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# A4442286 - Status: Active View Property Details Add to Favorites View Map

  • 1522 N LAKE SHORE DR
  • Price: $3,100,000
  • 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# A4449050 - Status: Active View Property Details Add to Favorites View Map

  • 1818 LAKE SHORE DR
  • Price: $2,449,000
  • Zip Code: 34231
  • 5968 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 4+
  • This impeccably built custom home in one of the premier neighborhoods in Sarasota has everything you could want! With almost 6,000 square feet of refined living space, coupled with almost 2,000 feet of outdoor entertaining space it is fit for even t ... Read More
  • Listing courtesy of: KELLER WILLIAMS CLASSIC GROUP

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# A4443962 - Status: Active View Property Details Add to Favorites View Map

  • 1525 N LAKE SHORE DR
  • Price: $1,995,000
  • Zip Code: 34231
  • 4407 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3+
  • Spectacular Tuscan Masterpiece in Oyster Bay Estates, Sarasota's most coveted West-of-the-Trail neighborhood. This Spanish-Italian design home was built in 2006 by custom-builder Bruce Saba with impeccable finishes and the utmost attention to detail. ... Read More
  • Listing courtesy of: MICHAEL SAUNDERS & COMPANY

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

  • 1400 KENILWORTH ST
  • Price: $1,995,000
  • 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: $1,995,000
  • 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# 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# N6104544 - Status: Active View Property Details Add to Favorites View Map

  • 1511 N LAKE SHORE DR
  • Price: $1,374,900
  • Zip Code: 34231
  • 3613 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3+
  • Located in the coveted Oyster Bay neighborhood this Key West style exterior and contemporary interior home sits on a half acre lot. The newly remodeled open floor plan boasts 12 to 29 ft. ceilings and spacious well maintained rooms. The home offers f ... Read More
  • Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4439368 View Property Details Add to Favorites View Map

  • 1421 REBECCA LANE, LOT #3
  • Price: $1,200,000
  • Zip Code: 34231
  • 0 Acres
  • Oyster Bay Landings where your coastal dream home can come alive. Rare to find mainland, gated, and waterfront that is just off Roberts Bay near the coveted Field Club area. On protected boating water, this beautiful neighborhood features buried util ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4439369 View Property Details Add to Favorites View Map

  • 1431 REBECCA LANE, LOT #4
  • Price: $1,175,000
  • Zip Code: 34231
  • 0 Acres
  • Oyster Bay Landings where your coastal dream home can come alive. Tell your own story in this rare to find mainland, gated, and waterfront enclave just off Roberts Bay near the coveted Field Club area. On protected boating water, this beautiful neigh ... Read More
  • Listing courtesy of: GRECO REAL ESTATE

MLS# A4449196 - Status: Active View Property Details Add to Favorites View Map

  • 1613 FIELD RD
  • Price: $1,100,000
  • 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# A4431395 View Property Details Add to Favorites View Map

  • 1401 KENILWORTH ST
  • Price: $1,100,000
  • 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: $1,085,000
  • 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# 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# A4419652 View Property Details Add to Favorites View Map

  • 1616 N LAKE SHORE DR
  • Price: $965,000
  • 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: $965,000
  • 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# A4431400 View Property Details Add to Favorites View Map

  • 1405 KENILWORTH LOT 14 ST
  • Price: $950,000
  • 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# A4445171 View Property Details Add to Favorites View Map

  • 1630 N LAKESHORE DR
  • Price: $859,950
  • Zip Code: 34231
  • 0 Acres
  • West of Trail, Oyster Bay Estates, Spectacular Waterfront, Mature trees and landscaping, Riverview High School, The Field Club, and just minutes to Siesta Key, Publix, Sarasota Memorial Hospital, Selby Gardens, Downtown and more!For Existing home inf ... Read More
  • Listing courtesy of: PREFERRED COMMERCIAL INC

MLS# A4444434 - Status: Active View Property Details Add to Favorites View Map

  • 1630 N LAKESHORE DR
  • Price: $859,950
  • Zip Code: 34231
  • 2821 Square Feet
  • Subdivision: OYSTER BAY ESTATES
  • Bedrooms: 4 Baths: 3
  • Seldom available and a hidden gem West of the Trail and on the lake in Oyster Bay, one of the most sought out areas in Sarasota. The value of this property is in the land. The buyers wishing to create their own dream home the property offers unlimite ... Read More
  • Listing courtesy of: PREFERRED COMMERCIAL INC

MLS# A4451784 - Status: Active View Property Details Add to Favorites View Map

  • 1523 FIELD RD
  • Price: $525,000
  • 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