Oyster Bay Homes with Canal Front Waterfront type

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida, within Collier County. This enchanting subdivision offers a unique blend of luxurious living and serene waterfront charm that is hard to resist. Known for its picturesque canals and stunning waterfront properties, Oyster Bay is the perfect oasis for those who appreciate the beauty of nature and the allure of coastal living.

Imagine waking up each morning to breathtaking views of shimmering waters right outside your window. The homes in Oyster Bay are designed with elegance and comfort in mind, featuring spacious layouts, modern amenities, and exquisite finishes. Many of these properties boast direct canal front access, allowing residents to enjoy a myriad of water activities such as boating, fishing, and paddleboarding right from their backyards.

Beyond the stunning homes, Oyster Bay offers a close-knit community atmosphere, where neighbors become friends and outdoor adventures await at every turn. The lush landscaping and tranquil surroundings create an idyllic setting for families and retirees alike. With Naples' renowned beaches, upscale shopping, and fine dining just a short drive away, residents can enjoy the best of both worlds—secluded living with easy access to the vibrant lifestyle that Naples has to offer.

Whether you are seeking a year-round residence or a vacation retreat, Oyster Bay promises a lifestyle of luxury and leisure. Come discover the beauty and tranquility of this magnificent waterfront community, where your dream home awaits!

Newest Oyster Bay Homes with Canal Front Waterfront type

$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 AVE, Naples

$3,999,000

3 Beds ⋅ 3.5 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 AVE, Naples

$1,499,000

3 Beds ⋅ 2 Baths ⋅ 226013181 MLS ⋅ Oyster Bay BLDG.

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 AVE Unit 1390, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.