Bayside Real Estate

Welcome to Bayside, an enchanting subdivision nestled in the heart of Osprey, Florida, just moments away from the stunning Nokomis coastline. This charming community offers a unique blend of serene living and vibrant coastal culture, making it an ideal place for families, retirees, and anyone in search of a tranquil lifestyle.

Bayside is renowned for its picturesque landscapes and well-maintained properties, where lush greenery meets the sparkling waters of the Gulf. With a variety of home styles, from modern single-family residences to cozy villas, there’s something to suit every taste and budget. Residents enjoy spacious lots that provide ample outdoor space for relaxation, gardening, or entertaining guests.

One of the highlights of living in Bayside is the sense of community. Neighbors become friends, fostering a warm and welcoming atmosphere. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational facilities, ensuring that everything you need is just a short drive away. For those who love the outdoors, nearby parks and nature reserves offer endless opportunities for hiking, biking, and enjoying Florida’s stunning sunsets.

Additionally, Bayside is just minutes from beautiful Nokomis Beach, where you can soak up the sun, swim in the crystal-clear waters, or take leisurely strolls along the shore. With its perfect blend of comfort, community, and coastal charm, Bayside is not just a place to live—it's a lifestyle waiting to be embraced. Come discover your dream home in this idyllic Florida haven!

$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 Real Estate

Newest Listings in Bayside