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

$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
$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
$4,695,000
4 Beds ⋅ 6 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
Perfectly positioned on a spacious, private lot in the prestigious and highly sought-after Oyster Bay Estates community, the residence embodies exceptional design, architectural intention, and refined livability. Custom designed and built by distinguished, award-winning Platinum Coast Construction and completed in 2021, this 4-bedroom / 4 full & 2 half bath modern masterpiece was crafted with uncompromising detail and a focus on seamless indoor–outdoor living. Inside, a host of elevated finishes creates a sophisticated yet welcoming atmosphere. Level 5 flat-smooth walls, engineered oak hardwood flooring, 8' solid-core and obscure glass interior doors, 10" baseboards, floating vanities in all baths, and Quartz surfaces throughout promote a clean, modern aesthetic. A dramatic 72" glass fireplace anchors the living area, while the gourmet kitchen boasts high-performance appliances including a Thermador push-to-open column refrigerator, column freezer, 24" wine preserver, Bosch dishwasher, Bosch combo oven/microwave, and 36” induction cooktop. The striking 175-bottle wine room with stone wall adds a stunning design focal point for entertainers and collectors alike. The primary suite offers a spa-like retreat with marble finishes, a Wetstyle soaking tub, and an enclosed outdoor garden area with tropical landscaping, wood decking, and a private outdoor shower. Guest suites each feature en-suite baths and access to a serene outdoor spa-like space with lush plantings, decking, and an outdoor tub and shower—creating peaceful, private escapes separate from the main living areas. Designed for true resort-style living, the exterior features a spectacular 18' x 30' pool and spa with a custom waterfall wall, surrounded by tropical landscaping. The fully equipped outdoor kitchen includes a 42” Blaze gas grill, under-counter refrigerator, outdoor sink, and storage drawers. Additional features include hurricane-impact windows, an advanced security system, irrigation system, and a distinctive 2-car garage with wood-look paneling and a stunning mahogany double-door entry with obscure glass. Situated just moments from Siesta Key, downtown Sarasota, and within walking distance of the prestigious Field Club, Oyster Bay Estates is celebrated for its beautiful streetscapes, active social atmosphere, and proximity to the water and premier amenities. This exceptional residence offers luxurious contemporary living in one of Sarasota’s most desirable neighborhoods.

1421 N Lake Shore Drive, Sarasota
$5,595,000
5 Beds ⋅ 7 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code
Virtually Staged. Experience luxury West-of-Trail living in Sarasota’s coveted Oyster Bay neighborhood. This newly built 2026 custom residence offers 5 bedrooms, 5 full and 2 half baths—all on one thoughtfully designed living level—featuring 4,545 sq. ft. under air and 5,689 sq. ft. total. Set on an impressive 130' x 150' corner lot (0.45 acres), the home is surrounded by a lush tropical oasis that provides exceptional privacy. A dramatic two-story foyer with 21’ ceilings and a steel-and-impact-glass entry door welcomes you inside. Engineered oak hardwood flooring, 10” baseboards, and sleek horizontal receptacles enhance the home’s modern architectural aesthetic. The expansive open-concept kitchen and great room are flooded with natural light from ten windows and four 20’ hurricane-impact glass sliders that open to the outdoor living space. The gourmet kitchen is a chef’s dream, offering an 8-seat center island, large walk-in pantry, quartz countertops, and premium appliances including a Bosch 36” natural gas/induction cooktop, 36” Thermador refrigerator column, 24” Thermador freezer column, 24” full-height Thermador wine cooler, Bosch dishwasher, and 30” Bosch oven/microwave combo. Retreat to the luxurious main suite featuring a Wetstyle tub with wood surround, marble accents, and slate and porcelain flooring. Additional highlights include level-5 smooth interior walls, 8’ solid-core and obscure-glass interior doors, a stunning 175-bottle wine room with marble wall and glass enclosure, Samsung pedestal washer & dryer, and an advanced alarm and exterior security lighting system. The outdoor living area is designed for year-round enjoyment with a summer kitchen equipped with a Blaze 42” gas grill, sink, and under-counter refrigerator. A 15’ x 28’ pool and spa with a custom waterfall feature, plus an outdoor shower, complete this private retreat. The property also offers an irrigation system and a spacious 3-car garage. An exceptional opportunity to own a brand-new, luxury single-level home in one of Sarasota’s most desirable West-of-Trail communities.

1429 N Lake Shore Drive, Sarasota
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