Oyster Bay Homes for Sale

Oyster Bay Homes for Sale

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida, within the beautiful Collier County. This charming subdivision is renowned for its stunning waterfront properties, lush landscapes, and an inviting community spirit that makes it a desirable destination for families, retirees, and anyone looking to embrace the Florida lifestyle.

Oyster Bay boasts a variety of homes for sale, each uniquely designed to capture the essence of coastal living. From luxurious waterfront estates with private docks to cozy single-family homes surrounded by serene gardens, there’s a perfect property for every taste and budget. Many homes feature expansive outdoor spaces, ideal for entertaining or simply enjoying the breathtaking sunsets that Naples is famous for. With modern amenities and thoughtful architectural details, these homes provide a comfortable and stylish living experience.

Residents of Oyster Bay enjoy a prime location, just minutes away from Naples’ pristine beaches, upscale shopping at Waterside Shops, and an array of dining options that cater to every palate. The community is also conveniently located near top-rated schools, making it an ideal choice for families.

Whether you’re seeking a serene retreat or a vibrant community lifestyle, Oyster Bay offers the best of both worlds. Explore our current listings and discover the opportunity to own a piece of paradise in this enchanting Naples neighborhood. Your dream home awaits in Oyster Bay!

Newest Oyster Bay Homes for Sale

$3,395,000
3 Beds ⋅ 3 Baths ⋅ 226018001 MLS
Discover an exceptional waterfront retreat in the highly desirable location of Oyster Bay. This unique property offers a total of 160 feet of water frontage, 80 ft on the southern side and 80 feet on the northern side with two private boat docks, two lifts and bridge free access to Naples Bay and Gordon Pass- ideal for avid boaters and adventure seekers. This coastal charmer offers a perfect blend of timeless style, updated interior and open living spaces perfect for entertaining. Stunning water views and endless sunrises and sunsets with preferred southern exposure. This home has been meticulously maintained throughout the years making it an ideal full time/part time residence or an incredible opportunity for redevelopment. Enjoy close proximity to Downtown Naples, world class dining, shopping and beaches.

1420 Jewel Box Avenue, Naples
$3,999,000
3 Beds ⋅ 4 Baths ⋅ 226013587 MLS
Premier waterfront residence at 1510 Chesapeake Ave with direct, no bridge boating access to Naples Bay and the Gulf via Gordon Pass. Set along one of the widest and most navigable canals in Oyster Bay and Royal Harbor, this custom built concrete block home offers a true boater’s lifestyle with distinctive lighthouse inspired architecture and a striking presence. A large double entrance circular driveway and herringbone brick paver entry create a strong first impression. Inside, the home offers three bedrooms plus a den, three and a half baths, soaring ceilings, custom millwork, hand applied trompe l’oeil detail, and abundant natural light that showcases every inch of the interior. The den can easily function as a fourth bedroom. The primary suite and one guest bedroom open directly to the pool, while the additional guest room and den each feature covered outdoor sitting areas, creating a seamless connection to the waterfront setting. From there, the home flows naturally to the dock and spa, extending the living experience outdoors. The custom Ipe hardwood dock, widely regarded as the gold standard in waterfront decking, offers exceptional durability, low maintenance, timeless aesthetic appeal, and a premium gateway to the Gulf. The large garage includes an oversized storage closet, ideal for organizing fishing tackle, rods, boating gear, and other coastal lifestyle essentials. Never flooded and ideally located just minutes from Tin City, Bayfront, Cabana on the Bay, and Downtown Fifth Avenue, this property combines architectural character, premier canal frontage, and exceptional access by both land and water.

1510 Chesapeake Avenue, Naples
$989,000
2 Beds ⋅ 2 Baths ⋅ 226012455 MLS
New Metal Roof! No HOA fees! Private location 1 mile to downtown! Tucked away on a private street in the Royal Harbor area. Boat slips available for lease nearby! Beautiful Old Florida multi-level home with double garage, bonus ground-floor guest/mother-in-law suite with spacious open area, private bath and screened lanai. Spacious and sunny great room design with island kitchen, screened lanai and open deck. The top-quality finishes, open layout and exceptional location near upscale shopping dining and the white sandy Gulf beaches make this home the perfect opportunity to live the Naples lifestyle.

1225 Sandpiper Street, Naples
$7,777,000
5 Beds ⋅ 7 Baths ⋅ 225065690 MLS
Winner of the 2025 Sand Dollar award for Product Design of the Year for Single Family. Welcome to a visionary newly built 2025 contemporary trophy where Architectural Art Meets Waterfront Living. At 1100 Sandpiper design, nature, outdoor living, and technology converge in to timeless elegance. Just one mile from iconic 5th Avenue South and 1.8 miles from the Gulf Beaches, this modern waterfront marvel fuses bold architectural artistry with effortless indoor-outdoor living. With nearly 200 feet of direct Oyster Bay corner frontage, a 60-foot dock already in place (with room for more), and a sculptural form that commands attention from every angle, this is Naples’ ultimate statement home. Rooted in the five natural elements: water, air, earth, fire, and stone -the residence exists in perfect harmony with its environment. Water shimmers from every perspective. Bright light and air drifts through vast glass walls and open terraces. Earth blooms in the lush rooftop lawn and tropical gardens. Fire glows through eight fireplaces across the home. Over 7,500 square feet of natural stone, including 40+ full marble slabs, anchors the structure in enduring sophistication. Outdoor living rivals the interior with nearly equal finished square footage: fully screened waterfront lounges, sunrise and sunset terraces, and secluded open-air zones. The newly completed 1,500-square-foot rooftop sanctuary - complete with sunrise and sunset lounges framed by glass railings—creates a sky-level retreat beyond compare. Inside, nearly 4,000 square feet under air offer five bedrooms, five full baths and two custom half baths. Dual maste suites: one on each level - serve as spa-like havens with luxurious en suites and double vanities as well as a steam shower. 1500 square-foot wraparound terrace seamlessly merges the main living space with the outdoors. Nicknamed The Modern Taj Mahal designed by reendowed Stoff Cooney, this home’s gallery-like glass architecture and structural integrity are unmatched. Built with solid stainless-steel engineered commercial flood panels, it stands among Naples’ most resilient and forward-thinking waterfront builds. Sustainability and innovation shine through a high-output solar roof system with Tesla Powerwalls, a 30+ speaker high-fidelity audio network, and eight fireplaces, including a dramatic centerpiece framing the 12×14 hot tub. The grounds evoke a private resort—three poolside fire bowls, six sculptural water features, and 25+ rare exotic palms illuminated by 100+ warm custom landscape lights. This is far more than a luxury residence: it’s a living masterpiece where art, nature, and modern engineering coexist in perfect balance. Quite simply, Naples’ most visionary home with unprecedented levels of modern luxury & technology in every detail.

1100 Sandpiper Street, Naples
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