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# A4590476 - Status: Active View Property Details Add to Favorites View Map

  • 1329 N LAKE SHORE DR
  • Price: $11,975,000
  • Zip Code: 34231
  • 6515 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • Pre-Construction. To be built. Perfectly situated in Oyster Bay, one of Sarasota's most coveted West of Trail neighborhoods, this contemporary custom home will be on an acre of land with 148 feet of water frontage along the intracoastal waterway. Spa ... Read More
  • Listing courtesy of: EXP REALTY LLC

MLS# A4591716 View Property Details Add to Favorites View Map

  • 1136 N LAKE SHORE DR
  • Price: $11,650,000
  • Zip Code: 34231
  • 1.41 Acres
  • Discover the captivating essence of 1136 N Lake Shore Drive in Oyster Bay Estates--a coveted 1.41-acre sanctuary along the pristine waters of Sarasota Bay. This exceptional property is the essence of waterfront living with over 430 feet on the bay cr ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4591433 - Status: Active View Property Details Add to Favorites View Map

  • 1136 N LAKE SHORE DR
  • Price: $11,650,000
  • Zip Code: 34231
  • 10234 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 6+
  • Discover the captivating essence of 1136 N Lake Shore Drive in Oyster Bay Estates--a coveted 1.41-acre sanctuary along the pristine waters of Sarasota Bay. This exceptional property is the essence of waterfront living with over 430 feet on the bay cr ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4585703 - Status: Active View Property Details Add to Favorites View Map

  • 1137 N LAKE SHORE DR
  • Price: $8,950,000
  • Zip Code: 34231
  • 6462 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 6 Baths: 6+
  • This unique gated waterfront estate is situated on a private cul-de-sac in one of the most coveted neighborhoods in Sarasota, Oyster Bay. This home blends definitive architectural features and exquisite finishes that create a remarkable yet comfortab ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

  • 4431 CAMINO REAL
  • Price: $7,500,000
  • Zip Code: 34231
  • 5557 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 6 Baths: 6+
  • Pre-Construction. To be built. Welcome to the epitome of Sarasota luxury living at 4431 Camino Real--a prestigious, modern custom-built residence where elegance meets state-of-the-art living in the heart of Sarasota's exclusive Oyster Bay Estates. Th ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4607277 - Status: Active View Property Details Add to Favorites View Map

  • 1804 N LAKE SHORE DR
  • Price: $6,295,000
  • Zip Code: 34231
  • 6854 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • This unique home is designed to assemble your family and friends, to share good food, and to enjoy the good life. Esteemed architect John Potvin imagined three separate buildings connected by covered lanais to provide complete privacy when desired, b ... Read More
  • Listing courtesy of: PREFERRED SHORE

MLS# A4588075 View Property Details Add to Favorites View Map

  • 1329 N LAKE SHORE DR
  • Price: $4,750,000
  • Zip Code: 34231
  • 0.99 Acres
  • Nestled in Sarasota's highly coveted West of Trail neighborhood, Oyster Bay, this one acre cleared waterfront lot presents a rare opportunity for an ideal location to build a waterfront home. With 148 feet of water frontage along the intracoastal wat ... Read More
  • Listing courtesy of: EXP REALTY LLC

MLS# A4607865 - Status: Active View Property Details Add to Favorites View Map

  • 1525 N LAKE SHORE DR
  • Price: $3,590,000
  • Zip Code: 34231
  • 4407 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3+
  • This authentic old-world villa of stately proportions seems like it may have been plucked from the hills of Tuscany or Andalusia and planted in beautiful Oyster Bay Estates, Sarasota's treasured West of Trail community. Built with quality and luxury ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4593160 - Status: Active View Property Details Add to Favorites View Map

  • 1451 REBECCA LN
  • Price: $3,350,000
  • Zip Code: 34231
  • 4683 Square Feet
  • Subdivision: OYSTER BAY LANDINGS
  • Bedrooms: 4 Baths: 5
  • Discover the pinnacle of waterfront living within Sarasota's coveted Oyster Bay Landings, a haven for boating enthusiasts. Nestled in an exclusive gated community, this bespoke residence epitomizes luxury, boasting unparalleled architectural finesse ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4597699 - Status: Active View Property Details Add to Favorites View Map

  • 1801 FIELD RD
  • Price: $2,987,500
  • Zip Code: 34231
  • 3035 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 4+
  • Under Construction. Prepare to be impressed with artful expressions of design, beautifully tailored interiors and an open brightness filling the home and welcoming you to further explore the many subtle nuances and brilliant examples of excellence in ... Read More
  • Listing courtesy of: GRECO REAL ESTATE