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# A4162146 - Status: Active View Property Details Add to Favorites View Map

  • 3535 FLAMINGO AVE
  • Price: $3,099,000
  • Zip Code: 34242
  • 4103 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 4 Baths: 3+
  • Incredible North Siesta Key pool home with bay views and protected deep water boat basin. This home has over 4,100 sf of conditioned space and is perfectly situated on Bay Island, the gateway to world famous Siesta Key Beach. It is only minutes from ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4172756 - Status: Active View Property Details Add to Favorites View Map

  • 763 FREELING DR
  • Price: $1,995,000
  • Zip Code: 34242
  • 1616 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 3 Baths: 2
  • Location, location, location! * DEEP WATER! * PROTECTED HARBORAGE * Freeling Drive is known for its VERY DEEP SAILBOAT & YACHT BOATING WATER * 116 FEET ON ROBERTS BAY & 100 YARDS TO THE INTERCOASTAL WATERWAY & SARASOTA BAY, THEN ONTO THE GLORIOUS GUL ... Read More
  • Listing courtesy of: RE/MAX Alliance Group

MLS# A4190419 - Status: Active View Property Details Add to Favorites View Map

  • 830 SIESTA DR
  • Price: $1,750,000
  • Zip Code: 34242
  • 2499 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 3 Baths: 2
  • *******ONE OF THE FEW REMAINING BIG WATER VIEW BUILDING OPPORTUNITIES NEAR DOWNTOWN******* Breathtaking Roberts Bay VIEWS on SAILBOAT WATER with NEW SEAWALL and NEW DOCK. Highly sought after, North Siesta Key community BAY ISLAND SHORES. Minutes to ... Read More
  • Listing courtesy of: Key Solutions Real Estate Grp

MLS# A4188845 View Property Details Add to Favorites View Map

  • 830 SIESTA DR
  • Price: $1,750,000
  • Zip Code: 34242
  • 0 Acres
  • Breathtaking Roberts Bay VIEWS on SAILBOAT WATER with NEW SEAWALL and NEW DOCK. Highly sought after North Siesta Key community BAY ISLAND SHORES. Minutes to downtown Sarasota, Westfield Mall, fine dining, Siesta Key BEACH... Build new dream home, or ... Read More
  • Listing courtesy of: Key Solutions Real Estate Grp

MLS# A4187578 - Status: Active View Property Details Add to Favorites View Map

  • 779 SIESTA DR
  • Price: $769,000
  • Zip Code: 34242
  • 1888 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 3 Baths: 2
  • A most unique property located on Siesta Key - Bay Island. 3 bed 2 bath. Beautiful wood floors, fireplace, wrap around enclosed porches, large screened Lanai two storage buildings, fenced yard. Nestled in a beautiful private setting on a 15,000+ squa ... Read More
  • Listing courtesy of: ILENE MIRMAN REALTY INC

MLS# A4193152 - Status: Active View Property Details Add to Favorites View Map

  • 3446 ANGLIN DR
  • Price: $749,000
  • Zip Code: 34242
  • 1760 Square Feet
  • Subdivision: BAY ISLAND PARK
  • Bedrooms: 3 Baths: 2
  • Siesta Key Home! Stunning Bay Island on North Siesta Key. This 3 bedroom, 2 bath home flows beautifully with multilevel decks that overlook the nicely landscaped pool and garden area. The central living room is filled with natural light and opens o ... Read More
  • Listing courtesy of: Coldwell Banker Res R E

MLS# A4173415 - Status: Active View Property Details Add to Favorites View Map

  • 749 SIESTA DR
  • Price: $675,000
  • Zip Code: 34242
  • 2614 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 4 Baths: 2
  • Only minutes from the best beach in Florida ,Siesta Key Beach. Large fenced lot with lots of room for entertaining friends.lots of updates ... Read More
  • Listing courtesy of: JOHN YODER REALTY