Bayside Homes for Sale

Welcome to Bayside, a picturesque subdivision nestled in the heart of Osprey and Nokomis, Florida, where coastal charm meets contemporary living. This enchanting community is a hidden gem in Sarasota County, offering an idyllic lifestyle that combines tranquility with convenience.

Bayside is renowned for its lush landscapes, serene waterways, and close-knit community atmosphere. Residents enjoy easy access to stunning Gulf Coast beaches, including the nearby Nokomis Beach and the pristine sands of Siesta Key. Whether you’re looking to soak up the sun, enjoy water sports, or simply take a leisurely stroll along the shore, Bayside places you right in the heart of Florida’s natural beauty.

The homes for sale in Bayside are as diverse as the residents who call this community home. From charming single-family residences to modern townhomes, each property boasts unique architectural styles and thoughtful designs that cater to a variety of lifestyles. Many homes feature spacious layouts, gourmet kitchens, and private outdoor spaces perfect for entertaining or enjoying a quiet evening under the stars.

In addition to its stunning homes, Bayside offers residents a wealth of amenities. Enjoy nearby parks, walking trails, and community events that foster a sense of belonging and connection among neighbors. With local shops, dining options, and top-rated schools just a short drive away, Bayside truly embodies the perfect blend of leisure and convenience.

If you’re ready to embrace the Bayside lifestyle, explore our listings today and discover your dream home in this charming Florida community!

$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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