Oyster Bay Homes with Canal View

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming subdivision offers an idyllic coastal lifestyle, where sun-soaked days and tranquil evenings come together to create the perfect retreat.

Oyster Bay is renowned for its stunning homes that boast breathtaking canal views, allowing residents to embrace the beauty of waterfront living. Imagine waking up to the gentle lapping of water against your dock, with vibrant sunsets painting the sky in hues of orange and pink as you unwind in your backyard. The canal views not only enhance the aesthetic appeal of these homes but also provide direct access to the waterways, making it a haven for boating enthusiasts and nature lovers alike.

The community is thoughtfully designed, featuring a mix of modern and classic architectural styles that seamlessly blend with the lush, tropical surroundings. Each home is a testament to quality craftsmanship, with spacious layouts and upscale finishes that cater to both comfort and elegance.

Beyond the stunning residences, Oyster Bay is conveniently located just minutes away from Naples' pristine beaches, upscale shopping, and gourmet dining options. Whether you’re strolling along the shoreline, exploring the local art scene, or indulging in a culinary adventure, you’ll find that everything you need is right at your fingertips.

Discover the charm and allure of Oyster Bay, where a vibrant lifestyle and serene canal views await. Your dream home in this enchanting community is just a visit away!

Newest Oyster Bay Homes with Canal View

$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.