Bayside Homes for Sale

Welcome to Bayside, a picturesque subdivision nestled in the charming coastal community of Osprey, Florida. Located in Sarasota County, Bayside offers a perfect blend of tranquility and convenience, making it an ideal destination for families, retirees, and anyone seeking a serene lifestyle by the water.

Bayside is renowned for its stunning natural beauty, featuring lush landscapes, mature trees, and a vibrant array of flora and fauna. Residents enjoy easy access to the shimmering waters of the Gulf of Mexico, with nearby beaches like Nokomis Beach and Siesta Key just a short drive away. The area is also home to a variety of parks, nature trails, and recreational opportunities, ensuring that outdoor enthusiasts will never run out of adventures to embark on.

The homes for sale in Bayside reflect the community's charm and appeal, with a diverse selection of architectural styles to suit any taste. From cozy single-family homes to spacious waterfront properties, each residence is designed with comfort and elegance in mind. Many homes feature modern amenities, open floor plans, and beautiful outdoor spaces perfect for entertaining or simply enjoying the stunning Florida sunsets.

In addition to its idyllic setting, Bayside boasts a welcoming community atmosphere, with friendly neighbors and a strong sense of belonging. Residents can take advantage of nearby shopping, dining, and cultural attractions, all while enjoying the laid-back lifestyle that this beautiful area has to offer.

Whether you're searching for your forever home or a seasonal retreat, Bayside in Osprey/Nokomis is a hidden gem waiting to be discovered. Come explore the homes for sale and find your piece of paradise in this enchanting subdivision!

$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 for Sale

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