Oyster Bay Estates Homes with Two Story Property Description

Welcome to Oyster Bay Estates, a prestigious subdivision nestled in the heart of South Sarasota, FL. This exclusive community is located in Sarasota County and is renowned for its luxurious homes and serene surroundings.

Oyster Bay Estates is a hidden gem for those seeking a sophisticated and upscale lifestyle. The neighborhood boasts an array of stunning two-story properties that exude elegance and charm. From spacious floor plans to modern amenities, these homes are designed to offer both comfort and style.

Living in Oyster Bay Estates means enjoying the best of both worlds - a tranquil setting with easy access to all the conveniences of city life. Residents can take advantage of nearby shopping centers, top-rated schools, fine dining options, and pristine beaches just a short drive away.

Whether you're looking for a peaceful retreat or a place to entertain guests in style, Oyster Bay Estates has something for everyone. With its picturesque streets, lush landscaping, and upscale homes, this subdivision is truly a hidden paradise in South Sarasota.

Come and discover the beauty and elegance of Oyster Bay Estates, where luxury meets tranquility, and every day feels like a retreat. Experience the allure of two-story living in this exquisite neighborhood and make your dream home a reality in this coveted Sarasota community.

Newest Oyster Bay Estates Homes with Two Story Property Description

$4,995,000

4 Beds ⋅ 5 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code

A residence of sophistication and luxury, this exceptional home was thoughtfully designed to bring family and friends together—sharing good food, meaningful connection, and the enjoyment of elevated everyday living. Ideally located just 8 miles from Sarasota-Bradenton International Airport, 12 minutes to Siesta Key Beach, and 10 minutes to downtown Sarasota, the property is in close proximity to The Ringling, Van Wezel, Selby Gardens, Asolo, premier dining and shopping, The Field Club, and the Sarasota Yacht Club—creating a seamless blend of culture, convenience, and coastal lifestyle. Elegant yet warm and approachable, the home blends refined architecture with tropical elements, including stone columns, metal pergolas, concrete textures, and lush landscaping, creating a relaxed oasis unlike any other. A surrounding stucco wall enhances privacy, allowing you to unwind to the soothing sound of a tranquil fountain within a peaceful, secluded setting. The main living spaces were intentionally designed for gathering, featuring bead-board stained ceilings in the family room, formal living room, and dining area. The cook’s kitchen is both striking and highly functional, highlighted by a glazed pressed-tin ceiling, unpolished concrete floors, and views into the kitchen garden through multiple French doors and expansive windows—perfectly suited for both everyday living and entertaining.

1804 N Lake Shore Drive, Sarasota

$5,980,000

4 Beds ⋅ 7 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code

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 exquisite two-level residence redefines custom home living, flawlessly blending elegance, sophistication and comfort. As you step in the grand foyer, you are greeted by an expansive, open concept living space that seamlessly integrates the living, dining and kitchen areas. The gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, custom cabinetry and vast walk-in working pantry. This stunning home boasts four bedrooms, five luxurious baths and two convenient half baths. The primary suite, located on the first level overlooks the sparkling lake and features a designer bathroom private outdoor shower. For those who love to entertain, the Windemere II does not disappoint. Enjoy movie nights in the dedicated media room or host family gatherings in the versatile bonus room. A private study provides tranquil workspace. Ascend via the elegant custom staircase or convenient elevator to the upper level, where you will find two additional en-suite bedrooms, a large bonus room with wet bar and fitness room. Enjoy leisurely moments on the balcony overlooking the serene lake. Step through the massive pocketing sliding glass doors to discover your personal lakefront oasis – a breathtaking outdoor living retreat with a custom pool and spa and a fully equipped outdoor kitchen. Gather around the fire pit, perfect for cozy evenings under the stars. The Windemere II is not just a custom residence; it is a lifestyle. Experience the epitome of high-end-living and schedule a tour today! Floor plan located in attachments.

1521 S Lake Shore Drive, Sarasota

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