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# A4424301 - Status: Active View Property Details Add to Favorites View Map

  • 1404 KENILWORTH ST
  • Price: $4,385,000
  • Zip Code: 34231
  • 5428 Square Feet
  • Subdivision: OYSTER BAY LANDINGS
  • Bedrooms: 4 Baths: 4+
  • Art you can live in! World renowned and acclaimed architect, Guy Peterson, designed another modern masterpiece of remarkable craftsmanship and pure minimalist aesthetic. It all began with a vision, an ambitious dream to imagine and design the consumm ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4428336 View Property Details Add to Favorites View Map

  • 1329 N LAKE SHORE DR
  • Price: $2,495,000
  • Zip Code: 34231
  • 0 Acres
  • 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# 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 with open views of Sarasota Bay 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 ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4436668 View Property Details Add to Favorites View Map

  • 1409 S LAKE SHORE DR
  • Price: $2,375,000
  • Zip Code: 34231
  • 0 Acres
  • Build your dream property on prominent South Lake Shore Drive- a long-established, highly-regarded Oyster Bay Estates neighborhood. Tucked away on Sarasota's mainland, this private waterside oasis spans almost an acre of beautifully treed landscape a ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

  • 1400 KENILWORTH ST
  • Price: $2,100,000
  • 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# A4432440 View Property Details Add to Favorites View Map

  • 1400 KENILWORTH ST
  • Price: $2,100,000
  • Zip Code: 34231
  • 0 Acres
  • This BAYFRONT, 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 leads thro ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

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

  • 1818 N LAKE SHORE DR
  • Price: $1,995,000
  • Zip Code: 34231
  • 5968 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • This property should be firmly on the radar of the savvy buyer seeking the utmost in quality construction with a classic Thorning Little architectural design. Delivering not only in value, scale and style, the home is located in one of the area's fin ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

  • 4439 WESTWOOD LN
  • Price: $1,650,000
  • 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# A4431395 View Property Details Add to Favorites View Map

  • 1401 KENILWORTH ST
  • Price: $1,200,000
  • Zip Code: 34231
  • 0 Acres
  • This 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 leads through a small secl ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

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

  • 4487 CAMINO REAL
  • Price: $1,170,000
  • 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# A4422136 View Property Details Add to Favorites View Map

  • 1511 S LAKE SHORE DR
  • Price: $1,100,000
  • Zip Code: 34231
  • 0 Acres
  • Located in one of the most sought-after neighborhoods in Sarasota, Oyster Bay Estates, this lake front lot features nearly 30,000 square feet of cleared, buildable land. The perfect site to build your dream home awaits you and includes a complete set ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4431400 View Property Details Add to Favorites View Map

  • Lot 14 KENILWORTH ST
  • Price: $1,000,000
  • Zip Code: 34231
  • 0 Acres
  • Tucked away in the exclusive West of Trail area of Sarasota, Oyster Bay Landings is a secluded waterfront enclave of 14 homesites. Bring your own builder to this waterfront property and make your dreams come alive! Level lot, set on protected boating ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4419652 View Property Details Add to Favorites View Map

  • 1616 N LAKE SHORE DR
  • Price: $985,000
  • Zip Code: 34231
  • 0 Acres
  • Nearly acre lake front lot in coveted Oyster Bay Estates! This is the perfect west of the trail location to build your dream home. Or, for those that love the mid-century style, work to revive this 1954 one story 2400 sq. ft. home. An updated survey ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

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

  • 1616 N LAKE SHORE DR
  • Price: $985,000
  • Zip Code: 34231
  • 2389 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3
  • Nearly acre lake front lot in coveted Oyster Bay Estates! This is the perfect west of the trail location to build your dream home. Or, for those that love the mid-century style, work to revive this 1954 one story 2400 sq. ft. home. An updated survey ... Read More
  • Listing courtesy of: BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

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

  • 1525 KENILWORTH ST
  • Price: $789,000
  • 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# A4430615 - Status: Active View Property Details Add to Favorites View Map

  • 1801 FIELD RD
  • Price: $479,000
  • Zip Code: 34231
  • 1682 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 2 Baths: 2
  • ** MUST SEE ** SELLER MOTIVATED, BRING AN OFFER ** Oyster Bay Estates Presents a Botanical Paradise in this Fantastic 2 Bed, 2 Bath Pool Home. Sitting on a 15,500ft2 (.35 acres) lot, native plantings, blooming flowers, soaring palms, plush grass and ... Read More
  • Listing courtesy of: SHIRLEY INTERNATIONAL REALTY