Bayside Homes for Sale

Welcome to Bayside, a hidden gem nestled in the heart of Osprey, Florida, where coastal charm meets modern living. This delightful subdivision, situated in Sarasota County, offers a unique blend of tranquility and convenience, making it the perfect place to call home. With its picturesque surroundings and close-knit community feel, Bayside is a haven for families, retirees, and everyone in between.

As you stroll through the tree-lined streets, you'll discover a variety of beautifully designed homes for sale that cater to diverse tastes and lifestyles. From spacious single-family residences to elegant townhomes, each property showcases the best of Florida living, with open floor plans, abundant natural light, and outdoor spaces perfect for entertaining or simply enjoying the serene environment. Many homes boast stunning views of the nearby waterways, allowing residents to indulge in the beauty of nature right from their backyards.

Beyond the homes, Bayside offers easy access to some of the most pristine beaches on the Gulf Coast, as well as a wealth of recreational opportunities. Whether you enjoy boating, fishing, or simply soaking up the sun, the nearby Nokomis Beach and the charming village of Osprey provide endless options for outdoor enthusiasts. Additionally, the area is home to a variety of shopping, dining, and cultural experiences, ensuring that you’ll never run out of things to do.

If you’re looking for a vibrant community with a relaxed atmosphere and a variety of homes for sale, Bayside in Osprey is the ideal choice. Come explore this enchanting neighborhood and discover the lifestyle you’ve always dreamed of!

$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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