Oyster Bay Estates Homes with Boatable Water Water Frontage

Welcome to Oyster Bay Estates, a hidden gem nestled in the heart of South Sarasota, Florida. This picturesque subdivision is the ideal retreat for those seeking a serene lifestyle combined with the allure of waterfront living. With its tranquil surroundings and lush landscapes, Oyster Bay Estates offers an unparalleled blend of luxury and nature, making it a perfect choice for families, retirees, and anyone in between.

One of the standout features of this charming community is its access to boatable water, allowing residents to indulge in their love for boating, fishing, and water sports right from their backyards. Imagine stepping out of your beautifully designed home and onto your boat, ready to explore the stunning waterways and nearby Gulf Coast beaches. The homes in Oyster Bay Estates are thoughtfully designed, featuring spacious layouts, modern amenities, and breathtaking views that enhance the overall living experience.

The community is not just about homes; it's about a lifestyle. Residents can enjoy leisurely strolls along the scenic streets, gather with neighbors at community events, or simply unwind in the peaceful ambiance that surrounds them. With a prime location in South Sarasota, you’re just a short drive away from vibrant shopping, dining, and entertainment options, as well as the stunning beaches that make Florida famous.

Whether you're looking to create cherished family memories or seeking a peaceful haven to retire, Oyster Bay Estates offers a unique opportunity to enjoy the best of waterfront living in one of Florida's most desirable locations. Come discover the charm of Oyster Bay Estates, where your dream home awaits!

Newest Oyster Bay Estates Homes with Boatable Water Water Frontage

$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. Featuring 146 feet of pristine, direct frontage along the sparkling waters of Little Sarasota Bay, where sweeping panoramic views unfold, this walled and gated estate feels like a grand villa on the shores of Lake Como. A bold metallic gate, crowned with a striking Medusa head, sets the tone for the arrival experience, while two additional gold leafed gates - each equipped with electromagnetic openers - provide secure access, including a private entry to the neighboring yacht club. Encompassing more than 800 feet, the custom perimeter wall is more than a boundary: it’s a commanding architectural statement of luxury and artistry. Completely reimagined and expanded under the guidance of a classically trained Italian architect, the residence blends timeless European artistry with modern luxury. Inspired by Italy’s Villa del Balbianello and the iconic Casa Casuarina, the home showcases exquisite craftsmanship showcasing Venetian plaster walls, custom millwork gilded in 23-carat gold, hand-painted frescos, and pecky cypress ceilings. Spanning nearly 10,700 square feet of refined interiors, and over 4,000 square feet of air-conditioned space tailored for creativity and leisure, the home includes gracious entertaining areas, four ensuite bedrooms, four full and two half baths, and dual Clive Christian inspired kitchens designed for both family living and large-scale entertaining. Marvel at frescoed ceilings, stone-inlaid courtyards, and tranquil terraces that redefine elegance. Outside, lovely layered terraces and lush gardens frame peaceful, unobstructed bay views. A private dock with boat and jet-ski lifts anchors the waterfront lifestyle, while a resort style pool clad in shimmering mosaic tile, an octagonal pavilion, and a beautifully crafted summer kitchen elevate the outdoor experience to true luxury resort living. The sunken poolside kitchen is a beloved family gathering space ideal for relaxed al fresco dining. A large propane grill rises smoothly from its concealed appliance lift, while 100 year old Chicago reclaimed brick flooring, herringbone-pattern ceiling, and a beautiful maple wood dining set, create a warm, inviting ambiance. Thoughtfully curated seating areas capture breathtaking views in every direction, perfectly paired with spectacular year-round sunsets. Dive into luxury with the pool decking that elevates the iconic design of the Versace Property. Large, smooth marble stones imported directly from Italy weave a tapestry of geometric patterns that echo classic mythology. These intricate mosaics, true to Versace's legendary style, envelop the pool and its surroundings with a bold, artistic flair. A delicate Medusa mosaic graces the walkway, seamlessly connecting the pool area to the dock. Every element, from the imported Italian roof tiles to hand cast balustrades and hand painted frescos to the bespoke lighting and hardware reflects a deep commitment to authenticity, artistry, and permanence. Perfectly private yet ideally located near The Field Club and just minutes from Sarasota’s cultural scene, fine dining, and Gulf beaches, Villa Meraviglia stands as a rare masterpiece of design and craftsmanship. A world apart—where Old World elegance meets idyllic coastal living and every detail is a Living Gallery of beauty and craft.

1310 S Lake Shore Drive, Sarasota

$6,495,000

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

Virtually Staged. Panoramic Sarasota Bay views, a gated West of Trail setting in Oyster Bay Estates and an exceptional boating lifestyle define this remarkable waterfront residence overlooking the downtown Sarasota skyline and open waters. Blending timeless architectural details with expansive entertaining spaces and resort-inspired living, the home presents a rare opportunity to experience one of Sarasota’s most sought-after waterfront addresses. Brand-new impact-rated windows and doors are scheduled for installation in August/September 2026, further enhancing the property’s long-term value and storm readiness. A grand arrival sets the tone with travertine stairs leading to stately double entry doors framed by an arched transom window. Inside, expansive living and dining spaces are highlighted by intricate coffered ceilings, artisanal millwork, wainscoting-lined hallways and walls of sliding glass doors designed to maximize natural light while showcasing breathtaking water views. A carved stone gas fireplace anchors the main living area, while seamless indoor-outdoor flow enhances the home’s elevated waterfront atmosphere. Designed for both entertaining and everyday living, the chef’s kitchen features an oversized center island with prep sink, granite countertops, custom wood cabinetry and premium Viking® appliances paired with a Sub-Zero® professional refrigerator. A walk-in pantry with custom organization and an adjoining butler’s pantry with beverage cooler, dishwasher drawers and glass-front cabinetry create exceptional functionality for hosting. Breakfast and casual dining spaces are positioned to capture spectacular waterfront and skyline views from nearly every angle. The great room is surrounded by windows framing Sarasota Bay, lush tropical scenery and the downtown Sarasota skyline, while multiple entertaining bars with beverage coolers, prep sinks, dishwasher drawers and granite countertops provide ideal gathering spaces for family and guests. The primary suite serves as a luxurious private retreat featuring windows overlooking the water, a custom sitting area and a spa-inspired bath with travertine finishes, dual vanities, jetted soaking tub, oversized walk-in shower and custom-designed walk-in closet. A dramatic wood staircase leads to four additional en-suite guest bedrooms, each with access to an enormous balcony showcasing stunning downtown and water views. A three-stop elevator provides convenient access throughout all levels of the residence. The ground-level bonus area seamlessly connects to the resort-style pool deck, creating exceptional flexibility for indoor-outdoor waterfront living. Above the garage, a private guest apartment with separate staircase access offers a living area, kitchenette, spacious bedroom, full bath and private balcony, ideal for extended guests or multigenerational living. Additional highlights include hardwood flooring, plantation shutters, crown molding, custom tray and coffered ceilings, a central vacuum system and extensive architectural detailing throughout. Located minutes from Siesta Key, Southside Village and vibrant downtown Sarasota, this extraordinary Sarasota waterfront estate offers a rare combination of luxury bayfront living, boating access, panoramic sunset views and timeless coastal elegance in one of Sarasota’s premier West of Trail neighborhoods.

1137 N Lake Shore Drive, Sarasota

Start Your Search