Bayside Homes with Gated Amenities

Welcome to Bayside, a picturesque subdivision nestled in the heart of Osprey, Florida. Known for its serene environment and luxurious living, Bayside offers an idyllic retreat for those seeking a perfect blend of comfort and sophistication. This charming community is situated in Sarasota County, just a stone's throw away from the stunning Gulf Coast beaches, making it an ideal location for beach lovers and outdoor enthusiasts alike.

Bayside is renowned for its beautifully designed homes, each exuding elegance and style. With a variety of architectural designs to choose from, prospective homeowners will find options that cater to their unique tastes and preferences. The community features gated amenities, ensuring residents enjoy a heightened sense of security and privacy. Imagine coming home to a tranquil oasis where you can unwind and relax, surrounded by lush landscaping and vibrant gardens.

In addition to the luxurious homes, Bayside offers a wealth of amenities that enhance the lifestyle of its residents. Spend your weekends lounging by the community pool, or take leisurely strolls along the scenic walking trails that wind through the neighborhood. The close-knit community vibe fosters a sense of belonging, where neighbors become friends and memories are made.

Situated conveniently near shopping, dining, and recreational activities, Bayside provides easy access to everything Osprey and Nokomis have to offer. Whether you’re looking to enjoy a day at the beach, savor fresh seafood at a local restaurant, or explore the vibrant arts scene, Bayside is the perfect place to call home. Experience the charm and elegance of Bayside—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 Gated Amenities

Newest Bayside Homes with Gated Amenities