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# 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# 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# A4460954 - Status: Active View Property Details Add to Favorites View Map

  • 1313 S LAKE SHORE DR
  • Price: $2,300,000
  • Zip Code: 34231
  • 3003 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 3+
  • Mid-Century Modern, canal-front home on over 1/2 acre in desirable Oyster Bay Estates. Easy access to Roberts Bay/Intracoastal.Partial westerly views provide for breathtaking sunsets from the expansive backyard.Over 165' of concrete seawall with dock ... Read More
  • Listing courtesy of: HEMBREE AND ASSOC INC

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

  • 1207 N LAKE SHORE DR
  • Price: $2,250,000
  • Zip Code: 34231
  • 5043 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 5 Baths: 4+
  • The motivated owner has positioned this property 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 w/a large backyard and private dock wi ... 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: $2,250,000
  • 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# A4462797 - Status: Active View Property Details Add to Favorites View Map

  • 1430 KIMLIRA LN
  • Price: $1,700,000
  • Zip Code: 34231
  • 4460 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 5 Baths: 5
  • Stunning Oyster Bay 4460 sq.ft. estate has been carefully designed to blend into the natural setting of this secluded acre property. Beautifully imagined and masterfully constructed home features 5 bedrooms and 5 baths. A mix of hand scraped wood fl ... Read More
  • Listing courtesy of: THE RAY WILLIAMS GROUP LLC

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

  • 4439 WESTWOOD LN
  • 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# A4424993 - Status: Active View Property Details Add to Favorites View Map

  • 4487 CAMINO REAL
  • 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# A4449196 - Status: Active View Property Details Add to Favorites View Map

  • 1613 FIELD RD
  • Price: $999,000
  • 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# A4422136 View Property Details Add to Favorites View Map

  • 1511 S LAKE SHORE DR
  • Price: $995,000
  • 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# A4445171 View Property Details Add to Favorites View Map

  • 1630 N LAKESHORE DR
  • Price: $839,250
  • Zip Code: 34231
  • 0 Acres
  • Spectacular Lakefront Lot to build your dream home in coveted Oyster Bay Estates, one of the most sought after neighborhoods in Sarasota, Mature trees and landscaping, Riverview High School, The Field Club, and just minutes to Siesta Key, Publix, S ... Read More
  • Listing courtesy of: PREFERRED COMMERCIAL INC

MLS# A4464107 View Property Details Add to Favorites View Map

  • 1421 N LAKE SHORE DR
  • Price: $599,000
  • Zip Code: 34231
  • 0 Acres
  • Prime West of Trail single family home (buildable lot) located in the Oyster Bay Estates subdivision. Lot dimensions are 100' x 150' (.34 acre) Major renovation required to update this 1959 3BR/2BA wood frame home. Suggested best use is as teardown/d ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4464087 - Status: Active View Property Details Add to Favorites View Map

  • 1421 N LAKE SHORE DR
  • Price: $599,000
  • Zip Code: 34231
  • 2427 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 3 Baths: 2
  • Prime West of Trail single family home (buildable lot) located in the Oyster Bay Estates subdivision. Lot dimensions are 100' x 150' (.34 acre) Major renovation required to update this 1959 3BR/2BA wood frame home. Suggested best use is as teardown/d ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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: $515,000
  • 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