Bay Island

Bay Island Real Estate for Sale – Sarasota, Florida 34242

Superlatives characterize Bay Island which is among the largest real estate developments on Siesta Key and one of the most popular spots to find Sarasota luxury waterfront homes for sale. Much of its popularity hinges on the unobstructed views of Sarasota Bay and Roberts Bay from this community of 169 single family homes located at the northeastern tip of Siesta Key.

It is most attractive to boat owners as Bay Island is surrounded by water deep enough to accommodate the keel of a large sailboat.

Now widely known as the gateway to Siesta Key, Bay Island was formerly directly connected to the barrier island. A 35-foot wide canal, however, was dug to separate it from Siesta Key in 1917 as part of the development of the 65-room Bay Island Hotel. Following the closure of this luxury hotel 1950s, Bay Island’s residential community began to flourish.

Distinctive ambience

To searchers of luxury Sarasota homes for sale, this community offers an endearing collection of large estate manors and beach-bungalow houses in traditional colonial style. All of these residences are located in generously sized parcels.

Siesta Drive bisects Bay Island into two sections, each having a distinct characteristic. Lush, mature foliage and trees dominate the southern section along Freeling Drive and Flamingo Avenue thereby exuding that laid-back old-Florida ambience. The northern section along Norsota Way is more expressive of the waterfront lifestyle with the sweeping panorama it affords of the Ringling Causeway Bridge and the downtown Sarasota skyline.

It is in this northern section where most of the larger Bay Island homes are located. The prime waterfront Sarasota homes for sale here typically have price tags which can hit the $5.3 million mark for a four-bedroom estate home with a floor area of slightly over 6,300 square feet. Sales-listed inland residences in this community can start under the million-dollar level as in a four-bedroom fixer-upper with a floor plan of 2,400 square feet with a quoted price in the high $600s.

Location’s great blessings

Year-round residents composed of retirees and professionals, along with seasonal snowbirds, comprise Bay Island’s population. In addition to the magnificent views and the boating haven it offers to its residents, this community is likewise prized for its great location. It serves not only as a gateway to the pristine white sands of Siesta Key but, as important, this community is the barrier island’s portal to the various attractions at downtown Sarasota.

Just across the Siesta Drive Bridge, for instance, are the merchants in and around Southside Village, including Saks Fifth Avenue, Morton’s Gourmet Market and the Publix Super Market in Paradise Plaza. The health care facilities of Sarasota Memorial Hospital and the life and leisure destinations at the city center are also just a few minutes’ drive from the Bay Island residences.

Bay Island Homes for Sale

Below are the current real estate listings available at the Bay Island

Please contact me if you would like to schedule a tour of any of the listed properties below.

MLS# A4601040 - Status: Active View Property Details Add to Favorites View Map

• 3799 FLAMINGO AVE
• Price: $19,950,000
• Zip Code: 34242
• 8138 Square Feet
• Subdivision: SIESTA KEY / BAY ISLAND
• Bedrooms: 4 Baths: 4+
• Discover 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 l ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4618500 - Status: Active View Property Details Add to Favorites View Map

• 3482 FLAMINGO AVE
• Price: $8,495,000
• Zip Code: 34242
• 5201 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 6 Baths: 6+
• An 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 you ... Read More
• Listing courtesy of: LIVING VOGUE LLC

MLS# A4610537 - Status: Active View Property Details Add to Favorites View Map

• 3550 FLAMINGO AVE
• Price: $7,200,000
• Zip Code: 34242
• 4711 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 4 Baths: 4+
• Under 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 bl ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4629840 - Status: Active View Property Details Add to Favorites View Map

• 3460 FLAMINGO AVE
• Price: $5,500,000
• Zip Code: 34242
• 1500 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 1 Baths: 1
• Exclusive 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 ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4632039 - Status: Active View Property Details Add to Favorites View Map

• 508 SIESTA DR
• Price: $3,200,000
• Zip Code: 34242
• 2943 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 3 Baths: 2+
• One 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-concre ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4630576 - Status: Active View Property Details Add to Favorites View Map

• 530 FREELING DR
• Price: $1,750,000
• Zip Code: 34242
• 2152 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 2 Baths: 2
• 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 terrazzo floors had storm damage and is p ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4629384 View Property Details Add to Favorites View Map

• 546 FREELING DR
• Price: $1,600,000
• Zip Code: 34242
• 0.27 Acres
• Incredible waterfront value. Bay Island is the premiere section on the north end of Siesta Key, a 10 minute drive to Southside Village shops and restaurants and 15 minutes to downtown or Siesta Village. Prized for its location, this canal front lot i ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4629683 - Status: Active View Property Details Add to Favorites View Map

• 3480 ANGLIN DR
• Price: $1,300,000
• Zip Code: 34242
• 1537 Square Feet
• Subdivision: BAY ISLAND PARK
• Bedrooms: 4 Baths: 3
• Prime Development Opportunity on Siesta Key - 3480 Anglin DriveThis double lot, spanning 16,200 square feet, is an ideal site for redevelopment. Located at the corner of Anglin Drive and Siesta Drive, this corner lot is 181 ft from Anglin Dr to Flami ... Read More
• Listing courtesy of: KELLER WILLIAMS ON THE WATER S