Oyster Bay Estates

Listings For SaleSold History and Market Report

Oyster Bay Estates Real Estate for Sale – Sarasota, Florida 34231

Oyster Bay Estates

Oyster Bay Estates is one of the earliest luxury waterfront real estate in Sarasota, Florida. A few of the residences in this community date back to the 1910s–1920s era during which the state increasingly became a haven for vacationing snowbirds. Most of the waterfront residences here are located at the subdivision’s North and South Lake Shore Drive. Picturesque water views are likewise afforded by a lagoon at the neighborhood’s Camino and Westwood Lanes. The residences here are single family homes with eclectic designs spanning the tastes of nearly a century of development in Sarasota that includes Spanish Mediterranean, Key West or ranch styles, and contemporary Sarasota School of Architecture themes.

Oyster Bay Estates

Mature trees and lush landscaping further boost the community’s stimulating waterfront environment afforded by the scenic Roberts Bay adjacent toward the north to the larger Sarasota Bay. The property’s bay front area is also part of the Intracoastal Waterway, enabling easy passage to southwest Florida areas offering water-based life and leisure activities. The home sites of Oyster Bay are relatively larger than typical Sarasota residential lots, thus enabling a wider range of lifestyle possibilities for the subdivision’s residents.

Listings of Sarasota waterfront real estate for sale often feature available properties in the community with residential lots measuring from about 15,000 square feet to almost 23,000 square feet. The price points of Oyster Bay Estates homes can start near the $700s for an off-waterfront residence built in 1962 in a one-fourth acre lot with a 2,500-square-foot house having two bedrooms and two full baths. A $2.5 million asking price can be quoted for an updated waterfront home constructed in 1959 with a floor plan measuring 5,810 square feet with five bedrooms, three full baths and two half baths.

Oyster Bay Estates

Besides the community’s park, Oyster Bay Estates residents are also privileged with being neighbors to the prestigious and historic Field Club offering a wide variety of membership privileges such as tennis, boating, and swimming. Located a short distance south of the community, this club is in the National Register of Historic Places in recognition of its being one of several Florida Gold Coast winter homes built during the 1910s and the 1920s.

Notably, the neighborhood has no CDD fee and is also close to the bus line. Schools near the community include Philippi Shores Elementary, Brookside Middle, and Riverview High. Oyster Bay Estates’ location west of the Tamiami Trail provides convenient access to other Sarasota developments such as the Southside Village shops, Southgate Mall, and the gourmet market at the trendy Hyde Park area. As easily accessible are the Gulf Coast beaches, particularly those at the world famous Siesta Key only a few miles west of the Oyster Bay Estates. Downtown Sarasota and its centers for shopping, dining and arts and culture can also be reached within a few minutes from the community.


Oyster Bay Estates Real Estate for Sale

Below are all of the current real estate listings available for sale at Oyster Bay Estates.

Please contact us 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# A4414590 - Status: Active View Property Details Add to Favorites View Map

  • 1329 N LAKE SHORE DR
  • Price: $2,850,000
  • 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# 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# 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: $645,000
  • 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