Bayside Homes with Sidewalks Community Features

Welcome to Bayside, a vibrant and inviting subdivision nestled in the heart of Osprey, Florida, just minutes from the stunning Gulf Coast beaches. This charming community, located in Sarasota County, offers the perfect blend of serene suburban living with easy access to all the excitement and amenities that the Sunshine State has to offer.

Bayside is designed with families and active lifestyles in mind, featuring beautifully landscaped homes with sidewalks that encourage leisurely strolls and friendly neighborly interactions. Picture yourself taking evening walks along the tree-lined streets, where children can safely ride bikes and play, creating a warm and welcoming atmosphere that fosters community spirit.

The homes in Bayside are thoughtfully crafted, showcasing a variety of architectural styles that cater to diverse tastes. Whether you're looking for a cozy single-family home or a spacious abode for entertaining, you'll find options that fit your needs. Many residences boast modern amenities, open floor plans, and lush outdoor spaces, perfect for enjoying Florida's year-round sunshine.

Living in Bayside means you're just a stone's throw away from stunning beaches, parks, and recreational activities. Spend your weekends exploring the nearby Nokomis Beach or indulging in the vibrant local dining scene. With top-rated schools and convenient access to shopping and entertainment, Bayside stands as an ideal location for families, retirees, and anyone seeking a slice of paradise.

Discover the charm and community spirit of Bayside—where your dream home awaits!

$2,850,000

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 Sidewalks Community Features

Newest Bayside Homes with Sidewalks Community Features