Oyster Bay Homes with Canal Access Waterfront

Oyster Bay Homes with Canal Access Waterfront

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida, within the beautiful Collier County. This enchanting waterfront community is perfect for those seeking a tranquil lifestyle combined with the vibrant charm of coastal living.

Oyster Bay boasts a unique selection of homes that offer direct canal access, allowing residents to indulge in the ultimate Florida lifestyle. Imagine stepping out of your backyard and onto your boat, ready to explore the stunning Gulf waters or enjoy an afternoon of fishing in the serene canals. Each home in this picturesque community is designed to maximize the breathtaking views, providing a seamless blend of indoor and outdoor living spaces.

The architectural styles in Oyster Bay are as diverse as the residents themselves, featuring everything from charming coastal cottages to elegant contemporary estates. Each property showcases meticulous craftsmanship and luxurious finishes, ensuring a comfortable and stylish living experience. With lush landscaping and private docks, these homes create an inviting atmosphere that is perfect for entertaining family and friends or simply unwinding after a long day.

Beyond the stunning homes, residents of Oyster Bay enjoy proximity to Naples' renowned beaches, upscale shopping, and gourmet dining options. With a vibrant arts scene and a plethora of outdoor activities, this community offers something for everyone.

Discover the allure of Oyster Bay, where waterfront living meets the best of Naples. Embrace a lifestyle filled with sunshine, relaxation, and endless opportunities for adventure. Your dream home awaits in this idyllic paradise!

Newest Oyster Bay Homes with Canal Access Waterfront

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 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

3 Beds ⋅ 2 Baths ⋅ 226013181 MLS

Completely renovated 3 bedroom, 2 bath, TURNKEY furnished BY ARHAUS, waterfront condo on Naples Bay with Direct Gulf access & 26 ft Boat Slip, NEW ROOF JULY 2026. The interior has been COMPLETELY RENOVATED and NEVER LIVED-IN with luxury finishes and elegant Arhaus furnishings throughout creating a stylish and functional living space including impact windows and doors. Second floor end unit with additional windows flood the home with natural light and stunning bay views. Outdoor living is elevated with a lanai overlooking the water perfect for enjoying spectacular sunsets from this tranquil setting. This boutique community consists of only 6 residences with low Condo Fees, offering a private exclusive atmosphere minutes to 5th Avenue, 3rd Street, the city's world class shopping, dining, arts and white sandy beaches.

1390 Chesapeake Avenue Unit 1390, Naples

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