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+
• Move right in and start living the dream--this awe-inspiring, turn-key furnished estate (with the exception of select artwork and personal items) is a private, gated peninsula on the north end of the world-famous Siesta Key. Spanning over an acre wit ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4640787 - Status: Active View Property Details Add to Favorites View Map

• 684 FREELING DR
• Price: $11,000,000
• 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# A4640164 View Property Details Add to Favorites View Map

• 684 FREELING DR
• Price: $11,000,000
• 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# 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: EXP REALTY LLC

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# A4639638 - Status: Active View Property Details Add to Favorites View Map

• 679 NORSOTA WAY
• Price: $8,250,000
• Zip Code: 34242
• 3788 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 3 Baths: 4
• Set 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 squa ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4638900 View Property Details Add to Favorites View Map

• 679 NORSOTA WAY
• Price: $8,250,000
• Zip Code: 34242
• 0.66 Acres
• Prime waterfront property located on the prestigious north end of Siesta Key. Nestled along coveted Norsota Way, this exceptional double lot boasts 150 feet of deep-water bay frontage--a rare find in a neighborhood where most properties offer just 10 ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

• 3550 FLAMINGO AVE
• Price: $7,400,000
• 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# A4640158 View Property Details Add to Favorites View Map

• 620 FREELING DR
• Price: $6,250,000
• 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# A4632580 - Status: Active View Property Details Add to Favorites View Map

• 749 FREELING DR
• Price: $5,950,000
• Zip Code: 34242
• 6827 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 4 Baths: 4+
• Experience 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 co ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4643447 - Status: Active View Property Details Add to Favorites View Map

• 684 FREELING DR
• Price: $5,500,000
• 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# A4640154 View Property Details Add to Favorites View Map

• 684 FREELING DR
• Price: $5,500,000
• 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# A4633793 View Property Details Add to Favorites View Map

• 3460 FLAMINGO AVE
• Price: $5,500,000
• Zip Code: 34242
• 1.28 Acres
• Exclusive waterfront opportunity on Siesta Key to build your waterfront estate. Discover the pinnacle of waterfront living with this gated, estate-sized 1.27-acre property on wonderful Bay Island at the desirable north end of Siesta Key. This excepti ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

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# A4637922 View Property Details Add to Favorites View Map

• 894 FREELING DR
• Price: $5,250,000
• Zip Code: 34242
• 0.26 Acres
• Fronting Roberts Bay, This rare jewel is all about the view and the location. It provides a canvas for a bayfront estate in a neighborhood known for its exclusivity and high real estate values. Imagine your very own enchanting residence customized to ... Read More
• Listing courtesy of: GRECO REAL ESTATE

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

• 508 SIESTA DR
• Price: $2,950,000
• 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# A4638309 - Status: Active View Property Details Add to Favorites View Map

• 3445 ANGLIN DR
• Price: $2,450,000
• Zip Code: 34242
• 2772 Square Feet
• Subdivision: BAY ISLAND PARK
• Bedrooms: 3 Baths: 3
• Nestled 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 be ... Read More
• Listing courtesy of: WILDFLOWER REAL ESTATE LLC

MLS# A4637567 - Status: Active View Property Details Add to Favorites View Map

• 3721 FLAMINGO AVE
• Price: $2,300,000
• Zip Code: 34242
• 2628 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 3 Baths: 3
• Once 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 the ... Read More
• Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4638005 - Status: Active View Property Details Add to Favorites View Map

• 3455 ANGLIN DR
• Price: $1,500,000
• Zip Code: 34242
• 2558 Square Feet
• Subdivision: BAY ISLAND PARK
• Bedrooms: 3 Baths: 3+
• INVESTOR'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 (1 ... Read More
• Listing courtesy of: NEW DOOR REAL ESTATE LLC

MLS# A4638234 View Property Details Add to Favorites View Map

• 624 NORSOTA WAY
• Price: $1,400,000
• Zip Code: 34242
• 0.48 Acres
• SIESTA 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 ... Read More
• Listing courtesy of: WHITE SANDS REALTY GROUP FL

MLS# A4635011 - Status: Active View Property Details Add to Favorites View Map

• 624 NORSOTA WAY
• Price: $1,400,000
• Zip Code: 34242
• 2854 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 4 Baths: 3
• SIESTA 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 ... Read More
• Listing courtesy of: WHITE SANDS REALTY GROUP FL