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# A4687147 - Status: Active View Property Details Add to Favorites View Map

• 546 FREELING DR
• Price: $12,500,000
• Zip Code: 34242
• 4353 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 5 Baths: 5+
• Pre-Construction. To be built. Discover an extraordinary opportunity to own an expansive double lot of 0.52 acres on North Siesta Key with this single-story, new construction transitional modern-style luxury home by Pham Development. Offering 170 fee ... Read More
• Listing courtesy of: PHAM REALTY GROUP LLC

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# 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# A4690268 - Status: Active View Property Details Add to Favorites View Map

• 847 FREELING DR
• Price: $3,950,000
• Zip Code: 34242
• 4034 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 4 Baths: 4+
• Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides ... Read More
• Listing courtesy of: COMPASS FLORIDA LLC

MLS# A4668843 View Property Details Add to Favorites View Map

• 894 FREELING DR
• Price: $3,750,000
• Zip Code: 34242
• 0.26 Acres
• Zoning confirmation letter in from City of Sarasota. Ready for permitting and your custom dream home. This waterfront gem fronts Roberts Bay, facing Edwards Island, and offers unobstructed 180-degree views of dolphins, various bird species, and manat ... Read More
• Listing courtesy of: GRECO REAL ESTATE

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

• 732 SIESTA DR
• Price: $2,995,000
• Zip Code: 34242
• 3743 Square Feet
• Subdivision: BAY ISLAND SHORES
• Bedrooms: 3 Baths: 4+
• Rare and extraordinary waterfront offering on the coveted North end of Siesta Key, this premier Bay Island estate parcel presents the ultimate canvas for creating a world-class coastal retreat. Set on nearly half an acre, the property commands sweepi ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4683447 - Status: Active View Property Details Add to Favorites View Map

• 3458 ANGLIN DR
• Price: $2,595,000
• Zip Code: 34242
• 2513 Square Feet
• Subdivision: BAY ISLAND PARK
• Bedrooms: 4 Baths: 2+
• Welcome to Bay Island, ideally positioned on the north end of Siesta Key, where island living meets exceptional convenience. Just moments from Siesta Beach, Siesta Key Village, and downtown Sarasota's waterfront dining and cultural offerings--with ea ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

• 854 NORSOTA WAY
• Price: $1,399,000
• 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# A4675479 View Property Details Add to Favorites View Map

• 3473 HAMILTON AVE
• Price: $979,900
• Zip Code: 34242
• 0.29 Acres
• Some spend years searching for the perfect spot. This is it. A rare buildable lot on Bay Island--known as the gateway to Siesta Key, this intimate 169-home neighborhood at the northern tip of Siesta Key, surrounded by deep turquoise waters and just m ... Read More
• Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE

MLS# O6399340 - Status: Active View Property Details Add to Favorites View Map

• 749 SIESTA DR
• Price: $750,000
• Zip Code: 34242
• 1978 Square Feet
• Subdivision: BAY ISLAND
• Bedrooms: 4 Baths: 2
• Investor Special!!Welcome to your next amazing project! Known damage with full or partial rehab. Excellent renovation opportunity on an oversized lot in a highly desirable Siesta Key area. Sold AS-IS with significant upside potential. ... Read More
• Listing courtesy of: EXP REALTY LLC