Oyster Bay Estates Homes with Two Story Property Description

Welcome to Oyster Bay Estates, a hidden gem nestled in the heart of South Sarasota, Florida. This charming subdivision offers a unique blend of tranquility and sophistication, making it the perfect place to call home. With its lush landscapes and serene waterways, Oyster Bay Estates is designed for those who appreciate the beauty of nature while enjoying modern amenities.

The homes in this picturesque community are predominantly two-story properties, each exuding elegance and style. These spacious residences boast open floor plans, allowing for seamless flow between living, dining, and entertaining spaces. Large windows invite an abundance of natural light, creating warm and inviting atmospheres throughout the day. Many homes feature stunning outdoor areas, perfect for hosting gatherings or simply enjoying the balmy Florida evenings.

Residents of Oyster Bay Estates enjoy a variety of amenities, including proximity to pristine beaches, world-class dining, and boutique shopping. The community is also conveniently located near top-rated schools and recreational facilities, making it an ideal choice for families. Whether you’re an outdoor enthusiast eager to explore nearby parks or someone who enjoys the vibrant arts scene that Sarasota has to offer, this neighborhood caters to all lifestyles.

In Oyster Bay Estates, you’re not just buying a home; you’re investing in a lifestyle. With its charming ambiance and welcoming community spirit, this subdivision is truly a place where dreams come to life. Discover your perfect two-story oasis in Oyster Bay Estates, where comfort meets luxury in the heart of South Sarasota. Come and experience the magic for yourself!

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

Start Your Search