Bayside | Luxury Gated Waterfront Community in Osprey, Florida

Bayside in Osprey, Florida, is an exclusive gated enclave featuring custom-built waterfront homes along the shores of Little Sarasota Bay. This intimate community offers unmatched privacy, elegant architecture, and direct water access, making it one of the most prestigious neighborhoods in Sarasota County. Designed for refined coastal living, Bayside is ideal for those seeking tranquility, luxury, and natural beauty—just minutes from top-rated beaches, marinas, and dining.

Custom Homes with Coastal-Inspired Designs

Homes in Bayside are meticulously crafted with upscale features, open floor plans, and expansive living areas ranging from approximately 2,400 to over 4,000 square feet. Residences are tailored for indoor-outdoor living, with large screened lanais, private pools, and covered patios that embrace the Florida lifestyle. Many homes include gourmet kitchens with custom cabinetry and high-end appliances, spa-inspired master suites, and energy-efficient construction. Select homes offer private docks and boat lifts, providing direct access to the bay and Gulf waters.

Waterfront Amenities & Natural Serenity

Bayside is designed to foster a peaceful, outdoor-oriented lifestyle. Residents enjoy access to a private park, shaded walking trails, and scenic boardwalks nestled among mature oak trees and coastal foliage. A kayak and paddleboard launch provides easy access to Little Sarasota Bay, making it perfect for water lovers and nature enthusiasts. The gated entrance ensures privacy and security, while the community's low density maintains a serene, uncrowded atmosphere.

Prime Location Near Beaches & Everyday Conveniences

Despite its quiet and secluded setting, Bayside offers excellent proximity to some of the area’s most desirable destinations. Residents are just minutes from Nokomis Beach and the beautiful shores of Casey Key, as well as The Legacy Trail for biking and walking. Nearby Oscar Scherer State Park offers even more outdoor recreation, while downtown Sarasota and Venice provide boutique shopping, fine dining, and vibrant cultural attractions. Grocery stores, medical centers, and local services are conveniently close, giving homeowners the perfect mix of privacy and accessibility.

Discover Bayside in Osprey

Bayside in Osprey, Florida, offers a rare opportunity to own a luxurious waterfront home in an exclusive gated community. With private docks, bay views, and resort-style living just minutes from the Gulf, Bayside is the ultimate destination for elegant coastal living. Explore available homes in Bayside with Hunt Brothers Realty and discover your dream waterfront residence today.