Oyster Bay Homes with Boat Dock Private Exterior Features

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming subdivision offers a unique blend of tranquility and luxury, making it an ideal destination for those seeking a coastal lifestyle. Known for its serene waterways and stunning natural beauty, Oyster Bay is the perfect setting for boating enthusiasts and nature lovers alike.

Oyster Bay boasts a variety of exquisite homes, many of which feature private boat docks, allowing residents to embrace the ultimate Florida lifestyle. Imagine stepping out of your beautifully appointed residence and onto your boat, ready to explore the scenic waterways of Naples. With direct access to the Gulf of Mexico, your weekends can be filled with sun-soaked adventures, fishing trips, or leisurely cruises along the coastline.

Each home in Oyster Bay is designed with attention to detail, showcasing luxurious finishes and spacious layouts that cater to both relaxation and entertainment. The exterior features of these properties are equally impressive, often highlighting lush landscaping, outdoor living spaces, and, of course, those coveted private docks. Whether you’re hosting a sunset gathering with friends or enjoying a quiet evening by the water, the outdoor spaces in Oyster Bay provide the perfect backdrop.

Living in Oyster Bay means being part of a vibrant community that values both privacy and connection. With its prime location in Naples, residents enjoy easy access to world-class dining, shopping, and entertainment, all while being surrounded by the natural beauty that Florida is renowned for. Experience the allure of Oyster Bay—where your dream home and a life on the water await!

Newest Oyster Bay Homes with Boat Dock Private Exterior Features

$3,095,000

3 Beds ⋅ 3 Baths ⋅ 226034349 MLS

A rare waterfront offering in Oyster Bay, 1420 Jewel Box Avenue captures the best of Naples living. With 160 feet of water frontage across two sides of the property, two private docks, two boat lifts, and bridge-free access to Naples Bay and Gordon Pass, this is an exceptional setting for those who want to spend their days on the water. Southern exposure brings natural light into the home and sets the stage for sweeping water views, sunrises, and sunsets. Inside, updated interiors and open living spaces offer an inviting setting for entertaining or a quiet retreat after a day on the boat. Meticulously maintained, the home is equally suited to year-round living, a seasonal escape, or the opportunity to create a new waterfront residence. Just minutes from downtown Naples, acclaimed dining, shopping, and the Gulf beaches, this distinctive property pairs a coveted boating location with remarkable possibilities.

1420 Jewel Box AVE, Naples

$7,995,000

5 Beds ⋅ 5.5 Baths ⋅ 226032953 MLS

Brand-new contemporary construction minutes from Fifth Avenue South, the heart of Naples. Designed by award-winning Greg Weber of South Florida Design, this three-story residence runs nearly 8,000 square feet under roof, including nearly 4,400 square feet of elevated living area. A dramatic three-story glass entry opens to five bedrooms, five full baths, a powder room and a private elevator serving every floor. The fifth bedroom is presently appointed as a private office, an elegant work-from-home retreat that reverts to a guest suite whenever needed. The living, dining and kitchen face west towards the water, placing the harbor and the sunset in view from the moment you step inside. Walls of glass, soaring ceilings, custom built-ins and exceptional lighting throughout. The chef's kitchen pairs custom cabinetry with an oversized island, a professional gas range, integrated appliances and a separate wet bar built for entertaining. The primary suite is a quiet sanctuary, with abundant natural light, a spa-inspired bath and custom boutique-scale closets. An east–west sightline runs to the outdoor living spaces, where an outdoor kitchen, relaxed seating, TV and fireplace overlook the elevated heated pool and spa for year-round enjoyment. Mature tropical landscaping and privacy screening make it feel enclosed and entirely private. The ground level offers what other homes do not: a climate-controlled four-car tandem garage alongside ~1,600 square feet of finished, fully conditioned storage with direct interior access — rare square footage in Naples. A reinforced perimeter landscape wall surrounds the property, with an integrated flood panel system and emergency generator for added peace of mind. The deeded boat slip is directly across the street, just out the front door, with a private lift, a City-maintained seawall and no-bridge access to Naples Bay and the Gulf. No canal turns, no clearance math, no bridge waits. Offered fully furnished. Fifth Avenue South dining, galleries, shopping and the beach are minutes away, with Naples and Fort Myers airports an easy drive. New, elevated, west-facing, downtown-adjacent, and boat-ready on day one.

1085 SANDPIPER ST, Naples

$3,899,000

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

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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.