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

  • 1818 N LAKE SHORE DR
  • Price: $2,249,000
  • 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# 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# 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: $1,150,000
  • 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

  • 0 KENILWORTH LOT 14 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: $775,000
  • 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# A4436235 View Property Details Add to Favorites View Map

  • 1555 EASTBROOK DR
  • Price: $749,000
  • Zip Code: 34231
  • 0 Acres
  • Begin your dream home West of the Trail. This charming four-bedroom pool home is situated on a corner lakefront parcel spanning nearly a quarter-acre of lush, manicured property. Waiting for you to renovate or begin a new build! Location in Sarasota ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E

MLS# A4432827 - Status: Active View Property Details Add to Favorites View Map

  • 1555 EASTBROOK DR
  • Price: $749,000
  • Zip Code: 34231
  • 1889 Square Feet
  • Subdivision: OYSTER BAY
  • Bedrooms: 4 Baths: 2
  • Begin your dream home West of the Trail. This charming four-bedroom pool home is situated on a corner parcel spanning nearly a quarter-acre of lush, manicured property. Waiting for you to renovate or begin a new build, the open layout offers tile flo ... Read More
  • Listing courtesy of: COLDWELL BANKER RES R E