Oyster Bay

Listings For SaleSold History and Market Report

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# A4582548 - Status: Active View Property Details Add to Favorites View Map

  • 4431 CAMINO REAL
  • Price: $5,000,000
  • Zip Code: 34231
  • 5000 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 5 Baths: 5
  • Pre-Construction. To be built. Welcome to 4431 Camino Real, an architectural masterpiece to be built in the upscale Oyster Bay Estates, Sarasota, Florida. This luxurious, lakefront property offers unparalleled elegance, boasting five spacious bedroom ... Read More
  • Listing courtesy of: KELLER WILLIAMS ON THE WATER S

MLS# A4574804 - Status: Active View Property Details Add to Favorites View Map

  • 1815 N LAKE SHORE DR
  • Price: $2,795,000
  • Zip Code: 34231
  • 3439 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3
  • Located "West of Trail" in one of the most sought-after areas in Sarasota this stunning home is perfectly positioned on a corner lot amidst the lush Florida landscape to deliver the utmost privacy yet be minutes from everything living in Sarasota has ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4579921 - Status: Active View Property Details Add to Favorites View Map

  • 1514 S LAKE SHORE DR
  • Price: $1,999,000
  • Zip Code: 34231
  • 2430 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3
  • Nestled on one-third of an acre in the picturesque West of Trail community of Oyster Bay Estates, this captivating one-of-a-kind home combines striking artisan and architectural details with elegant charm and comfort inside and out. The 2,430-SF resi ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY