Bayside Homes with Sidewalks Community Features

Welcome to Bayside, a charming subdivision nestled in the heart of Osprey/Nokomis, Florida, where coastal living meets suburban tranquility. This picturesque community in Sarasota County offers an idyllic setting for families and individuals alike, with homes designed to foster a vibrant and connected lifestyle.

Bayside is renowned for its beautifully landscaped streets lined with sidewalks, encouraging residents to enjoy leisurely strolls or invigorating morning jogs. The community's thoughtful design promotes an active lifestyle, making it easy to connect with neighbors and explore the scenic surroundings. Picture yourself walking your dog, riding bikes with the kids, or simply enjoying a peaceful evening stroll as the sun sets over the horizon.

The homes in Bayside are a perfect blend of modern elegance and coastal charm, featuring spacious layouts and contemporary finishes. Many residences boast private yards, ideal for hosting gatherings or enjoying serene moments in nature. With a variety of floor plans available, there’s a perfect fit for everyone—from young professionals to growing families.

Beyond the beautiful homes, Bayside is conveniently located near stunning beaches, vibrant shopping districts, and top-rated schools, making it a desirable location for both relaxation and recreation. Residents can easily access the best that Florida has to offer, from boating and fishing in the nearby Gulf waters to enjoying the cultural richness of Sarasota.

Come discover the Bayside community, where every day feels like a vacation, and experience the warm, welcoming atmosphere that makes this subdivision a true gem in Osprey/Nokomis. Your dream home awaits!

$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 Sidewalks Community Features

Newest Bayside Homes with Sidewalks Community Features