Bayside Homes with Gated Amenities

Welcome to Bayside, a hidden gem nestled in the heart of Osprey and Nokomis, Florida. This enchanting subdivision is a perfect blend of serene living and modern conveniences, offering residents an idyllic lifestyle surrounded by nature’s beauty and the charm of coastal living.

Bayside is renowned for its exquisite homes, each thoughtfully designed to reflect the elegance and tranquility of the area. The community features a variety of architectural styles, ensuring there’s a perfect fit for every taste. With gated amenities, residents enjoy an added layer of privacy and security, making Bayside a coveted choice for families, retirees, and everyone in between.

As you explore this picturesque neighborhood, you'll find lush landscaping, scenic walking paths, and friendly neighbors who foster a strong sense of community. The gated entrance provides peace of mind, allowing you to relax and fully embrace the lifestyle that Bayside offers.

Beyond the gates, residents are just a stone’s throw away from the stunning beaches of Nokomis and the vibrant cultural scene of Sarasota. Enjoy the best of both worlds—tranquility at home and the excitement of nearby attractions, including fine dining, shopping, and outdoor activities.

Whether you're looking for a permanent residence or a vacation retreat, Bayside provides an exceptional living experience that combines luxury, comfort, and a welcoming community spirit. Discover the charm of Bayside and make it your new home in beautiful Sarasota County, Florida.

$2,995,000

3 Beds ⋅ 4 Baths ⋅ Bayside SubDv. ⋅ 34229 Zip Code

Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you upon entry, while the dramatic great room features a striking cupola with soaring 22-foot ceilings, wraparound windows, architectural beams, and detailed millwork that beautifully frame the waterfront setting. Pocketing impact sliders seamlessly open the living space to an expansive covered lanai where breathtaking sunsets, dolphins, and gentle coastal breezes create an unforgettable everyday backdrop. The open chef’s kitchen is designed for both entertaining and daily living, offering high end stainless appliances, a gas cooktop with pot filler, wine cooler, abundant cabinetry, and an oversized quartz island. Outdoor living shines with wood-paneled ceilings, crema pro leathered marble flooring, a gas fire pit, and a fully equipped outdoor kitchen with grill and beverage refrigerator. The solar and heat pump-heated saltwater lap pool and spa, outdoor shower, and private dock with lift complete the ultimate waterfront retreat. The primary suite enjoys beautiful water views and features a sitting area, double tray ceiling, dual custom walk-in closets, and a luxurious bath with double vanities and walk-in shower. Two additional en-suite bedrooms, a den or office, and a powder room provide comfort and flexibility. Wood-look tile flooring runs throughout, complemented by impact windows and doors, a smart-enabled security system, whole-home generator, and water conditioning system. Located just minutes from Casey Key, Nokomis Beach, Oscar Scherer State Park, and the Legacy Trail, this home offers effortless access to beaches, boating, dining, and recreation. An extraordinary waterfront residence where luxury, comfort, and coastal beauty come together, offering the lifestyle you’ve always imagined.

14401 Masthead Drive, Osprey

Bayside Homes with Gated Amenities

Newest Bayside Homes with Gated Amenities