Oyster Bay Estates

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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# A4590476 - Status: Active View Property Details Add to Favorites View Map

  • 1329 N LAKE SHORE DR
  • Price: $11,975,000
  • Zip Code: 34231
  • 6515 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • Pre-Construction. To be built. Perfectly situated in Oyster Bay, one of Sarasota's most coveted West of Trail neighborhoods, this contemporary custom home will be on an acre of land with 148 feet of water frontage along the intracoastal waterway. Spa ... Read More
  • Listing courtesy of: EXP REALTY LLC

MLS# A4591716 View Property Details Add to Favorites View Map

  • 1136 N LAKE SHORE DR
  • Price: $11,650,000
  • Zip Code: 34231
  • 1.41 Acres
  • Discover the captivating essence of 1136 N Lake Shore Drive in Oyster Bay Estates--a coveted 1.41-acre sanctuary along the pristine waters of Sarasota Bay. This exceptional property is the essence of waterfront living with over 430 feet on the bay cr ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4591433 - Status: Active View Property Details Add to Favorites View Map

  • 1136 N LAKE SHORE DR
  • Price: $11,650,000
  • Zip Code: 34231
  • 10234 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 6+
  • Discover the captivating essence of 1136 N Lake Shore Drive in Oyster Bay Estates--a coveted 1.41-acre sanctuary along the pristine waters of Sarasota Bay. This exceptional property is the essence of waterfront living with over 430 feet on the bay cr ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4590855 - Status: Active View Property Details Add to Favorites View Map

  • 4410 CAMINO REAL
  • Price: $9,950,000
  • Zip Code: 34231
  • 4988 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 5+
  • Embrace tranquility and unparalleled luxury in this exquisite waterfront masterpiece, where breathtaking views and stylish surroundings await. Nestled amidst a lush oasis of tropical landscaping, this custom-built 2019 residence seamlessly blends ele ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4585703 - Status: Active View Property Details Add to Favorites View Map

  • 1137 N LAKE SHORE DR
  • Price: $8,950,000
  • Zip Code: 34231
  • 6462 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 6 Baths: 6+
  • This unique gated waterfront estate is situated on a private cul-de-sac in one of the most coveted neighborhoods in Sarasota, Oyster Bay. This home blends definitive architectural features and exquisite finishes that create a remarkable yet comfortab ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4582548 - Status: Active View Property Details Add to Favorites View Map

  • 4431 CAMINO REAL
  • Price: $5,000,000
  • Zip Code: 34231
  • 5000 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 6 Baths: 6+
  • Pre-Construction. To be built. Architecturally Significant Sarasota School Modern Style Custom Build! Looking for more square feet or a smaller foot print? You're in charge! New floor plans and renderings are available for this home site with water ... Read More
  • Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4588075 View Property Details Add to Favorites View Map

  • 1329 N LAKE SHORE DR
  • Price: $4,750,000
  • Zip Code: 34231
  • 0.99 Acres
  • Nestled in Sarasota's highly coveted West of Trail neighborhood, Oyster Bay, this one acre cleared waterfront lot presents a rare opportunity for an ideal location to build a waterfront home. With 148 feet of water frontage along the intracoastal wat ... Read More
  • Listing courtesy of: EXP REALTY LLC

MLS# A4593160 - Status: Active View Property Details Add to Favorites View Map

  • 1451 REBECCA LN
  • Price: $3,500,000
  • Zip Code: 34231
  • 4683 Square Feet
  • Subdivision: OYSTER BAY LANDINGS
  • Bedrooms: 4 Baths: 5
  • Discover the pinnacle of waterfront living within Sarasota's coveted Oyster Bay Landings, a haven for boating enthusiasts. Nestled in an exclusive gated community, this bespoke residence epitomizes luxury, boasting unparalleled architectural finesse ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4597699 - Status: Active View Property Details Add to Favorites View Map

  • 1801 FIELD RD
  • Price: $2,987,500
  • Zip Code: 34231
  • 2975 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 5+
  • Under Construction. Prepare to be impressed with artful expressions of design, beautifully tailored interiors and an open brightness filling the home and welcoming you to further explore the many subtle nuances and brilliant examples of excellence in ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4585802 - Status: Active View Property Details Add to Favorites View Map

  • 1615 S LAKE SHORE DR
  • Price: $2,499,000
  • Zip Code: 34231
  • 4329 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3+
  • Beautiful lake front home in Oyster Bay on over half an acre with mature oak trees and luscious vegetation. You enter this custom 4300 square foot contemporary home through a lush private courtyard. Your attention is immediately drawn to the soaring ... Read More
  • Listing courtesy of: SARASOTA TRUST REALTY COMPANY

MLS# A4590190 View Property Details Add to Favorites View Map

  • 1514 S LAKE SHORE DR
  • Price: $1,790,000
  • Zip Code: 34231
  • 0.34 Acres
  • Outstanding buildable lot in Oyster Bay with rear Southern Exposure. X flood zone but near Sarasota Bay. Quiet affluent neighborhood with welcoming neighbors and one block from the beautiful Yacht and Tennis club, The Field Club. No mandatory asso ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4579921 - Status: Active View Property Details Add to Favorites View Map

  • 1514 S LAKE SHORE DR
  • Price: $1,790,000
  • Zip Code: 34231
  • 2430 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3
  • One or more photo(s) has been virtually staged. Nestled on one-third of an acre in the picturesque West of Trail community of Oyster Bay Estates, this captivating one-of-a-kind home combines striking artisan and architectural details with elegant cha ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY