL BATHS4,373SQFT3482 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveSome homes are defined by their architecture, others by their setting. Casa Flamingo is a rare convergence of both, offering a distinctive vision of waterfront living on the coveted north end of Siesta Key. Set across nearly an acre of lush grounds, New Listing - 2 weeks on site1 / 24$4,950,0003BEDS4TOTAL BATHS3,876SQFT3607 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveExceptional Waterfront in North Siesta Key's Bay Island Shores Community. Experience the best of coastal living in this custom built residence with direct access just minutes to the Intracoastal Waterway. The home features a 2023 14,000lb dock/lift wNew Listing - 3 weeks on site1 / 19$4,190,0005BEDS7TOTAL BATHS3,001SQFT838 NORSOTA WAY SARASOTA, FL 34242Single Family Residence For Sale- ActiveUnder Construction. To be complete in a few months. Discover timeless coastal elegance in this upcoming traditional-style new construction home, perfectly situated in the highly coveted Bay Island neighborhood on Siesta Key. Designed to blend modern 1 / 29$3,950,0004BEDS5TOTAL BATHS4,034SQFT847 FREELING DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveLocated in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location providesOpen House Sun, Nov 15, 1 PM1 / 66$3,750,0005BEDS6TOTAL BATHS4,536SQFT604 NORSOTA WAY SARASOTA, FL 34242Single Family Residence For Sale- ActiveWelcome to an exceptional newly renovated residence in the highly coveted Bay Island neighborhood on north Siesta Key, where timeless coastal architecture and modern luxury come together in one of Siesta Key’s most desirable locations. Situated on an1 / 75$2,550,0003BEDS5TOTAL BATHS3,743SQFT732 SIESTA DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveBack on the market with a $445,000 price reduction, Rare and extraordinary waterfront offering on the coveted North end of Siesta Key, this premier Bay Island estate parcel presents the ultimate canvas for creating a world-class coastal retreat. Set New Listing - 3 weeks on site1 / 64$2,495,0004BEDS3TOTAL BATHS2,513SQFT3458 ANGLIN DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveLocated in the highly desirable Bay Island neighborhood, this beautifully updated, move-in-ready Key West-style residence offers an appealing combination of privacy, space, and convenience. Known as the "Gateway to Siesta Key," Bay Island enjoys a pr1 / 13$1,900,0003BEDS4TOTAL BATHS2,470SQFT3455 ANGLIN DRIVE SARASOTA, FL 34242Single Family Residence For Sale- Active Under ContractUnder contract-accepting backup offers. Experience the best of coastal living at this beautifully remodeled home in the heart of Siesta Key! Ideally located just minutes from the world-famous Siesta Key Beach, this inviting property blends modern elePrice Change - 3 weeks ago1 / 5$599,0004BEDS2TOTAL BATHS1,978SQFT749 SIESTA DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveAuction Property. This property has been identified for auction and the seller will transition the property to an auction if not under contract by the deadline of Nov 20th. Please make all offers by Nov 19th and the seller will consider all offers. SSee All Results