Bayside Homes with Sidewalk Exterior features

Bayside Homes with Sidewalk Exterior features

Welcome to Bayside, a charming subdivision nestled in the heart of Osprey, Florida, just a stone's throw away from the picturesque Nokomis Beach. This vibrant community offers a perfect blend of tranquility and accessibility, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle in sunny Sarasota County.

Bayside is renowned for its beautifully designed homes, each featuring inviting sidewalks that encourage leisurely strolls and friendly neighborhood interactions. Imagine taking a morning walk along tree-lined streets, where neighbors greet each other with warm smiles and the scent of blooming flowers fills the air. These sidewalks not only enhance the aesthetic appeal of the community but also promote an active lifestyle, making it easy to enjoy the outdoors.

The homes in Bayside are thoughtfully crafted, showcasing a variety of architectural styles that cater to diverse tastes. With spacious layouts, modern amenities, and lush landscaping, these residences provide the perfect backdrop for creating lasting memories. Many homes also feature outdoor living spaces, ideal for entertaining guests or simply enjoying the beautiful Florida weather.

Beyond the charming homes and sidewalks, Bayside is conveniently located near top-rated schools, shopping centers, and recreational facilities. Residents can take advantage of nearby parks, golf courses, and the stunning Gulf Coast beaches, ensuring that there’s always something to do.

Discover the enchanting lifestyle that awaits you in Bayside, where community spirit meets natural beauty. Come explore your future home in this delightful subdivision today!

Newest Bayside Homes with Sidewalk Exterior features

$2,850,000
3 Beds 4 Baths A4684834 MLS
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/Nokomis

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