Oyster Bay Estates Homes with Lake Front Frontage

Welcome to Oyster Bay Estates, an enchanting enclave nestled in the heart of South Sarasota, Florida. This stunning subdivision offers a unique blend of tranquility and luxury, making it the perfect place to call home. Known for its picturesque landscapes and serene atmosphere, Oyster Bay Estates is a hidden gem that attracts those seeking a peaceful lifestyle amidst the vibrant charm of Sarasota.

One of the standout features of this exquisite community is its beautiful homes with lakefront frontage. Picture waking up each morning to breathtaking views of shimmering waters, where gentle ripples dance in the sunlight and the soothing sounds of nature provide a calming backdrop. These lakefront properties not only offer an idyllic setting for relaxation but also create a perfect ambiance for entertaining family and friends.

The architecture in Oyster Bay Estates is as diverse as its residents, with homes designed to embrace the beauty of their surroundings. From modern designs to classic Floridian styles, each residence showcases thoughtful craftsmanship and attention to detail. Many homes feature expansive outdoor living spaces, ideal for enjoying sunset views over the water or hosting memorable gatherings under the stars.

Beyond the boundaries of your dream home, the community offers easy access to South Sarasota’s vibrant cultural scene, pristine beaches, and lush parks. Whether you're exploring the nearby shops, indulging in local cuisine, or taking a leisurely stroll along the water's edge, Oyster Bay Estates provides a lifestyle that is both enriching and fulfilling.

Discover the magic of Oyster Bay Estates, where lakefront living meets the best of Florida’s coastal charm. Your dream home awaits!

Newest Oyster Bay Estates Homes with Lake Front Frontage

$5,980,000

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

The Windemere II is an extraordinary luxury custom home meticulously crafted by Heritage Builders. This coastal contemporary residence with clean lines is situated on a very rare West-of-Trail lakefront estate home site. The exquisite two-level residence redefines custom home living, flawlessly blending elegance, sophistication and comfort. As you step in the grand foyer, you are greeted by an expansive, open concept living space that seamlessly integrates the living, dining and kitchen areas. The gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, custom cabinetry and vast walk-in working pantry. This stunning home boasts four bedrooms, five luxurious baths and two convenient half baths. The primary suite, located on the first level overlooks the sparkling lake and features a designer bathroom private outdoor shower. For those who love to entertain, the Windemere II does not disappoint. Enjoy movie nights in the dedicated media room or host family gatherings in the versatile bonus room. A private study provides tranquil workspace. Ascend via the elegant custom staircase or convenient elevator to the upper level, where you will find two additional en-suite bedrooms, a large bonus room with wet bar and fitness room. Enjoy leisurely moments on the balcony overlooking the serene lake. Step through the massive pocketing sliding glass doors to discover your personal lakefront oasis – a breathtaking outdoor living retreat with a custom pool and spa and a fully equipped outdoor kitchen. Gather around the fire pit, perfect for cozy evenings under the stars. The Windemere II is not just a custom residence; it is a lifestyle. Experience the epitome of high-end-living and schedule a tour today! Floor plan located in attachments.

1521 S Lake Shore Drive, Sarasota

$4,400,000

4 Beds ⋅ 5 Baths ⋅ Oyster Bay Estates SubDv. ⋅ 34231 Zip Code

Move in Ready New Construction on Prime Lakefront Lot in exclusive Oyster Bay Estates. Welcome to modern luxury living, safely outside the flood zone and offering a refined alternative to barrier island life. This brand-new contemporary masterpiece combines striking architectural design with uncompromising quality construction. Built with solid block construction, impact windows, and dramatic 10-foot impact sliders throughout, this home delivers both beauty and peace of mind. Step inside through the beautiful Mahogany front door to soaring ceilings up to 21 feet and wide-plank French oak flooring that flows throughout the light-filled living spaces. The gourmet kitchen is a chef’s dream, featuring a Thermador Professional Series appliance package with a dual-fuel gas range, plus an oversized island perfect for entertaining and everyday gathering. The thoughtful split floor plan offers 4 bedrooms, 4.5 bathrooms, and a versatile den — ideal for privacy and flexible living. From the moment you walk in, the sparkling lake and resort-style pool take center stage, setting the tone for effortless Florida living. Enjoy alfresco dining and relaxing evenings in the covered outdoor kitchen and seating area overlooking the water. Additional highlights include an oversized 3-car side-load garage, full irrigation system, and a whole-house generator for added convenience and security. Energy-efficient features include Icynene spray foam insulation and a multi-zone HVAC system with advanced filtration — smart, sustainable comfort year-round. Ideally situated in a top-rated school district, this exceptional home offers the perfect blend of luxury, convenience, and safety. Close to the award winning beaches of Siesta Key without all the day to day traffic and also easy access to downtown. Come experience Sarasota living at its finest.

4431 Camino Real, Sarasota

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