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# A4201136 - Status: Active View Property Details Add to Favorites View Map

  • 4509 CAMINO REAL
  • Price: $2,295,000
  • Zip Code: 34231
  • 4400 Square Feet
  • Subdivision: OYSTER BAY
  • Bedrooms: 4 Baths: 3+
  • Built by Bruce Saba and designed by famed architect Guy Peterson, this four-bedroom designer home, "West of the Trail," is a private gem on about a 22,000SF lot, nestled among lush gardens, pavered walkways and a stunning courtyard. Enter the home th ... Read More
  • Listing courtesy of: Coldwell Banker Res R E

MLS# A4198495 - Status: Active View Property Details Add to Favorites View Map

  • 1615 S LAKE SHORE DR
  • Price: $2,250,000
  • Zip Code: 34231
  • 4642 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3+
  • Beautiful lake front address in Oyster Bay! Wooded setting with tall pines and old oaks on over an acre sets the scene for this custom-built home fronting onto a peaceful spring-fed lake where you are transported to the Carolinas. Contemporary styli ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4191233 View Property Details Add to Favorites View Map

  • 1400 KENILWORTH ST
  • Price: $2,250,000
  • Zip Code: 34231
  • 0 Acres
  • A rare opportunity to purchase a private peninsula in Oyster Bay Landings, a gated community West of Trail in Sarasota's exclusive Oyster Bay. Secluded, quiet and surrounded by water, this one-of-a-kind property is a haven of peace and relaxation. Th ... Read More
  • Listing courtesy of: Premier Sothebys Intl Realty

MLS# A4191231 - Status: Active View Property Details Add to Favorites View Map

  • 1400 KENILWORTH ST
  • Price: $2,250,000
  • Zip Code: 34231
  • 2582 Square Feet
  • Subdivision: OYSTER BAY LANDINGS
  • Bedrooms: 3 Baths: 3
  • This is a rare opportunity to live on a private peninsula in Oyster Bay Landings, a gated community West of Trail in Sarasota's exclusive Oyster Bay. Secluded, quiet and surrounded by water, this one-of-a-kind property is a haven of peace and relaxat ... Read More
  • Listing courtesy of: Premier Sothebys Intl Realty

MLS# A4193722 - Status: Active View Property Details Add to Favorites View Map

  • 4410 CAMINO REAL
  • Price: $1,949,000
  • Zip Code: 34231
  • 3018 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4
  • Spectacular and unique Oyster Bay Estates waterfront property. Well over a half acre on a private protected deep boat basin with wonderful Bay views and no fixed bridges. Only if desired, plans are included and ready for permitting on a Florida Coast ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4185525 - Status: Active View Property Details Add to Favorites View Map

  • 4487 CAMINO REAL
  • Price: $1,295,000
  • Zip Code: 34231
  • 2765 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 2+
  • West of Trail directly across from the Field Club, this stunning contemporary beautiful home in sought-after Oyster Bay. Situated on 1/2 acre with beautiful gardens surrounding the home featuring exotic and lush tropical landscaping with a lap pool w ... Read More
  • Listing courtesy of: Michael Saunders & Company

MLS# A4202274 - Status: Active View Property Details Add to Favorites View Map

  • 1610 S LAKE SHORE DR
  • Price: $1,250,000
  • Zip Code: 34231
  • 2821 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 2+
  • This charming West of the Trail updated home in Oyster Bay Estates with its southern exposure is one you must put at the top of your list! Entering the home, notice the beautifully refinished Bamboo flooring, the cathedral ceiling with whitewashed b ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E