Bayside Homes with Bay/Harbor Frontage

Welcome to Bayside, a picturesque subdivision nestled in the heart of Osprey/Nokomis, Florida. This charming community offers a perfect blend of tranquility and coastal living, making it an ideal choice for those seeking a serene retreat while still being close to the vibrant culture of Sarasota County.

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 Coast. Imagine waking up to the gentle sounds of the waves and enjoying your morning coffee while watching the sun rise over the water. Each property is thoughtfully designed to maximize the natural beauty of the surroundings, with spacious layouts, lush landscaping, and outdoor living spaces perfect for entertaining or simply soaking in the serene atmosphere.

The community is not only about beautiful homes; it also offers a lifestyle enriched by nearby recreational opportunities. Residents can indulge in a variety of water activities, from boating and fishing to kayaking and paddleboarding. With the pristine beaches of Nokomis and Siesta Key just a short drive away, you’ll have endless opportunities for sun-soaked days and stunning sunsets.

Bayside is more than just a place to live; it’s a vibrant community where neighbors become friends and memories are made. Whether you’re looking for a permanent residence or a vacation getaway, Bayside in Osprey/Nokomis is the perfect destination to embrace the Florida lifestyle. Come explore the beauty and charm of Bayside, where 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 Bay/Harbor Frontage

Newest Bayside Homes with Bay/Harbor Frontage