Bayside Homes with Bay/Harbor Frontage

Welcome to Bayside, a picturesque subdivision nestled in the heart of Osprey and Nokomis, Florida, where the sun-kissed shores meet serene bay waters. This enchanting community is a hidden gem in Sarasota County, offering residents a unique blend of coastal living and suburban charm.

Bayside boasts an array of stunning homes, many of which feature exclusive bay and harbor frontage. Imagine waking up to panoramic views of shimmering waters and gentle sea breezes, with the tranquil sounds of nature as your morning soundtrack. These waterfront properties provide not only a beautiful backdrop but also a lifestyle that embraces outdoor activities like boating, fishing, and kayaking, making it a haven for water enthusiasts.

The architectural styles in Bayside vary, ensuring there’s something for everyone—from modern coastal designs to classic Floridian aesthetics. Each home is designed with comfort and elegance in mind, often featuring spacious layouts, luxurious finishes, and private outdoor spaces perfect for entertaining or simply enjoying the sunset.

Beyond the beauty of the homes, Bayside offers a strong sense of community. Residents enjoy access to nearby parks, nature trails, and pristine beaches, making it easy to embrace the Florida lifestyle. With its close proximity to local shops, dining options, and cultural attractions, Bayside is not just a place to live; it’s a place to thrive.

Whether you’re looking for a year-round residence or a seasonal retreat, Bayside invites you to experience the perfect blend of luxury and leisure in one of Florida’s most desirable locations. Come discover your dream home in this idyllic waterfront community!

$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 Bay/Harbor Frontage

Newest Bayside Homes with Bay/Harbor Frontage