Oyster Bay Homes with Canal Access Waterfront features

Oyster Bay Homes with Canal Access Waterfront features

Welcome to Oyster Bay, an enchanting subdivision nestled in the heart of Naples, Florida, within beautiful Collier County. This idyllic community is a haven for those seeking a serene waterfront lifestyle, where every day feels like a vacation. With its picturesque canals and lush tropical landscapes, Oyster Bay offers residents the perfect blend of tranquility and luxury.

Imagine waking up to the gentle sounds of water lapping against your dock, with the sun glistening off the canal just outside your door. Homes in Oyster Bay boast stunning waterfront features, providing direct access to the serene waterways that make Naples so desirable. Whether you're an avid boater, a fishing enthusiast, or simply someone who enjoys the calming presence of water, this community has it all.

The architectural styles of the homes in Oyster Bay are as diverse as the residents themselves, ranging from charming coastal cottages to elegant modern estates. Many properties feature private docks, allowing for easy access to the Gulf of Mexico and its abundant recreational opportunities. Picture yourself enjoying leisurely boat rides, sunset cruises, or fishing adventures right from your backyard.

Beyond the beautiful homes and breathtaking waterfront views, Oyster Bay is conveniently located near Naples’ finest amenities. From upscale shopping and dining to pristine beaches and vibrant cultural attractions, everything you need is just a short drive away.

Oyster Bay is not just a place to live; it’s a lifestyle choice. Experience the magic of waterfront living in this remarkable community and discover why so many call Oyster Bay home. Come and explore the possibilities that await you in this coastal paradise!

Newest Oyster Bay Homes with Canal Access Waterfront features

3 Beds ⋅ 3 Baths ⋅ Oyster Bay SubDv.

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 ⋅ Oyster Bay SubDv.

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 ⋅ Oyster Bay SubDv.

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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Samantha Haringa

Samantha Haringa was born and raised in Massachusetts in the Greater Boston Area. Raised in a family of avid boaters and fisherman with the love for water, sand, and sunsets; moving to Cape Coral was a dream come true. Spending summers as a kid in Marco Island with her grandparents marked the beginning of the pursuit for the lifestyle and passions that the communities of SWFL have to offer. As a resident in the heart of SWFL in Cape Coral, Samantha is a part of the fabric of this vibrant and growing community of families and professionals that are all seeking that same love for the endless summers and treasured sunsets. Coming from a family of entrepreneurs and with twenty plus years of work in client management roles, Samantha has an innate and unrelenting passion for each client’s experience. It’s this passion that drove her to enter the Real Estate Industry. She recognized the singular importance of a client’s experience when buying, selling, or relocating to FL, and the need for a Realtor who would match the enthusiasm and expectations of their clients for this main life event. Plotting a course on the home ownership journey by listening, understanding, and appreciating the stated desires of each client is of paramount importance to her. Samantha’s authenticity, kindness and servant leadership provides every client with the experience of a Realtor whose moral compass remains anchored on the real estate needs and priorities of her clients.

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