Oyster Bay Estates

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

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.

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.

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# A4591716 View Property Details Add to Favorites View Map

• 1136 N LAKE SHORE DR
• Price: $10,980,000
• 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: $10,980,000
• 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# A4637673 - Status: Active View Property Details Add to Favorites View Map

• 1521 S LAKE SHORE DR
• Price: $6,998,000
• Zip Code: 34231
• 4866 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 4 Baths: 5+
• Under Construction. The Windemere II is an extraordinary luxury custom home meticulously crafted by Heritage Builders. This coastal contemporary residence with clean lines is situated on a very rare West-of-Trail lakefront estate home site. The exqui ... Read More
• Listing courtesy of: HB REALTY GROUP INC.

MLS# A4641614 - Status: Active View Property Details Add to Favorites View Map

• 1137 N LAKE SHORE DR
• Price: $6,695,000
• Zip Code: 34231
• 6462 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 6 Baths: 6+
• Located West-of-Trail in one of Sarasota's sought-after neighborhoods, Oyster Bay Estates, this stunning waterfront home is designed for those who appreciate breathtaking views and effortless entertaining. With a prime position on Sarasota Bay, this ... Read More
• Listing courtesy of: PREMIER SOTHEBYS INTL REALTY

MLS# A4609533 - Status: Active View Property Details Add to Favorites View Map

• 1429 N LAKE SHORE DR
• Price: $5,995,000
• Zip Code: 34231
• 4545 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 5 Baths: 5+
• One or more photo(s) has been virtually staged. Under Construction. Welcome to a life of unparalleled luxury in an unrivaled location, where every detail has been meticulously crafted to create a haven of sophistication and comfort. Set within Oyster ... Read More
• Listing courtesy of: COLDWELL BANKER REALTY

MLS# A4638326 - Status: Active View Property Details Add to Favorites View Map

• 1804 N LAKE SHORE DR
• Price: $5,800,000
• Zip Code: 34231
• 6854 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 4 Baths: 4+
• Designed by esteemed architect John Potvin, this exceptional home combines elegance with casual tropical charm. Created with flexibility in mind, its three distinct structures--connected by covered lanais--provide privacy and grand spaces for sociali ... Read More
• Listing courtesy of: PREFERRED SHORE LLC

MLS# A4626321 - Status: Active View Property Details Add to Favorites View Map

• 4431 CAMINO REAL
• Price: $4,900,000
• Zip Code: 34231
• 3787 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 4 Baths: 4+
• Pre-Construction. To be built. Pre-Construction. To be built. Step into the pinnacle of modern luxury with this stunning home located in the prestigious Oyster Bay Estates built by The Holliday Group. Nestled on a generous 18,991 sq ft lot with 71 fe ... Read More
• Listing courtesy of: RE/MAX ALLIANCE GROUP

MLS# A4643558 - Status: Active View Property Details Add to Favorites View Map

• 1909 FIELD RD
• Price: $2,700,000
• Zip Code: 34231
• 2997 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 4 Baths: 3
• This exceptional custom-built residence with separate guest quarters is located in the highly sought-after Oyster Bay Estates on over half an acre of land and offers a private, luxurious lifestyle and a unique blend of modern upgrades. Situated in th ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4643968 - Status: Active View Property Details Add to Favorites View Map

• 1511 N LAKE SHORE DR
• Price: $2,699,000
• Zip Code: 34231
• 3613 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 4 Baths: 3+
• This Oyster Bay residence with well known address of "North Lakeshore Dr."....West of trail perfect location.....close to Siesta Key and the activities and also near the renowned "Field Club".The grand entrance is deserving of the compliments you wil ... Read More
• Listing courtesy of: MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC

MLS# A4643197 - Status: Active View Property Details Add to Favorites View Map

• 1610 S LAKE SHORE DR
• Price: $2,195,000
• Zip Code: 34231
• 2821 Square Feet
• Subdivision: OYSTER BAY ESTATES
• Bedrooms: 3 Baths: 2+
• Nestled among towering oaks and mature landscaping sits this mid-century modern home. On an oversized lot with a pavered circular driveway, a fully fenced yard that is perfect for pets, and a side entry oversized 2 car garage. This updated home exude ... Read More
• Listing courtesy of: MICHAEL SAUNDERS & COMPANY

MLS# A4645952 - Status: Active View Property Details Add to Favorites View Map

• 1434 LADUE LN
• Price: $2,125,000
• Zip Code: 34231
• 3466 Square Feet
• Subdivision: OYSTER BAY
• Bedrooms: 4 Baths: 3+
• Welcome to this beautifully updated 4-bedroom, 3.5-bathroom residence nestled in the highly sought-after Oyster Bay area. Perfectly positioned West of the Trail, outside of a flood zone, this charming residence offers the ideal blend of comfort, sty ... Read More
• Listing courtesy of: RE/MAX ALLIANCE GROUP