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# A4402294 - Status: Active View Property Details Add to Favorites View Map

  • 808 FREELING DR
  • Price: $2,499,900
  • Zip Code: 34242
  • 4852 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 3 Baths: 3+
  • Popular among boaters and water enthusiasts, this Bay Island Shores location on Siesta Key offers 100' of waterfront property on Roberts Bay. A distinctive home with an impressive great room perfect for entertaining, enhanced by the bay vistas and co ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4418207 - Status: Active View Property Details Add to Favorites View Map

  • 862 FREELING DR
  • Price: $2,200,000
  • Zip Code: 34242
  • 3002 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 4 Baths: 3+
  • Enjoy spectacular southern views of Roberts Bay and the intracoastal waterway from this home located on Bay Island on the northern tip of Siesta Key. This 2-story home has 4 bedrooms with 2nd floor balcony, 3.5 baths, wine bar/wet bar, 2-car garage, ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4422130 - Status: Active View Property Details Add to Favorites View Map

  • 3640 FLAMINGO AVE
  • Price: $1,790,000
  • Zip Code: 34242
  • 2984 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 3 Baths: 3+
  • Absolutely fabulous deepwater property with the best location on ever- popular, convenient Bay Island. On the most Northern end of Siesta Key, only minutes to Sarasota and #1 Siesta Beach, this property is one of the best values on the market today. ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4424349 - Status: Active View Property Details Add to Favorites View Map

  • 610 SIESTA DR
  • Price: $1,499,000
  • Zip Code: 34242
  • 1921 Square Feet
  • Subdivision: BAY ISLAND SHORES
  • Bedrooms: 3 Baths: 2+
  • Embracing the waterfront island lifestyle, this three-bedroom, one-level home is poised on deep sailboat water with easy access to the open waters of the Gulf. Located on north Siesta Key, arrive home to the oversized gated property where beautifully ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4431863 - Status: Active View Property Details Add to Favorites View Map

  • 3400 HAMILTON AVE
  • Price: $899,000
  • Zip Code: 34242
  • 3092 Square Feet
  • Subdivision: BAY ISLAND PARK
  • Bedrooms: 4 Baths: 3
  • Classic Key West-style residence on the north end of Siesta Key. Tucked away on Bay Island, between Sarasota's mainland and the north end of Siesta Key, the location can't be beat. Super close to Shell Beach, Bay Island Park, and a short distance to ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4408989 - Status: Active View Property Details Add to Favorites View Map

  • 3433 HAMILTON AVE
  • Price: $570,000
  • Zip Code: 34242
  • 1444 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 2 Baths: 2
  • Move right in and enjoy this wonderful pool home on Bay Island North Siesta Key. Large caged pool & spa. Screened area is 34'x43'. Very open and entertaining.4 sets of French doors go out to screened lanai for great access. Home is all tile floors, n ... Read More
  • Listing courtesy of: RE/MAX ALLIANCE GROUP