Bay Island at Siesta Key Browse listings at Bay Island on Siesta Key. Featured1 / 16$950,0004BEDS3TOTAL BATHS1,537SQFT3480 ANGLIN DRIVE SARASOTA, FL 34242Single Family Residence For Sale- PendingUnder contract-accepting backup offers. Prime Development Opportunity on Siesta Key – 3480 Anglin Drive This double lot, spanning 16,200 square feet, is an ideal site for redevelopment in the city of Sarasota, lending to weekly rentals for newly con1 / 52$19,950,0004BEDS6TOTAL BATHS8,138SQFT3799 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveDiscover your very own gated private peninsula on world-famous Siesta Key. Located on the north end of the island, this one-of-a-kind awe-inspiring furnished estate sits on more than an acre with over 700 waterfront feet. A custom-designed driveway lNew Listing - a week on site1 / 30$11,000,0003BEDS4TOTAL BATHS2,548SQFT684 FREELING DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveWelcome to the most exclusive waterfront offering in Sarasota—an extraordinary canvas for a visionary estate. Set on nearly 1.5 acres with an unrivaled 400 feet of water frontage overlooking the pristine expanse of Roberts Bay, this North Siesta Key 1 / 98$8,495,0006BEDS7TOTAL BATHS5,201SQFT3482 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveAn elegant, private entrance shaded by regal palms and vibrant bougainvillea guides you toward something extraordinary. As the wrought iron gate closes behind you, fervent anticipation builds. Your dream home awaits. A tranquil fountain serenades youNew Listing - a week on site1 / 30$8,250,0003BEDS4TOTAL BATHS3,788SQFT679 NORSOTA WAY SARASOTA, FL 34242Single Family Residence For Sale- ActiveSet on one of the most coveted streets on Siesta Key, this beautifully crafted 1926 Spanish-style home sits on a double lot with 150 feet of deep-water bay frontage, significantly larger than most properties’ 100 feet of frontage. Spanning 3,788 squa1 / 8$7,200,0004BEDS5TOTAL BATHS4,711SQFT3550 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveUnder Construction. LOWEST NEW CONSTRUCTION price on highly desireable North Siesta Key and a completion date February 2025. Situated on 1/3 acre with 102 feet of wide canal waterfront and no bridges to the bay. The 4,711 square foot home is solid bl1 / 70$5,950,0004BEDS5TOTAL BATHS6,827SQFT749 FREELING DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveExperience coastal elegance and ultimate island living in this extraordinary gated waterfront estate, Casa della Fontana, the Fountain House. This home offers the ideal blend of luxury, privacy, and convenience on a tranquil street on Siesta Key's co1 / 31$5,500,0001BED1TOTAL BATH1,500SQFT3460 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveExclusive waterfront opportunity on Siesta Key. Discover the pinnacle of waterfront living with this gated, estate-sized 1.27-acre property located on highly coveted Bay Island at the desirable north end of Siesta Key. This exceptional property is a Price Change - 2 weeks ago1 / 57$2,950,0003BEDS3TOTAL BATHS2,943SQFT508 SIESTA DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveOne or more photo(s) has been virtually staged. Experience the ultimate in coastal living with this two-story residence in the highly desirable Bay Island Shores on the world-renowned Siesta Key. Located in a prime waterfront setting, this all-concreNew Listing - 2 weeks on site1 / 57$2,650,0003BEDS3TOTAL BATHS2,772SQFT3445 ANGLIN DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveNestled in the highly sought-after neighborhood of Bay Island, on Siesta Key's north end, this beautifully updated Key West style home offers the perfect blend of historic charm and modern convenience. The spacious, split floor plan features three beNew Listing - a week on site1 / 2$2,300,0003BEDS3TOTAL BATHS2,628SQFT3721 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- ActiveOnce in a lifetime opportunity to Restore a One-of-A-Kind Ben Baldwin Mid-Century Modern home. Architect and Designer Ben Baldwin was recognized internationally as the leading force in the Modern Movement of American Design and Architecture. Over the1 / 27$2,300,0003BEDS4TOTAL BATHS3,162SQFT3532 FLAMINGO AVENUE SARASOTA, FL 34242Single Family Residence For Sale- PendingUnder contract-accepting backup offers. Exceptional Waterfront Property on Siesta Key – A Boater’s Dream nestled on the north end of Siesta Key. Set on over 71 feet of prime seawall frontage along the pristine Hudson Bayou—one of Siesta Key’s cleares1 / 38$1,750,0002BEDS2TOTAL BATHS2,152SQFT530 FREELING DRIVE SARASOTA, FL 34242Single Family Residence For Sale- PendingUnder contract-accepting backup offers. Beautiful value for premier Bay Island waterfront property on the prized north end of Siesta Key and a short drive to downtown Sarasota and Siesta beaches. Sad to say that this mid-century modern home with tNew Listing - 4 weeks on site1 / 20$1,700,0003BEDS3TOTAL BATHS2,837SQFT527 FREELING DRIVE SARASOTA, FL 34242Single Family Residence For Sale- PendingUnder contract-accepting backup offers. Dreaming of waterfront living on Siesta Key? This rare and exclusive Bay Island property is your chance to create the home of your dreams while basking in one of Sarasota's most prized locations. With an impresNew Listing - 4 weeks on site1 / 27$1,500,0003BEDS4TOTAL BATHS2,558SQFT3455 ANGLIN DRIVE SARASOTA, FL 34242Single Family Residence For Sale- ActiveINVESTOR'S DREAM!!!! On Siesta Key's coveted Bay Island awaits this former beauty. It needs almost a full rehab to be restored to its former glory after recent hurricane damage, but the major components, such as the HVAC (4 years) and water heater (1New Listing - 4 weeks on site1 / 72$1,400,0004BEDS3TOTAL BATHS2,854SQFT624 NORSOTA WAY SARASOTA, FL 34242Single Family Residence For Sale- ActiveSIESTA KEY OPPORTUNITY - BUILD YOUR NEW HOME ON THIS 21,000+ SF LOT! The 1920s structures on this lot sustained storm damage – PROPERTY IS BEING SOLD FOR THE LAND VALUE ONLY – JUST IMAGINE THE DREAM HOME YOU COULD BUILD ON A LOT THAT’S JUST SHY OF A 1 / 14$895,0003BEDS2TOTAL BATHS2,182SQFT838 NORSOTA WAY SARASOTA, FL 34242Single Family Residence For Sale- PendingUnder contract-accepting backup offers. NEW BUILD OPPORTUNITY in Bay Island on quiet north Siesta Key street with minimal traffic to and from the mainland. Home damaged from storms. Being sold for LAND VALUE ONLY. Sizable rectangular lot of .32 acre.See All Results