Bay Island

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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# A4601040 - Status: Active View Property Details Add to Favorites View Map

  • 3799 FLAMINGO AVE
  • Price: $21,000,000
  • Zip Code: 34242
  • 8138 Square Feet
  • Subdivision: SIESTA KEY / BAY ISLAND
  • Bedrooms: 4 Baths: 4+
  • Discover your very own gated private peninsula on world-famous Siesta Key. Located on the north end of the island, this one-of-a-kind awe-inspiring furnished estate sits on more than an acre with over 700 waterfront feet. A custom-designed driveway l ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4579512 - Status: Active View Property Details Add to Favorites View Map

  • 684 FREELING DR
  • Price: $11,900,000
  • Zip Code: 34242
  • 2600 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 3 Baths: 3+
  • This amazing, READY TO BUILD waterfront lot just had a major price improvement. With 1.5 acres rarely found on Siesta Key, this ready to build lot is an estate parcel boasting nearly 350 feet of water frontage is a unique Siesta find. The completely ... Read More
  • Listing courtesy of: PREFERRED SHORE

MLS# A4586454 - 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+
  • This exceptional waterfront residence is located on a quiet side street on the coveted north end of Siesta Key. This house is just minutes from everything on and off the island. The house is perfectly positioned on a deep-water section of the intra-c ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4594471 - Status: Active View Property Details Add to Favorites View Map

  • 3532 FLAMINGO AVE
  • Price: $2,999,000
  • Zip Code: 34242
  • 3162 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 3 Baths: 3+
  • New price! Experience the pinnacle of island living on coveted Bay Island on north Siesta Key with this exceptional waterfront residence on deep sailboat water. Enjoy direct access to Sarasota Bay, Big Pass, and the Gulf of Mexico, and quick connecti ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4602754 - Status: Active View Property Details Add to Favorites View Map

  • 3458 ANGLIN DR
  • Price: $2,950,000
  • Zip Code: 34242
  • 2513 Square Feet
  • Subdivision: BAY ISLAND PARK
  • Bedrooms: 4 Baths: 2+
  • Welcome to Bay Island, the Gateway to Siesta Key! This beautiful home is the beginning of enjoying the Siesta Key lifestyle. The tropical landscaping of the property alone will make you feel like you are on vacation. The home sits on 2 lots -located ... Read More
  • Listing courtesy of: VETERANS REALTY INC.

MLS# A4584528 View Property Details Add to Favorites View Map

  • 546 FREELING DR
  • Price: $1,850,000
  • Zip Code: 34242
  • 0.27 Acres
  • Amazing New Build, Vacant Lot Opportunity on Bay Island, the premier location on the north end of Siesta Key, home of the America's #1 Beach!! Siesta Key is at the heart of Sarasota County and this ready-to-build waterfront lot offers quick access ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4572070 View Property Details Add to Favorites

  • SARASOTA
  • Price: $899,000
  • Zip Code: 34242
  • 0.39 Acres
  • Your own piece of Paradise, on the north end of Siesta Key, with easy access to all the wonderful amenities in the Village and the world class Crescent Beach. Additionally - close to Downtown Sarasota with exceptional dining, theatre, shopping and mo ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4562249 - Status: Active View Property Details Add to Favorites View Map

  • 831 SIESTA DR
  • Price: $899,000
  • Zip Code: 34242
  • 1202 Square Feet
  • Subdivision: BAY ISLAND
  • Bedrooms: 3 Baths: 2
  • Your own piece of Paradise, on the north end of Siesta Key, with easy access to all the wonderful amenities in the Village and the world class Crescent Beach. Additionally - close to Downtown Sarasota with exceptional dining, theatre, shopping and mo ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY