Oyster Bay Estates Homes with Intracoastal Waterway Frontage

Welcome to Oyster Bay Estates, a hidden gem nestled in the heart of South Sarasota, Florida. This exclusive subdivision offers a serene coastal lifestyle, where the Intracoastal Waterway serves as both a stunning backdrop and a gateway to adventure. With its prime location, Oyster Bay Estates is perfect for those seeking a tranquil retreat while still enjoying convenient access to the vibrant culture and amenities of Sarasota.

Homes in Oyster Bay Estates boast breathtaking waterway frontage, allowing residents to bask in the beauty of sunrises and sunsets over the shimmering waters. Each property is designed to maximize the stunning views, featuring spacious layouts, lush landscaping, and private docks for boating enthusiasts. Whether you’re an avid sailor or simply enjoy the peaceful ambiance of waterfront living, these homes provide the perfect setting for your dreams to unfold.

The community is characterized by its friendly atmosphere and a strong sense of belonging, making it an ideal place for families, retirees, and anyone seeking a welcoming neighborhood. Residents can enjoy leisurely strolls along the picturesque streets, take advantage of nearby parks, or indulge in the myriad of recreational activities that the Intracoastal Waterway offers, from kayaking to fishing.

With its prime location in South Sarasota, Oyster Bay Estates is also close to world-class dining, shopping, and cultural attractions, ensuring that you’re never far from the excitement. Experience the best of Florida living in Oyster Bay Estates, where luxury meets tranquility, and every day feels like a vacation. Come discover your dream home in this enchanting waterfront community!

Newest Oyster Bay Estates Homes with Intracoastal Waterway Frontage

$11,375,000

4 Beds ⋅ 8 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code

Some properties offer a view. This extraordinary 1.41 acre Oyster Bay estate offers an entire waterfront world of its own and is one of the best waterfront locations that Sarasota has to offer, with more than 430 feet along Sarasota Bay and a setting that feels virtually irreplaceable. Spanish and Mediterranean inspired architecture lends warmth, character, and timeless sophistication to this remarkable six bedroom residence, while its expansive shoreline creates a front row seat to spectacular sunsets, passing boats, and the natural beauty of Sarasota’s coastal landscape. With access to the Intracoastal Waterway and Gulf of Mexico, this is a rare opportunity for the luxury buyer who believes life is best lived on the water. Spanning more than 10,000 total square feet, with nearly all principal living areas on one level, the home was created for both grand entertaining and relaxed waterfront living. Dramatic ceilings, distinctive architectural details, expansive windows, and a spectacular gallery space with an interior fountain establish a sense of occasion, while multiple intimate gathering areas make the estate equally comfortable for everyday life. A commercial grade chef’s kitchen with professional appliances is equipped for effortless entertaining, from elegant dinners to large celebrations. The primary suite is a private sanctuary framed by beautiful bay views, featuring an expansive custom wardrobe and an indulgent bath with soaking tub, oversized shower, and dedicated massage and sauna room. Five additional bedroom suites provide exceptional privacy for family and guests, each with its own bath and generous storage. Beyond the interiors, the estate unfolds like a private resort. A swimming pool, tennis court, fitness room, billiard room, private office, three car garage, abundant storage, and permitted dock replacement create a property designed for recreation, relaxation, and life on the water. A new roof completed in 2024 adds further value and peace of mind. The address is equally exceptional. Oyster Bay Estates places you near The Field Club, Siesta Key, Southside Village, Sarasota Memorial Hospital, and Downtown Sarasota, offering remarkable access to world class beaches, boating, fine dining, shopping, arts, and culture while remaining tucked within a prestigious waterfront enclave. For those with an even greater vision, the magnificent acreage and extraordinary bay frontage also present the opportunity to create a completely new custom waterfront estate. The property may offer potential for division into two buildable homesites if the existing residence is removed, subject to verification and applicable approvals. With its commanding Sarasota Bay frontage, boating access, acreage, privacy, and coveted location, 1136 N Lake Shore Drive is not simply a place to live. It is the opportunity to claim an extraordinary piece of Sarasota’s waterfront lifestyle.

1136 N Lake Shore Drive, Sarasota

$26,400,000

4 Beds ⋅ 6 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code

Villa Meraviglia is a rare waterfront estate where architectural distinction and modern comfort come together in a home designed for an exceptional way of life. Set on 1.22 bayfront acres in Oyster Bay Estates, the residence commands 146 feet of direct frontage along the shimmering waters of Little Sarasota Bay. Here, mornings begin with light dancing across the water, afternoons unfold poolside, and evenings linger over dinner as the sun slips below the horizon. With panoramic western views and year-round sunsets, every day offers a front-row seat to the ever-changing beauty of the bay. Reimagined and completed in 2020, the estate draws inspiration from the worlds most famous waterfront villas. A striking custom gate creates a memorable sense of arrival, while two additional gold-leafed gates offer privacy and discreet access—including a private entrance to the neighboring yacht club. Inside, nearly 10,700 square feet of refined living space is complemented by more than 4,000 square feet of additional air-conditioned space devoted to leisure, entertainment, and creativity. Four beautifully appointed en-suite bedrooms offer private retreats, complemented by two stylish powder rooms for guests. Covered terraces extend from the main living areas on both levels to enjoy spectacular sunsets and sweeping bay views. The heart of the home is designed around gathering. With dual Clive Christian-inspired kitchens, every occasion, from a quiet breakfast to a celebratory dinner, unfolds with ease. Throughout the residence, Venetian plaster walls, 23-carat gold-gilded millwork, hand-painted frescoes, pecky cypress ceilings, stone-inlaid courtyards, and imported Italian materials create an atmosphere that feels timeless, distinctive, and deeply personal. Thoughtful luxuries extend throughout, from bespoke hardware, statement lighting and finishes to an elevator, whole-house generator and three-car garage. And then there are the spaces designed simply for enjoying life. Whether it is a family movie night, a spirited game of pool, or an evening gathered with friends, every space encourages connection. Outside, life naturally moves toward the water. Layered terraces create intimate settings for morning coffee, sunset cocktails, and quiet evenings beneath the stars. The resort-style pool becomes the center of days spent outdoors. The octagonal pavilion and beautifully crafted summer kitchen, with Chicago brick and a herringbone ceiling adding warmth and character, set the stage for effortless outdoor entertaining. The pool terrace is a destination in itself. Italian marble unfolds across the deck with intricate mosaics framing the water. A dramatic Medusa-inspired walkway draws you toward the private dock, where boat and jet-ski lifts make spontaneous days on the bay part of everyday life. From a morning cruise to a sunset ride across the water, the bay is always within reach. Here, luxury is something to experience. It is barefoot afternoons by the pool, dinners that stretch late into the evening, boats heading out at golden hour, and quiet mornings when the bay is perfectly still. Private and serene, yet close to The Field Club, Sarasota’s celebrated arts and dining scene, and the Gulf’s beautiful beaches, Villa Meraviglia offers a rare opportunity to live surrounded by beauty while remaining within easy reach of everything that makes Sarasota special. A remarkable home, an extraordinary setting, and a lifestyle meant to be savored.

1310 S Lake Shore Drive, Sarasota

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