Bay Island

Listings For SaleSold History and Market Report

Bay Island Real Estate for Sale – Sarasota, Florida 34242

Bay Island

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

Bay Island

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

Bay Island

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# A4534680 - Status: Active View Property Details Add to Favorites View Map

  • 4001 FLAMINGO AVE
  • Price: $12,600,000
  • Zip Code: 34242
  • 7487 Square Feet
  • Subdivision: BAY ISLAND REP 01
  • Bedrooms: 5 Baths: 4+
  • Under Construction. Experience the majestic, private waterfront setting of this dazzling residence on Siesta Key with an approximate completion date of December 2022. Boasting 128' of water frontage along Roberts Bay, you'll delight in a tropical bac ... Read More
  • Listing courtesy of: COMPASS FLORIDA LLC

MLS# A4552060 - Status: Active View Property Details Add to Favorites View Map

  • 799 FREELING DR
  • Price: $10,000,000
  • Zip Code: 34242
  • 7636 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 4 Baths: 3+
  • Welcome to Vivre Le Rve (Living The Dream), a one-of-a-kind estate situated on one of the most desirable streets on Bay Island at the north end of Siesta Key. The Freeling Drive Peninsula is sited on one of Sarasota's most protected and most beautifu ... Read More
  • Listing courtesy of: PREFERRED SHORE

MLS# A4546740 - Status: Active View Property Details Add to Favorites View Map

  • 3722 FLAMINGO AVE
  • Price: $6,500,000
  • Zip Code: 34242
  • 4985 Square Feet
  • Subdivision: BAY ISLAND/SIESTA KEY
  • Bedrooms: 5 Baths: 5+
  • Pre-Construction. To be built. A dream home built by well-respected Voigt Brothers Construction on 95 ft of water frontage. Great boating waters on Hanson Bayou with easy access and no bridges to the bay. The home itself will be 4985 sqft with an ele ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4543853 - Status: Active View Property Details Add to Favorites View Map

  • 3810 FLAMINGO AVE
  • Price: $3,900,000
  • Zip Code: 34242
  • 3960 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 4 Baths: 3+
  • Revel in the spectacular Siesta Key lifestyle in one of Sarasota's finest neighborhoods with luxury homes that redefine island living. With serenity and privacy, along with easy big water access, you'll feel right at home in this fully furnished spra ... Read More
  • Listing courtesy of: KELLER WILLIAMS ON THE WATER

MLS# A4539684 - Status: Active View Property Details Add to Favorites View Map

  • 746 SIESTA DR
  • Price: $3,900,000
  • Zip Code: 34242
  • 4434 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 6 Baths: 3+
  • Looking for your dream home in Siesta Key or a one-in-a-million opportunity to own an amazing investment property in an area that has the potential to net $400+K net income per year? Look no further! Step into this beautiful world, where you can enjo ... Read More
  • Listing courtesy of: KELLER WILLIAMS ON THE WATER

MLS# A4543285 - Status: Active View Property Details Add to Favorites View Map

  • 3532 FLAMINGO AVE
  • Price: $3,649,000
  • Zip Code: 34242
  • 3162 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 3 Baths: 3+
  • A boater's dream offering 70ft of shoreline on the Hanson Bayou. A unique combination of sophistication and luxury awaits you in the quaint neighborhood of Bay Island. Enjoy watching dolphins play in your backyard! Conveniently located on the north ... Read More
  • Listing courtesy of: EXIT KING REALTY

MLS# A4537131 - Status: Active View Property Details Add to Favorites View Map

  • 617 SIESTA DR
  • Price: $1,850,000
  • Zip Code: 34242
  • 2709 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 5 Baths: 4
  • SIESTA KEY LIVING!!! Welcome home to your island getaway situated in the number one beach in the nation! A short five minute walk will have you dipping your toes in private shell beach or a five minute drive will see you right in the center of the vi ... Read More
  • Listing courtesy of: MODERN INTERNATIONAL REALTY, L