Oyster Bay Estates Homes with Pool View

Welcome to Oyster Bay Estates, a hidden gem nestled in the heart of South Sarasota, Florida. This picturesque subdivision offers a harmonious blend of serene living and vibrant community life, making it an ideal destination for families, retirees, and everyone in between. With its lush landscapes and charming streets, Oyster Bay Estates is not just a place to live; it’s a lifestyle.

One of the standout features of this delightful community is the stunning homes that boast breathtaking pool views. Imagine waking up every morning to the soothing sight of shimmering waters right in your backyard. Each residence is meticulously designed, offering spacious layouts and modern amenities that cater to your every need. Whether you’re hosting a summer barbecue by the pool or enjoying a quiet evening under the stars, these homes provide the perfect backdrop for both relaxation and entertainment.

Oyster Bay Estates is conveniently located near some of Sarasota's finest attractions. Enjoy easy access to pristine beaches, world-class dining, and vibrant shopping districts, all just a short drive away. For nature enthusiasts, the nearby parks and nature preserves offer endless opportunities for outdoor activities, from hiking to kayaking.

In Oyster Bay Estates, you don’t just find a home; you discover a community where neighbors become friends and every day feels like a vacation. With pool views that inspire tranquility and a location that provides the best of Florida living, this subdivision is truly a place where dreams come home. Come explore Oyster Bay Estates and find your slice of paradise today!

Newest Oyster Bay Estates Homes with Pool View

$2,095,000

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

Set on nearly half an acre in the heart of Oyster Bay Estates, this beautifully maintained and remodeled residence enjoys one of Sarasota's most sought-after addresses. Perfectly positioned West of the Trail, just minutes from Siesta Key, The Field Club, Southside Village, and downtown Sarasota, it offers an enviable location in the epicenter of Sarasota. Designed entirely on one level, the home spans more than 3,600 square feet with a floor plan that feels just as relevant today as when it was built. A welcoming entrance opens beneath soaring cathedral ceilings, while the living room, family room, kitchen, and outdoor spaces connect effortlessly, creating a natural flow throughout the home. Large sliding glass doors open to the pool and spa, creating a seamless connection between the home's interior living spaces and its treed outdoor entertaining areas. Privately positioned, the primary suite serves as a peaceful retreat with a spacious walk-in closet and an oversized bath. Three additional bedrooms provide comfortable accommodations for family and guests, with one thoughtfully incorporating a built-in office, offering flexibility for those who work from home. Zoned for highly regarded Phillippi Shores Elementary, the home is equally well suited for growing families as it is for those seeking the convenience of single-story living. The open kitchen has been updated with stone countertops and stainless appliances. Equally appealing are the features that provide everyday confidence. Situated in a preferred X flood zone, the home is equipped with a metal roof with enhanced hurricane tie-downs, impact-rated windows and doors, and a private irrigation well. Practical improvements add lasting value while making ownership that much easier. Perhaps its greatest strength is the flexibility it offers. Move in and enjoy it exactly as is or gradually make it your own over time. The location, the lot, and the floor plan provide an exceptional foundation, allowing the next owner to personalize the home without ever compromising what makes it so special.

1511 N 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

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