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# A4653658 - Status: Active View Property Details Add to Favorites View Map

• 3799 FLAMINGO AVE
• Price: $18,500,000
• Zip Code: 34242
• 8138 Square Feet
• Subdivision: SIESTA KEY / BAY ISLAND
• Bedrooms: 4 Baths: 4+
• Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished do ... Read More
• Listing courtesy of: DOUGLAS ELLIMAN

MLS# A4639066 View Property Details Add to Favorites View Map

• 3821 FLAMINGO AVE
• Price: $8,450,000
• Zip Code: 34242
• 1.52 Acres
• Exquisite Bay Island Estate Parcel Available. Build your dream waterfront estate on this exceptional 1.52-acre bayfront estate lot, offering both open bay access and a protected deep-water slip on Hansen Bayou. The east side of this extremely private ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

• 3550 FLAMINGO AVE
• Price: $6,795,000
• Zip Code: 34242
• 4711 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 4 Baths: 4+
• READY FOR OCCUPANCY. CONSTRUCTION COMPLETED. LOWEST NEW CONSTRUCTION price on highly desirable North Siesta Key. 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 block construc ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4666354 - Status: Active View Property Details Add to Favorites View Map

• 749 FREELING DR
• Price: $5,749,000
• Zip Code: 34242
• 6827 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 4 Baths: 4+
• Welcome to Casa Della Fontana -- The Fountain House. Nestled on the tranquil north end of Siesta Key, this gated waterfront estate is a blend of seaside serenity, architectural distinction, and lifestyle luxury. Perched on a deep, sailboat-accessible ... Read More
• Listing courtesy of: DOUGLAS ELLIMAN

MLS# A4662402 - Status: Active View Property Details Add to Favorites View Map

• 3607 FLAMINGO AVE
• Price: $4,950,000
• Zip Code: 34242
• 3876 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 4 Baths: 4
• One or more photo(s) has been virtually staged. Exceptional Waterfront - North Siesta Key's Bay Island Boater's Dream - Exerience the best of coastal living in this elegant 4bd/4ba residence - just minutes to the Intracoastal Waterway. The home featu ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4668843 View Property Details Add to Favorites View Map

• 894 FREELING DR
• Price: $4,675,000
• Zip Code: 34242
• 0.26 Acres
• This waterfront gem fronts Roberts Bay, facing Edwards Island, and offers unobstructed 180-degree views of dolphins, various bird species, and manatees. It's a perfect canvas for creating your customized residence. Located on the prized northern tip ... Read More
• Listing courtesy of: GRECO REAL ESTATE

MLS# A4667093 - Status: Active View Property Details Add to Favorites View Map

• 810 SIESTA DR
• Price: $3,995,000
• Zip Code: 34242
• 4622 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 3 Baths: 3+
• Look no further. Welcome home to your coastal Siesta Key waterfront retreat, a boater's dream come true. On the desired north end of Siesta Key, this four-bedroom, four-bath residence spans 4,622 square feet of meticulously designed living space. Ele ... Read More
• Listing courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY

MLS# A4658014 - Status: Active View Property Details Add to Favorites View Map

• 838 NORSOTA WAY
• Price: $3,650,000
• Zip Code: 34242
• 3001 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 5 Baths: 5+
• Pre-Construction. To be built. 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 sophistication with c ... Read More
• Listing courtesy of: THE STUTZMAN REALTY GROUP, LLC

MLS# A4640849 - Status: Active View Property Details Add to Favorites View Map

• 732 SIESTA DR
• Price: $3,500,000
• Zip Code: 34242
• 3743 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 3 Baths: 4+
• Extraordinary waterfront property with expansive Intracoastal Waterway views located on the sought after north end of Siesta Key. Now is the perfect opportunity to build your dream waterfront estate on this exceptional almost one-half acre lot in Bay ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4661788 View Property Details Add to Favorites View Map

• 428 SIESTA DR
• Price: $3,200,000
• Zip Code: 34242
• 0.48 Acres
• Waterfront boating access, zoned mixed use and multi family in city limits that allow weekly rentals. Build dream home with 3 boat lifts (16,000#, 8,000#, 4,500#) Build a family compound where everyone has their space. ... Read More
• Listing courtesy of: BLUESRQ REAL ESTATE INC

MLS# A4661294 - Status: Active View Property Details Add to Favorites View Map

• 428 SIESTA DR
• Price: $3,200,000
• Zip Code: 34242
• 2163 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 2 Baths: 2
• Rare opportunity on prime boating water on Bay Isle. This property offers over one hundred feet of canal frontage, a composite dock, and three boat lifts (16,000#,8000# & 4500#) ensuring seamless access to the water with no bridges to the intracoasta ... Read More
• Listing courtesy of: BLUESRQ REAL ESTATE INC

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

• 508 SIESTA DR
• Price: $2,499,000
• 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# A4667778 - Status: Active View Property Details Add to Favorites View Map

• 546 FREELING DR
• Price: $1,850,000
• Zip Code: 34242
• 3996 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 4 Baths: 4+
• Pre-Construction. To be built. Boating access and large lot opportunity. This rare 11,884 sq.ft. lot on Siesta Key offers a unique opportunity to build your dream home in one of the most sought-after areas. Fit up to a 42-foot boat on the private doc ... Read More
• Listing courtesy of: PHAM REALTY GROUP LLC

MLS# A4665123 - Status: Active View Property Details Add to Favorites View Map

• 854 NORSOTA WAY
• Price: $1,625,000
• Zip Code: 34242
• 1667 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 2 Baths: 2
• Welcome to your dream family home on Bay Island, located on the premier north end of Siesta Key. This inviting 2-bedroom, 2-bathroom residence is nestled among beautiful homes on Norsota Way, one of Sarasota's most coveted streets, offering a perfect ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4669400 View Property Details Add to Favorites View Map

• 3721 FLAMINGO AVE
• Price: $1,395,000
• Zip Code: 34242
• 0.26 Acres
• North Siesta Key. Build your dream home on this prime waterfront lot on desired Bay Island, the gateway to Siesta Key and one of the island's exclusive communities. The 11,458-square-foot corner lot offers lush landscaping, and a tranquil lagoon/cana ... Read More
• Listing courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY

MLS# A4667437 - Status: Active View Property Details Add to Favorites View Map

• 3721 FLAMINGO AVE
• Price: $1,395,000
• Zip Code: 34242
• 2628 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 3 Baths: 3
• Restore a piece of architectural history or build your dream home on this prime waterfront lot on Bay Island, the gateway to Siesta Key and one of the island's exclusive communities. Designed by renowned architect Ben Baldwin, a leading figure in the ... Read More
• Listing courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY

MLS# A4667033 View Property Details Add to Favorites View Map

• 838 NORSOTA WAY
• Price: $1,175,000
• Zip Code: 34242
• 0.32 Acres
• Welcome to this beautiful piece of land that is offered in the middle of this great community and street on Norsota Way. This land offers walking distance to the North Bridge, a golf cart ride to the Siesta key village, and the luxury of fine dining ... Read More
• Listing courtesy of: PHAM REALTY GROUP LLC