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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# A4675755 View Property Details Add to Favorites View Map

684 FREELING DR
Price: $9,900,000
Zip Code: 34242
1.48 Acres
Welcome 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 ... Read More
Listing courtesy of: KW COASTAL LIVING III

MLS# A4675752 - Status: Active View Property Details Add to Favorites View Map

684 FREELING DR
Price: $9,900,000
Zip Code: 34242
2548 Square Feet
Subdivision: BAY ISLAND
Bedrooms: 3 Baths: 3+
Welcome 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 ... Read More
Listing courtesy of: KW COASTAL LIVING III

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# A4673215 - Status: Active View Property Details Add to Favorites View Map

3820 FLAMINGO AVE
Price: $8,395,000
Zip Code: 34242
4775 Square Feet
Subdivision: BAY ISLAND
Bedrooms: 4 Baths: 4+
Under Construction. Incredible opportunity in highly desirable Bay Island, easy access to downtown Sarasota and Siesta beaches. Currently under construction with acclaimed Voigt Brothers construction, early 2027 completion date. Please request floor ... Read More
Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

3550 FLAMINGO AVE
Price: $6,595,000
Zip Code: 34242
4711 Square Feet
Subdivision: BAY ISLAND
Bedrooms: 4 Baths: 4+
BEST PRICED NEW CONSTRUCTION JUST BECAME BETTER PRICED!!!! 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 ... Read More
Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4669657 - Status: Active View Property Details Add to Favorites View Map

527 FREELING DR
Price: $5,825,000
Zip Code: 34242
4310 Square Feet
Subdivision: BAY ISLAND SHORES
Bedrooms: 4 Baths: 4+
Under Construction. The exterior presentation of this spectacular waterfront residence is most impressive with its blend of modern architecture and refined luxury. With superior elevation high above the water's edge on Siesta Key's prestigious Bay Is ... Read More
Listing courtesy of: GRECO REAL ESTATE

MLS# A4675757 - Status: Active View Property Details Add to Favorites View Map

684 FREELING DR
Price: $5,750,000
Zip Code: 34242
2548 Square Feet
Subdivision: BAY ISLAND
Bedrooms: 3 Baths: 3+
An extraordinary chance to own one of Sarasota's most coveted waterfront homesites, this 29,902-square-foot parcel offers an unparalleled setting for a custom estate on North Siesta Key. With 61 feet of water frontage along the pristine expanse of Ro ... Read More
Listing courtesy of: KW COASTAL LIVING III

MLS# A4675756 View Property Details Add to Favorites View Map

684 FREELING DR
Price: $5,750,000
Zip Code: 34242
0.68 Acres
An extraordinary chance to own one of Sarasota's most coveted waterfront homesites, this 29,902-square-foot parcel offers an unparalleled setting for a custom estate on North Siesta Key. With 61 feet of water frontage along the pristine expanse of Ro ... Read More
Listing courtesy of: KW COASTAL LIVING III

MLS# A4676577 View Property Details Add to Favorites View Map

843 NORSOTA WAY
Price: $5,499,000
Zip Code: 34242
0.37 Acres
Set along one of Siesta Key's most coveted bayfront streets, this exceptional property offers some of the most breathtaking views in all of Sarasota--spanning open water, the city skyline, and endlessly changing sunsets. Positioned in an enclave of m ... Read More
Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4676472 - Status: Active View Property Details Add to Favorites View Map

843 NORSOTA WAY
Price: $5,499,000
Zip Code: 34242
2467 Square Feet
Subdivision: BAY ISLAND
Bedrooms: 3 Baths: 2
Set along one of Siesta Key's most coveted bayfront streets, this exceptional property offers some of the most breathtaking views in all of Sarasota--spanning open water, the city skyline, and endlessly changing sunsets. Positioned in an enclave of m ... Read More
Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4674955 - Status: Active View Property Details Add to Favorites View Map

831 SIESTA DR
Price: $5,100,000
Zip Code: 34242
4250 Square Feet
Subdivision: BAY ISLAND
Bedrooms: 5 Baths: 4+
Pre-Construction. To be built. PROPOSED 4,250 SQ. FT. CUSTOM RESIDENCE .BUILD-TO-SUIT opportunity to create a bespoke coastal home with flexibility to tailor architecture, layout, finishes, and scale to a refined lifestyle.Located on Bay Island at th ... Read More
Listing courtesy of: IRVING GROUP INC

MLS# A4675751 View Property Details Add to Favorites View Map

620 FREELING DR
Price: $5,000,000
Zip Code: 34242
0.82 Acres
An extraordinary chance to own one of Sarasota's most coveted waterfront homesites, this 35,737-square-foot parcel offers an unparalleled setting for a custom estate on North Siesta Key. With 330 feet of water frontage along the pristine expanse of R ... Read More
Listing courtesy of: KW COASTAL LIVING III

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

749 FREELING DR
Price: $4,995,000
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# A4673685 - Status: Active View Property Details Add to Favorites View Map

878 FREELING DR
Price: $4,795,000
Zip Code: 34242
3866 Square Feet
Subdivision: BAY ISLAND SHORES
Bedrooms: 4 Baths: 4
Coastal Elegance on the Northern tip of Siesta Key. Discover timeless luxury in this waterfront estate nestled in the exclusive Bay Island enclave on Siesta Key's coveted North end. With panoramic views of Roberts Bay and the Intracoastal Waterway, t ... Read More
Listing courtesy of: WATERSIDE REALTY LLC

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# 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# A4673758 - Status: Active View Property Details Add to Favorites View Map

3455 ANGLIN DR
Price: $1,589,900
Zip Code: 34242
2558 Square Feet
Subdivision: BAY ISLAND PARK
Bedrooms: 3 Baths: 3+
Welcome to 3455 Anglin Drive, nestled in Siesta Key's highly sought-after Bay Island neighborhood. This beautifully renovated coastal home has been transformed from top to bottom since its last purchase--featuring a brand-new roof, a brand-new pool h ... Read More
Listing courtesy of: CORCORAN DWELLINGS REALTY

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

854 NORSOTA WAY
Price: $1,499,000
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