Oyster Bay Estates Homes with Lake Front Water Frontage

Welcome to Oyster Bay Estates, a hidden gem nestled in the heart of South Sarasota, Florida. This picturesque subdivision is renowned for its stunning lakefront properties, offering residents a serene lifestyle surrounded by nature's beauty. With the gentle lapping of water at your doorstep and breathtaking views of the tranquil lakes, Oyster Bay Estates is truly a paradise for those seeking a peaceful retreat.

Each home in this charming community is designed to maximize the stunning waterfront views, with many featuring expansive outdoor living spaces perfect for entertaining or simply soaking in the Florida sunshine. Imagine sipping your morning coffee while watching the sun rise over the shimmering waters, or hosting evening gatherings with friends and family as the sun sets in a blaze of color.

Oyster Bay Estates is not just about beautiful homes; it’s about a lifestyle. Residents enjoy access to a variety of outdoor activities, from kayaking and paddleboarding to fishing and picnicking along the scenic shores. The community is also conveniently located near some of Sarasota’s best amenities, including shopping, dining, and cultural attractions.

Whether you’re looking for a year-round residence or a seasonal getaway, Oyster Bay Estates offers a unique blend of tranquility and convenience. Embrace the laid-back Florida lifestyle and discover the perfect home where you can create lasting memories by the water. Come explore the magic of Oyster Bay Estates—your dream home awaits!

Newest Oyster Bay Estates Homes with Lake Front Water 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

Start Your Search