Bayside Homes with Bay/Harbor Frontage

Welcome to Bayside, an enchanting subdivision nestled in the picturesque landscape of Osprey and Nokomis, Florida. This serene community offers a unique blend of coastal charm and suburban tranquility, making it an ideal haven for those seeking a peaceful lifestyle while staying connected to the vibrant spirit of the Sunshine State.

Bayside is renowned for its stunning homes with bay and harbor frontage, providing residents with breathtaking views and easy access to the sparkling waters of the Gulf. Imagine waking up each morning to the gentle sounds of lapping waves and the sight of sun-kissed horizons right from your doorstep. These waterfront properties not only boast beautiful vistas but also offer a wealth of recreational opportunities, from boating and fishing to kayaking and paddleboarding—perfect for those who embrace an active, outdoor lifestyle.

The community is thoughtfully designed with lush landscaping, scenic walking trails, and inviting common areas that foster a sense of camaraderie among neighbors. Residents can enjoy leisurely strolls along the waterfront, gather for community events, or simply unwind while taking in the captivating sunsets that paint the sky in a kaleidoscope of colors.

Located just a stone's throw away from the cultural richness of Sarasota, Bayside residents have easy access to fine dining, boutique shopping, and world-class arts and entertainment. With its unique combination of natural beauty, luxurious waterfront living, and a vibrant local community, Bayside is more than just a place to live—it's a lifestyle waiting to be embraced. Come discover your dream home in this idyllic Florida paradise!

$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