Oyster Bay Real Estate

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida. This picturesque subdivision is renowned for its serene waterfront living, where the gentle sounds of the waves and the lush, tropical landscapes create an idyllic backdrop for your dream home.

Oyster Bay boasts a unique blend of luxury and tranquility, offering residents a peaceful retreat while still being just minutes away from the vibrant life of downtown Naples. With its proximity to the stunning Gulf of Mexico, residents can easily indulge in sun-soaked days at the beach, enjoy thrilling water sports, or take leisurely strolls along the picturesque shoreline.

The community is characterized by its elegant homes, many of which feature private docks and breathtaking views of the bay, making it a prime location for boating enthusiasts. The lush greenery and mature trees lining the streets create a welcoming atmosphere that invites you to explore and enjoy the outdoors.

Families will appreciate the top-rated schools in the area, along with a wealth of recreational opportunities, including nearby parks, golf courses, and upscale shopping and dining options. Whether you’re looking for a cozy family home or a luxurious waterfront estate, Oyster Bay offers a diverse range of properties to suit every lifestyle.

Discover the charm of Oyster Bay, where coastal living meets sophisticated elegance, and experience the unparalleled quality of life that Naples has to offer. Your dream home awaits in this enchanting community!

Newest Listings in Oyster Bay

$550,000

2026024008 MLS

Discover a rare opportunity to own two contiguous premier marsh front homesites in the highly sought after Oyster Bay Harbour community. With two lots, buyers have the opportunity to create an expansive homesite, accommodate a larger floor plan, enhance outdoor living spaces, and preserve additional privacy. These expansive lots offer over two acres of combined waterfront living, showcasing breathtaking panoramic marsh views and spectacular sunrises over Amelia Island. Enjoy the tranquiltiy of marsh front living while remaining just minutes from historic downtown Fernandina Beach, Amelia Island's renowed beaches, championship golf, fine dining and world class boating and fishing. Residents of Oyster Bay Harbor enjoy a gated community known for its luxury homes, natural beauty and proximity to the Intracoastal waterway. One of Oyster Bay Harbour's most coveted amenities is the private Oyster Bay Yacht Club and Marina. The marina provides direct access to the Intercoastal Waterway and Atlantic Ocean, making it an ideal home base for boating enthusiasts. Property owners also have access to the Oyster Bay Yacht Club lifestyle, featuring waterfront dining, social activities, marina amenities, and a vibrant coastal community atmosphere. Whether you're looking to build your forever home, a coastal retreat, or secure a premier homesite in one of Northeast Florida's most desirable communities, this unique double-lot offering presents an exceptional opportunity.

96600 & 96588 Soap Creek, Fernandina Beach

$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

$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 ST, Naples

$7,777,000

5 Beds ⋅ 6.5 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 ST, 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.