Oyster Bay Estates Homes with Two Story Property Description

Welcome to Oyster Bay Estates, an enchanting subdivision nestled in the heart of South Sarasota, Florida. This picturesque community is the perfect blend of serene living and vibrant lifestyle, making it an ideal choice for families, retirees, and anyone looking to embrace the Florida sunshine.

Oyster Bay Estates boasts a collection of stunning two-story homes that are designed to cater to modern living while maintaining a sense of elegance. Each property features spacious layouts, allowing for an abundance of natural light to flow throughout the rooms. With well-appointed kitchens, expansive living areas, and luxurious master suites, these homes are perfect for entertaining guests or enjoying quiet family evenings.

The community is surrounded by lush landscapes and scenic waterways, providing residents with a tranquil environment to unwind and relax. Imagine sipping your morning coffee on a sun-drenched patio, or taking a leisurely stroll along the winding paths that meander through the neighborhood. Oyster Bay Estates is not just a place to live; it’s a lifestyle.

Conveniently located near some of Sarasota's finest amenities, residents have easy access to shopping, dining, and recreational activities. The beautiful beaches of Siesta Key and the vibrant arts district of downtown Sarasota are just a short drive away, offering endless opportunities for adventure and exploration.

In Oyster Bay Estates, you’ll find not just a house, but a true home where cherished memories are made. Discover the allure of this charming community and experience the best of South Sarasota living today!

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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