Bayside Homes with Gated Amenities

Welcome to Bayside, a hidden gem nestled in the heart of Osprey, Florida, where the sun-kissed shores meet serene living. This charming subdivision, located in Sarasota County, offers an idyllic blend of luxurious homes and a vibrant community atmosphere, making it the perfect place to call home.

Bayside is renowned for its stunning residences, each designed with elegance and comfort in mind. The homes here boast modern architectural styles, spacious layouts, and high-end finishes, ensuring that every family can find their dream home. Many properties feature lush landscaping, private pools, and outdoor living spaces ideal for entertaining or simply enjoying the beautiful Florida weather.

One of the standout features of Bayside is its exclusive gated amenities. Residents can enjoy peace of mind with secure access, allowing for a safe and tranquil environment. The community offers a wealth of recreational options, including walking trails, parks, and communal spaces that foster a sense of camaraderie among neighbors. Whether you're taking a leisurely stroll or hosting a weekend barbecue, Bayside provides the perfect backdrop for a vibrant lifestyle.

Located just minutes from the pristine beaches of Nokomis and the cultural attractions of Sarasota, Bayside allows residents to enjoy the best of both worlds. With easy access to shopping, dining, and entertainment, you’ll find everything you need right at your fingertips.

Discover the charm of Bayside, where luxury living meets a welcoming community. Come and experience the lifestyle you've always dreamed of!

$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