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# A4405978 - Status: Active View Property Details Add to Favorites View Map

  • 1409 S LAKE SHORE DR
  • Price: $4,950,000
  • Zip Code: 34231
  • 5193 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3+
  • Pre-construction: TO BE BUILT. This incredibly beautiful home will be built on prestigious South Lake Shore Drive- a long-established, highly-regarded Oyster Bay Estates neighborhood. Tucked away on Sarasota's mainland, this private waterside oasis ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4414868 - Status: Active View Property Details Add to Favorites View Map

  • 1818 N LAKE SHORE DR
  • Price: $2,495,000
  • Zip Code: 34231
  • 5968 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 4+
  • This Oyster Bay Estates residence designed by accomplished architect, Thorning Little, embodies classic Italianate design with Moorish influences. Framed by mature palms and lush hedges, this West of the Trail home exudes Palm Beach garden glamour fu ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4414590 - Status: Active View Property Details Add to Favorites View Map

  • 1329 N LAKE SHORE DR
  • Price: $2,495,000
  • Zip Code: 34231
  • 3160 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 2+
  • Introducing this private 1-acre Old Florida style waterfront estate property in one of Sarasota's most beloved neighborhoods, Oyster Bay. This property enjoys 100 feet on the water and old Oaks and tropical flora serve as the backdrop for a charming ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4213972 - Status: Active View Property Details Add to Favorites View Map

  • 1235 N LAKE SHORE DR
  • Price: $2,395,000
  • Zip Code: 34231
  • 3535 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3
  • Water views in the front and back of this 4BR plus family and bonus rooms Oyster Bay home create an idyllic backdrop for an easygoing family lifestyle. This private residence is surrounded by lush manicured foliage, with a charming courtyard entry, p ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4404790 - Status: Active View Property Details Add to Favorites View Map

  • 1410 LADUE LN
  • Price: $1,150,000
  • Zip Code: 34231
  • 3570 Square Feet
  • Subdivision: OYSTER BAY / LADUE
  • Bedrooms: 4 Baths: 3+
  • LADUE LANE...Charming street in sought after location by the Field Club in the Oyster Bay area. Traditional family home with so many inviting spaces! The main house has 4 bedrooms, 3 baths, (3570 SF), the guest house above the garage has a large ope ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4419648 - Status: Active View Property Details Add to Favorites View Map

  • 1616 N LAKE SHORE DR
  • Price: $1,125,000
  • Zip Code: 34231
  • 2389 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3
  • Perfect west of the trail location to build your dream home. A true tropical haven, and one of the most sought after neighborhoods in Sarasota - Oyster Bay Estates abuts Sarasota Bay and is located next to the distinguished The Field Club; a private ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICE FLORIDA REALTY

MLS# A4215896 - Status: Active View Property Details Add to Favorites View Map

  • 4557 CAMINO REAL
  • Price: $995,000
  • Zip Code: 34231
  • 3771 Square Feet
  • Subdivision: OYSTER BAY
  • Bedrooms: 4 Baths: 4+
  • This charming four-bedroom Oyster Bay home is spacious and built with custom details. Located "West of the Trail" in a wonderfully central spot, only minutes from downtown Sarasota's bustling city life and unforgettable Gulf beaches at Siesta and Lid ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4417849 - Status: Active View Property Details Add to Favorites View Map

  • 1525 KENILWORTH ST
  • Price: $799,000
  • Zip Code: 34231
  • 2183 Square Feet
  • Subdivision: OYSTER BAY
  • Bedrooms: 3 Baths: 2
  • Stunning renovation west of the Trail! This light and bright California Contemporary has walls of windows and cathedral ceilings making it feel as one with the outdoors. The expansive floor plan features a separate dining room and huge great room flo ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4403669 - Status: Active View Property Details Add to Favorites View Map

  • 1906 HILLSDALE PL
  • Price: $630,000
  • Zip Code: 34231
  • 2126 Square Feet
  • Subdivision: OYSTER BAY EAST
  • Bedrooms: 3 Baths: 2+
  • Move in ready and casually elegant,updated home with stunning pool and outdoor living space situated on a quiet cul de sac. Renovated in 2012 with new roof, AC, sliding doors etc., built of high quality construction and former model home. An open an ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E