Bayside Homes with Gated Amenities

Welcome to Bayside, a serene and picturesque subdivision nestled in the heart of Osprey, Florida, just a stone’s throw from the stunning Gulf Coast. This charming community offers a perfect blend of tranquility and convenience, making it an ideal haven for families, retirees, and anyone seeking a peaceful lifestyle without sacrificing access to vibrant local amenities.

Bayside is distinguished by its beautifully designed homes, each exuding a unique character while adhering to the community's high standards of architectural integrity. The homes feature spacious layouts, modern finishes, and lush landscaping, all contributing to the inviting ambiance of the neighborhood. Many properties in Bayside come equipped with gated amenities, providing an extra layer of security and peace of mind for residents. This gated environment fosters a sense of community, where neighbors can enjoy leisurely strolls, children can play freely, and everyone can relish the safety and serenity that this exclusive enclave offers.

Living in Bayside means you’re just minutes away from pristine beaches, world-class dining, and a plethora of outdoor recreational activities. Whether you’re exploring the nearby parks, indulging in local seafood, or soaking up the sun on the beach, Bayside serves as the perfect base for your Florida lifestyle.

Experience the charm and allure of Bayside—a community where your dream home awaits amidst the natural beauty and vibrant culture of Sarasota County. Come discover why so many have chosen to call this delightful neighborhood home!

$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