Oyster Bay Estates Homes with Bay/Harbor Frontage

Welcome to Oyster Bay Estates, a hidden gem nestled in the heart of South Sarasota, Florida. This picturesque subdivision offers an unparalleled lifestyle, where the serene beauty of nature meets luxurious waterfront living. With its stunning bay and harbor frontage, Oyster Bay Estates is a dream destination for those seeking both tranquility and adventure.

As you enter this exclusive neighborhood, you’ll be captivated by the lush landscapes and charming architecture that define each home. The properties here boast expansive views of the sparkling waters, allowing residents to enjoy breathtaking sunrises and sunsets from the comfort of their own backyards. Imagine waking up to the gentle sound of waves lapping against the shore, or unwinding in the evening with a glass of wine while watching the boats glide by.

Oyster Bay Estates is not just about beautiful homes; it’s about a vibrant community. Residents enjoy a plethora of outdoor activities, from boating and fishing to kayaking and paddleboarding. The nearby beaches, parks, and nature trails provide endless opportunities for exploration and relaxation. Additionally, the subdivision is conveniently located near fine dining, shopping, and cultural attractions, ensuring that all your needs are just a stone’s throw away.

Whether you’re looking for a permanent residence or a seasonal retreat, Oyster Bay Estates offers an idyllic setting that embodies the essence of Florida living. Experience the charm and elegance of this remarkable community, where your waterfront dreams can become a reality. Come and discover why Oyster Bay Estates is the perfect place to call home!

Newest Oyster Bay Estates Homes with Bay/Harbor 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

Welcome to Villa Meraviglia — A Home Beyond Imagination. An extraordinary Neo-Classical Italian Renaissance estate set on 1.22 bayfront acres in Sarasota's exclusive Oyster Bay Estates. With 146 feet of direct frontage along the sparkling waters of Little Sarasota Bay and panoramic water views, this remarkable walled and gated property is both an architectural living gallery and a warm, inviting home designed to be lived in, enjoyed, and shared. Completely reimagined and expanded under the guidance of a classically trained Italian architect, the residence draws inspiration from Italy's Villa del Balbianello and the iconic Casa Casuarina. A bold metallic gate crowned with a striking Medusa head introduces the arrival experience, while two additional gold-leafed gates provide secure access, including a private entry to the neighboring yacht club. More than 800 feet of custom perimeter wall creates a dramatic architectural statement and exceptional privacy. Spanning nearly 10,700 square feet of refined interiors, plus more than 4,000 square feet of additional air-conditioned space for creativity and leisure, the home offers gracious yet comfortable spaces for everyday living and entertaining. Four ensuite bedrooms, four full and two half baths, and dual Clive Christian-inspired kitchens accommodate everything from intimate family meals to larger gatherings. Venetian plaster walls, 23-carat gold-gilded millwork, hand-painted frescoes, pecky cypress ceilings, stone-inlaid courtyards, and imported Italian materials reflect exceptional craftsmanship throughout. The waterfront lifestyle is equally compelling. Layered terraces and lush gardens frame peaceful bay views and create inviting places to gather, relax, dine, and enjoy spectacular year-round sunsets. A private dock with boat and jet-ski lifts makes boating and water sports part of everyday life. The resort-style pool, octagonal pavilion, and beautifully crafted summer kitchen create an exceptional outdoor gathering space. The sunken poolside kitchen, featuring a concealed appliance lift, 100-year-old reclaimed Chicago brick flooring, a herringbone-pattern ceiling, and maple dining table, is a warm and welcoming setting for relaxed alfresco meals and time with family and friends. Intimate seating areas throughout the property offer beautiful views in every direction. The pool deck is itself a work of art, with marble imported from Italy forming dramatic geometric patterns inspired by classic mythology. Intricate mosaics surround the pool, while a Medusa mosaic walkway connects the pool area to the dock. Perfectly private yet ideally located near The Field Club and just minutes from Sarasota's cultural scene, fine dining, and Gulf beaches, Villa Meraviglia offers a rare combination of architectural artistry and idyllic coastal living. A home of extraordinary artistry - yet equally designed for gathering, entertaining, enjoying the water, and experiencing the beauty of Sarasota Bay!

1310 S Lake Shore Drive, Sarasota

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