Oyster Bay

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Oyster Bay Real Estate for Sale – Sarasota, Florida 34231

Oyster Bay Map

Oyster Bay Estates is one of Sarasota’s classic and historic waterfront neighborhoods steeped in history dating back to the 1910’s -20’s. Though many of the original homes have been torn down to make way for more modern estates, the neighborhood still retains much of that old Sarasota feel.

Lush tropical landscaping and primer waterfront estates make up the opulent atmosphere and charm found in this historic Sarasota development.

Many homes in this area are either canal-front or bay-side. Oyster Bay Estates is located on the mainland just south of the north Siesta Key Causeway, directly east of Siesta Key. Locals refer to Oyster Bay as being “West of The Trail” referring to the developments proximity to the west side of Tamiami Trail (US Highway 41). Highway 41 was named “Tamiami Trail” as it was the original highway heading south out of Tampa to Fort Meyers and then heading east to the city of Miami long before Interstate 75 replaced it as the main thoroughfare south to Miami.

Oyster Bay is central to the heart of Sarasota’s shopping opportunities, notable locations such as Southgate Mall, Southside Village shops and the gourmet market located in the trendy Hyde Park area are nearby.

The Field Club

One of Sarasota’s most venerable clubs is also located in the Oyster Bay area, The Field Club. The Field Club is one of the oldest astute establishments in Sarasota.

Originally the winter home of Stanley and Sara Carroll Brown Field, the club was originally one of several winter homes built on the “Gold Coast” of Florida during the 1910s and 1920s by the wealthy residents inhabiting the area. In 1957 the Fields offered the property to any club that would be interested in using it for club purposes for the minuscule sum if $175,000, unfortunately no Sarasota club at the time was interested in the property. It was a group of members of the Sarasota Yacht Club that purchased the property and agreed to the Fields terms and The Field Club was born. In 1986 The Field Club was listed in the National Register of Historic Places. Today, the Field Club’s members enjoy boating, tennis, swimming and a variety of activities that started with the vision of a winter resort home built by Stanley Field in 1925-27.

Oyster Bay features some of the finest old Florida real estate in Sarasota. This historic subdivision is ideally located close to all the best Sarasota has to offer which makes Oyster Bay real estate an attractive investment.


Oyster Bay Homes for Sale

Below you will find the current listings of homes and real estate currently for sale in Oyster Bay Estates.

Please contact me if you would like to schedule a tour of any of the listed properties.

MLS# A4520324 - Status: Active View Property Details Add to Favorites View Map

  • 1230 N LAKE SHORE DR
  • Price: $9,250,000
  • Zip Code: 34231
  • 4111 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • Are You A Discerning Buyer Who Prefers a Rare and Exclusive Waterfront Opportunity Unparalleled in Southwest Florida?...Welcome to This Exquisite New Offering on Roberts Bay in Sarasota's Prestigious Oyster Bay Estates...Refine the Existing Norman He ... Read More
  • Listing courtesy of: KELLER WILLIAMS ON THE WATER

MLS# A4519095 - Status: Active View Property Details Add to Favorites View Map

  • 1615 N LAKE SHORE DR
  • Price: $3,295,000
  • Zip Code: 34231
  • 3383 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 5+
  • Under Construction. Luxurious amenities define this fabulous new residence in Oyster Bay Estates that's been masterfully planned and executed with attention to detail that's second to none. The enticing "Kristi Ann Modern" plan is an artful creation ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4530983 - Status: Active View Property Details Add to Favorites View Map

  • 1525 N LAKE SHORE DR
  • Price: $3,080,000
  • Zip Code: 34231
  • 4407 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3+
  • Beautiful, custom home located in one of Sarasota's most sought-after West-of-the-Trail neighborhoods, Oyster Bay Estates. A Spanish-Italian designed home by custom-builder Bruce Saba. With over 4,400 sf of living space featuring a large great room ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY