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# A4455314 - Status: Active View Property Details Add to Favorites View Map

  • 1441 REBECCA LN
  • Price: $4,650,000
  • Zip Code: 34231
  • 5889 Square Feet
  • Subdivision: OYSTER BAY LANDINGS
  • Bedrooms: 4 Baths: 4+
  • Inspired Coastal Design. Located in the private gated enclave of Oyster Bay Landings, this amazing waterfront residence combines unique architecture and incredible interior design to create a stunning yet comfortable and functional home. Set on a pro ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4442286 - Status: Active View Property Details Add to Favorites View Map

  • 1522 N LAKE SHORE DR
  • Price: $2,995,000
  • Zip Code: 34231
  • 4783 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • Tucked away on Lakeshore Drive in a storybook lakefront setting, this exquisite estate embodies tropical elegance and style. Luxurious appointments, state-of-the-art amenities, and a romantic water view present an artful backdrop for living. Beautifu ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4454495 - Status: Active View Property Details Add to Favorites View Map

  • 1818 N LAKE SHORE DR
  • Price: $2,449,000
  • Zip Code: 34231
  • 5968 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • Set in Oyster Bay Estates and remarkable in every way is Villa Lidia, a stunning example of architectural mastery and creatively imagined by acclaimed architect Thorning Little. Impressive in both indoor and outdoor living space as well as its classi ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4458536 - Status: Active View Property Details Add to Favorites View Map

  • 1207 N LAKE SHORE DR
  • Price: $2,350,000
  • Zip Code: 34231
  • 5043 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 5 Baths: 4+
  • This has to be one of the best waterfront opportunities in the marketplace today. Located on a boat basin in the beloved neighborhood of Oyster Bay, its setting is magical with a large backyard and private dock with lift. Serene views of the water ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4432539 - Status: Active View Property Details Add to Favorites

  • SARASOTA
  • Price: $1,995,000
  • Zip Code: 34231
  • 2582 Square Feet
  • Subdivision: OYSTER BAY LANDINGS
  • Bedrooms: 3 Baths: 3
  • This BAYFRONT cottage, West of Trail, in-town location of distinction seems worlds away yet enjoys easy accessibility to the very best Sarasota has to offer. Hidden behind the gates of OYSTER BAY LANDINGS is a winding tree-canopied brick lane that le ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4425835 - Status: Active View Property Details Add to Favorites

  • SARASOTA
  • Price: $1,460,000
  • Zip Code: 34231
  • 3657 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3+
  • Warm, Inviting and in a Stellar Location! Enter through the stunning, arched wood doorway, you will be met with a true sense of serenity. Every detail has been carefully thought of in this substantial Mediterranean Revival home. Grand columns accent ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4449196 - Status: Active View Property Details Add to Favorites View Map

  • 1613 FIELD RD
  • Price: $1,100,000
  • Zip Code: 34231
  • 3292 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3+
  • 1613 Field Rd. West of the trail in the sought-after Oyster Bay neighborhood. Featuring 3BR/3BA/2HBA, two story pool home with fully private fenced backyard. Perfect for entertaining family and friends. French doors in the living room overlook the ... Read More
  • Listing courtesy of: ASSOCIATES REALTY INC

MLS# A4424993 - Status: Active View Property Details Add to Favorites

  • SARASOTA
  • Price: $1,085,000
  • Zip Code: 34231
  • 2765 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 2+
  • Beautiful West of the Trail contemporary home in the sought-after Oyster Bay area and walking distance to The Field Club. It's situated on acre with beautiful gardens surrounding the home featuring exotic and lush tropical landscaping with a lap po ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4445171 View Property Details Add to Favorites View Map

  • 1630 N LAKESHORE DR
  • Price: $829,250
  • Zip Code: 34231
  • 0 Acres
  • West of Trail, Oyster Bay Estates, Spectacular Waterfront, Mature trees and landscaping, Riverview High School, The Field Club, and just minutes to Siesta Key, Publix, Sarasota Memorial Hospital, Selby Gardens, Downtown and more!For Existing home inf ... Read More
  • Listing courtesy of: PREFERRED COMMERCIAL INC

MLS# A4444434 - Status: Active View Property Details Add to Favorites View Map

  • 1630 N LAKESHORE DR
  • Price: $829,250
  • Zip Code: 34231
  • 2821 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3
  • Seldom available and a hidden gem West of the Trail and on the lake in Oyster Bay, one of the most sought out areas in Sarasota. The value of this property is in the land. The buyers wishing to create their own dream home the property offers unlimite ... Read More
  • Listing courtesy of: PREFERRED COMMERCIAL INC

MLS# A4455586 - Status: Active View Property Details Add to Favorites View Map

  • 1914 HILLSDALE PL
  • Price: $569,900
  • Zip Code: 34231
  • 1596 Square Feet
  • Subdivision: OYSTER BAY EAST
  • Bedrooms: 3 Baths: 2
  • ***OYSTER BAY EAST***LARGE LOT***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 in one of Sarasota ... Read More
  • Listing courtesy of: SUNCOAST PREMIER RLTY SOLUTION

MLS# A4451784 - Status: Active View Property Details Add to Favorites View Map

  • 1523 FIELD RD
  • Price: $525,000
  • Zip Code: 34231
  • 1549 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 2
  • This mid-century home in Oyster Bay Estates defines Florida living as it used to be. Lushly landscaped with oak trees, bamboo and exotic plants, you'll be living in a tropical wonderland. As you are welcomed in, you immediately feel the history and w ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY