Bayside Homes with Gated Amenities

Welcome to Bayside, a serene and picturesque subdivision nestled in the charming Osprey/Nokomis area of Sarasota County, Florida. This hidden gem is perfect for those seeking a tranquil lifestyle without sacrificing proximity to the vibrant culture and amenities of the Gulf Coast. With its lush landscapes and stunning waterfront views, Bayside offers an idyllic setting for families, retirees, and everyone in between.

One of the standout features of Bayside is its gated amenities, providing residents with an added layer of security and peace of mind. The gated entrance ensures that you can enjoy the serenity of your neighborhood while feeling safe and secure. As you explore Bayside, you’ll find beautifully designed homes that reflect a range of architectural styles, each thoughtfully crafted to complement the natural beauty of the surroundings.

Residents of Bayside have access to a wealth of amenities, including community parks, walking trails, and nearby beaches, making it easy to embrace an active, outdoor lifestyle. The subdivision is also conveniently located near shopping centers, fine dining, and cultural attractions, ensuring that everything you need is just a short drive away.

Whether you’re looking to unwind in your private oasis or engage with neighbors at community events, Bayside offers a welcoming atmosphere that fosters a true sense of belonging. Discover the charm of Bayside and find your dream home in this enchanting Florida community—where luxury meets nature, and every day feels like a vacation.

$2,850,000

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