Oyster Bay Estates Homes with Custom Architectural style

Oyster Bay Estates Homes with Custom Architectural style

Welcome to Oyster Bay Estates, a hidden gem nestled in the heart of South Sarasota, Florida. This picturesque subdivision is a haven for those seeking a tranquil lifestyle surrounded by nature's beauty. With its lush landscapes and serene waterways, Oyster Bay Estates offers a perfect blend of luxury and comfort, making it an ideal place to call home.

The homes in Oyster Bay Estates are a testament to exquisite craftsmanship and custom architectural styles that reflect the unique character of the community. Each residence is thoughtfully designed, showcasing stunning features and high-end finishes that cater to the most discerning tastes. From sprawling single-family homes to elegant waterfront properties, you’ll find a diverse selection of designs that truly stand out.

Living in Oyster Bay Estates means you’re just moments away from some of Sarasota’s best attractions. Enjoy a day at the nearby beaches, explore the vibrant arts scene, or indulge in world-class dining and shopping. The community is conveniently located near top-rated schools, parks, and recreational facilities, making it an excellent choice for families and professionals alike.

Nature lovers will appreciate the abundance of outdoor activities available in the area, from kayaking in the nearby bays to hiking the scenic trails in the surrounding parks. With its prime location and stunning homes, Oyster Bay Estates is more than just a neighborhood; it’s a lifestyle choice that offers the perfect balance of relaxation and adventure.

Discover the charm of Oyster Bay Estates today, and let us help you find your dream home in this idyllic community!

Newest Oyster Bay Estates Homes with Custom Architectural style

1136 N Lake Shore Drive, Sarasota
$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

1511 N Lake Shore Drive, Sarasota
$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

1804 N Lake Shore Drive, Sarasota
$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

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