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# A4493808 - Status: Active View Property Details Add to Favorites View Map

  • 1423 S LAKE SHORE DR
  • Price: $5,395,000
  • Zip Code: 34231
  • 6739 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 5 Baths: 5+
  • One or more photo(s) has been virtually staged. Spectacular one-of-a-kind location and privacy close to downtown Sarasota and minutes from the gorgeous award-winning Siesta Key beach. A truly custom-designed waterfront home built in 2016. 6,793 squar ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4495936 - Status: Active View Property Details Add to Favorites View Map

  • 4414 WESTWOOD LN
  • Price: $3,149,800
  • Zip Code: 34231
  • 4531 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • Pre-Construction. To be built. This expansive lakefront custom home is situated on an estate sized home site in Sarasota's coveted West of Trail area. Through a striking Entry Courtyard, Owners are greeted by a wide Great Room with expansive views of ... Read More
  • Listing courtesy of: HB REALTY GROUP INC.

MLS# A4487508 - Status: Active View Property Details Add to Favorites View Map

  • 1421 N LAKE SHORE DR
  • Price: $2,595,000
  • Zip Code: 34231
  • 4217 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • Under Construction. Currently under construction by renowned, award-winning Platinum Coast Construction with expected completion Summer 2021, this modern masterpiece has been planned with uncompromising detail, meticulous attention to architectural s ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4462797 - Status: Active View Property Details Add to Favorites View Map

  • 1430 KIMLIRA LN
  • Price: $1,675,000
  • Zip Code: 34231
  • 4460 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 5 Baths: 5
  • Stunning Oyster Bay 4460 sq.ft. estate has been carefully designed to blend into the natural setting of this secluded acre property. Beautifully imagined and masterfully constructed home features 5 bedrooms and 5 baths. A mix of hand scraped wood fl ... Read More
  • Listing courtesy of: THE RAY WILLIAMS GROUP LLC

MLS# A4495130 View Property Details Add to Favorites View Map

  • 1421 REBECCA LN
  • Price: $1,300,000
  • Zip Code: 34231
  • 0 Acres
  • Oyster Bay Landings one of the rarest neighborhoods in Sarasota. Waterfront, gated, private, on the mainland west of the trail, close to everything, and the Field Club is a short walk away. This particular lot is one of the last remaining lots in O ... Read More
  • Listing courtesy of: ROBERT MORRIS PROPERTIES LLC

MLS# A4495372 - Status: Active View Property Details Add to Favorites View Map

  • 1705 FIELD RD
  • Price: $798,600
  • Zip Code: 34231
  • 1985 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 2
  • RECENT $76,000 PRICE REDUCTION: Come live in this beautifully constructed contemporary home in very desirable Oyster Bay neighborhood just down the street from the historic Field Club on Sarasota Bay and a quick bike ride to the north bridge of Siest ... Read More
  • Listing courtesy of: PREFERRED SHORE

MLS# A4481101 - Status: Active View Property Details Add to Favorites View Map

  • 1914 HILLSDALE PL
  • Price: $569,950
  • Zip Code: 34231
  • 1596 Square Feet
  • Subdivision: OYSTER BAY EAST
  • Bedrooms: 3 Baths: 2
  • ***OYSTER BAY EAST***LARGE LOT***ROOM TO EXPAND***RECENT RENOVATIONS***CUL-DE-SAC LOT***LARGE POOL***SCREENED POOL/LANAI ENCLOSURE***IMMACULATE***MOVE IN READY*** Location, location, location...This recently renovated property the LOWEST PRICED HOME ... Read More
  • Listing courtesy of: SUNCOAST PREMIER RLTY SOLUTION