Oyster Bay Estates, West of the Trail, Sarasota
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.
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# A3958259 View Property Details Add to Favorites View Map
- 1625 FIELD RD
- Price: $466,000
- Zip Code: 34231
- 2054 Square Feet
- Subdivision: OYSTER BAY ESTS
- Bedrooms: 3 Baths: 2+
- Most competively priced home in beautiful Oyster Bay Estates, West of the Trail. Large lot with custom 3 bedroom, 2.5 bath home. Open floor plan with sliders out to the pool. Vaulted ceilings in living room with fireplace. Wide open, light and bright ... Read More
- Listing courtesy of: MICHAEL SAUNDERS & COMPANY
MLS# A3937879 View Property Details Add to Favorites View Map
- 1460 REBECCA LN
- Price: $600,000
- Zip Code: 34231
- 0.301 Acres
- GATED, OYSTER BAY LANDINGS, a unique place to call home in the HEART OF SARASOTA W/BOAT DOCK. A private neighborhood created to be THE perfect place. Bricked dead end street with privacy all around you. A perfect setting for your new custom home. T ... Read More
- Listing courtesy of: PRUDENTIAL ELITE REAL ESTATE
MLS# A3937878 View Property Details Add to Favorites View Map
- 1450 REBECCA LN
- Price: $640,000
- Zip Code: 34231
- 0.3169 Acres
- GATED, OYSTER BAY LANDINGS, a unique place to call home in the HEART OF SARASOTA W/BOAT DOCK. A private neighborhood created to be THE perfect place. Bricked dead end street with privacy all around you. A perfect setting for your new custom home. Th ... Read More
- Listing courtesy of: PRUDENTIAL ELITE REAL ESTATE
MLS# A3953311 View Property Details Add to Favorites View Map
- 4577 CAMINO REAL
- Price: $799,000
- Zip Code: 34231
- 3841 Square Feet
- Subdivision: OYSTER BAY
- Bedrooms: 3 Baths: 3+
- Custom built by Bruce Saba and located in one of the most sought after neighborhoods in Sarasota, just south of the prestigious Field Club. A beautiful open floor plan with a large formal dining room and formal living room with soaring cathedral ceil ... Read More
- Listing courtesy of: MICHAEL SAUNDERS & COMPANY
MLS# A3959520 View Property Details Add to Favorites
- SARASOTA
- Price: $825,000
- Zip Code: 34231
- 3659 Square Feet
- Subdivision: OYSTER BAY ESTS
- Bedrooms: 4 Baths: 4
- AN OYSTER BAY TREASURE! THIS 1958 CUSTOM HOME HAS BEEN METICULOUSLY CARED FOR AND ADORED BY ONLY 2 FAMILIES SINCE IT WAS BUILT. SITUATED ON A LARGE LOT WITH WONDERFUL OAKS, FRUIT TREES, AND LANDSCAPING, THIS HOME OFFERS 4 BEDROOMS, 4 BATHROOMS, A LAR ... Read More
- Listing courtesy of: MICHAEL SAUNDERS & COMPANY
MLS# A3937874 View Property Details Add to Favorites View Map
- 1400 REBECCA LN
- Price: $1,400,000
- Zip Code: 34231
- 0.1712 Acres
- GATED/WATERFRONT, OYSTER BAY LANDINGS, a unique place to call home in the HEART OF SARASOTA W/BOAT DOCK. A private neighborhood created to be THE perfect place. Bricked dead end street with privacy all around you. A perfect setting for your new cust ... Read More
- Listing courtesy of: PRUDENTIAL ELITE REAL ESTATE
MLS# A3937873 View Property Details Add to Favorites View Map
- 1411 REBECCA LN
- Price: $1,600,000
- Zip Code: 34231
- 0.2406 Acres
- GATED/WATERFRONT, OYSTER BAY LANDINGS, a unique place to call home in the HEART OF SARASOTA W/BOAT DOCK. A private neighborhood created to be THE perfect place. Bricked dead end street with privacy all around you. A perfect setting for your new cust ... Read More
- Listing courtesy of: PRUDENTIAL ELITE REAL ESTATE
MLS# A3933350 View Property Details Add to Favorites View Map
- 1639 S LAKE SHORE DR
- Price: $1,680,000
- Zip Code: 34231
- 5915 Square Feet
- Subdivision: OYSTER BAY ESTS
- Bedrooms: 4 Baths: 4+
- Touched by Love--that is how to describe this recently built custom Tuscan style home in Oyster Bay, home of the prestigious Field Club.As you enter the foyer through the solid mahogany doors you are immediately captivated by the 22' ceilings and swe ... Read More
- Listing courtesy of: PREMIER SOTHEBY'S INTL. REALTY
MLS# A3949380 View Property Details Add to Favorites View Map
- 1324 S LAKE SHORE DR
- Price: $1,695,000
- Zip Code: 34231
- 5417 Square Feet
- Subdivision: OYSTER BAY ESTS
- Bedrooms: 4 Baths: 4+
- Welcome to one of Oyster Bay Estate's hidden treasures. Perfectly positioned on a cul-de-sac lot in one of Sarasota's most sought after communities, this newer Key West style home is both comfortable and sophisticated. The open floor plan includes f ... Read More
- Listing courtesy of: PREMIER SOTHEBY'S INTL. REALTY
MLS# A3948659 View Property Details Add to Favorites View Map
- 1607 S LAKE SHORE DR
- Price: $1,885,000
- Zip Code: 34231
- 6266 Square Feet
- Subdivision: OYSTER BAY ESTS
- Bedrooms: 5 Baths: 5+
- POND HOUSE- Exquisite gated lakefront estate - custom built, reflects charming Santa Barbara mission-style architecture - crafted with authentic elements specifically selected for this estate.Located minutes to downtown Sarasota (Theatres, Ballet, Re ... Read More
- Listing courtesy of: MICHAEL SAUNDERS & COMPANY
MLS# A3953984 View Property Details Add to Favorites View Map
- 1131 N LAKE SHORE DR
- Price: $2,450,000
- Zip Code: 34231
- 4570 Square Feet
- Subdivision: OYSTER BAY ESTS
- Bedrooms: 5 Baths: 5
- Entertain yourself with 170'of a beautiful panoramic bay view of the intracoastal waterway, rookeries, bridge and city lights in the prestigious Oyster Bay neighborhood. Dockage for large boats is just steps from yourback door and only a few short mi ... Read More
- Listing courtesy of: BEACHY PROPERTIES
MLS# A3955148 View Property Details Add to Favorites View Map
- 1249 N LAKE SHORE DR
- Price: $2,495,000
- Zip Code: 34231
- 5810 Square Feet
- Subdivision: OYSTER BAY ESTS
- Bedrooms: 4 Baths: 3+
- Oyster Bay is one of Sarasota's most prized communities, centered around the prestigious Field Club, once the private residence of the famed Marshall Field family. A Bay front community that is treasured by all who live there. This 5100 plus sq ft ho ... Read More
- Listing courtesy of: MICHAEL SAUNDERS & COMPANY
MLS# A3937881 View Property Details Add to Favorites View Map
- 1400 KENILWORTH ST
- Price: $2,800,000
- Zip Code: 34231
- 0.4336 Acres
- GATED/WATERFRONT, OYSTER BAY LANDINGS, a unique place to call home in the HEART OF SARASOTA W/BOAT DOCK. A private neighborhood created to be THE perfect place. Bricked dead end street with privacy all around you. A perfect setting for your new cust ... Read More
- Listing courtesy of: PRUDENTIAL ELITE REAL ESTATE
MLS# A3956954 View Property Details Add to Favorites View Map
- 1441 REBECCA LN
- Price: $3,975,000
- Zip Code: 34231
- 5871 Square Feet
- Subdivision: OYSTER BAY LANDINGS
- Bedrooms: 4 Baths: 4+
- Coastal Vintage Modern Masterpiece! Situated on a .42 acre lot, within the gates of a very private gated enclave in the coveted Field Club area, this beautifully detailed family residence presents as a new home. Rare attention to detail is seen from ... Read More
- Listing courtesy of: MICHAEL SAUNDERS & COMPANY
