Oyster Bay Homes with Canal Access Waterfront

Oyster Bay Homes with Canal Access Waterfront

Welcome to Oyster Bay, a hidden gem nestled in the picturesque city of Naples, Florida, within the lush landscapes of Collier County. This charming waterfront community is renowned for its stunning homes with canal access, offering residents the perfect blend of luxury and tranquility.

Imagine waking up each morning to the gentle sounds of water lapping against your private dock, where your boat awaits for a day of exploration along the scenic waterways of Southwest Florida. Each home in Oyster Bay boasts exquisite architectural designs and modern amenities, ensuring a lifestyle of comfort and elegance. With spacious floor plans, expansive outdoor living spaces, and breathtaking views, these residences are a true reflection of coastal living at its finest.

Oyster Bay is not just about beautiful homes; it’s a vibrant community that embraces the Florida lifestyle. Residents enjoy easy access to pristine beaches, world-class dining, and upscale shopping, all while being surrounded by the natural beauty of lush mangroves and serene canals. Whether you’re an avid boater, a nature enthusiast, or simply seeking a peaceful retreat, Oyster Bay offers a unique opportunity to indulge in the best of what Naples has to offer.

With its prime location and exceptional waterfront properties, Oyster Bay is more than just a place to live; it’s a lifestyle waiting to be embraced. Discover the charm and elegance of this remarkable community, where every day feels like a vacation in paradise. Come home to Oyster Bay—your waterfront oasis awaits!

Newest Oyster Bay Homes with Canal Access Waterfront

1420 Jewel Box Avenue, Naples
$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 Avenue, Naples
1085 SANDPIPER Street, Naples
$7,995,000
5 Beds ⋅ 6 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 Street, Naples
1095 Sandpiper Street, Naples
$3,295,000
3 Beds ⋅ 2 Baths ⋅ 226030870 MLS
MUST-SEE FULLY REMODELED WATERFRONT HOME — DESIGNED TO THE MAX! TWO BOAT SLIPS with lifts! Prepare to be impressed by this extraordinary, fully remodeled home where luxury, sophistication, and the ultimate Naples lifestyle come together. Every detail has been thoughtfully designed and beautifully executed, creating a truly exceptional residence that is partially furnished and move-in ready. The stunning chef’s kitchen is the heart of the home, featuring high-end appliances, designer fixtures, custom finishes, and an impressive 14-foot island that provides the perfect gathering space for family and guests. The open, sophisticated design seamlessly connects the kitchen to the main living areas, creating a spectacular setting for both everyday living and entertaining. Step outside to the expansive marble front patio, where breathtaking views of the bay create an unforgettable backdrop. With two boat slips, this property offers an incredible opportunity for boating enthusiasts to enjoy the waterfront lifestyle right from home. The large backyard patio is an entertainer’s dream, complemented by a heated saltwater pool perfect for relaxing, dining, and hosting guests. Whether enjoying a quiet afternoon by the pool or entertaining friends and family, this outdoor space is designed to make the most of the beautiful Naples lifestyle. Additional upgrades include a new roof and new custom wrought-iron doors, adding timeless elegance and peace of mind. No detail was overlooked in this exceptional renovation. Ideally located in the heart of Naples, this remarkable property puts you close to the best the area has to offer while providing the luxury, waterfront setting, and boating lifestyle you've been searching for. This is more than a home — it’s a Naples lifestyle. Truly a must-see!

1095 Sandpiper Street, Naples
1510 Chesapeake Avenue, Naples
$3,899,000
3 Beds ⋅ 4 Baths ⋅ 226013587 MLS
Direct, no-bridge boating access to Naples Bay and the Gulf via Gordon Pass defines this waterfront home in Oyster Bay. A private Ipe dock with boat lift, screened heated pool and spa, and covered outdoor dining area make the canal setting central to everyday living. The custom concrete block home offers 3,062 square feet of living space with three bedrooms plus a den and three and a half baths. Distinctive lighthouse-inspired architecture, soaring ceilings, custom millwork, decorative painted details, and abundant natural light give the interior its character. The split-bedroom layout provides separation for guests, while the den offers space for a home office or additional sitting room. The primary suite and one guest bedroom open directly to the pool, while the additional guest bedroom and den each feature covered outdoor sitting areas. A circular paver driveway welcomes guests, and the attached two-car garage includes an oversized storage closet for fishing tackle, boating gear, and other essentials. Enjoy waterfront living close to Tin City, Bayfront, and the dining and shopping of Fifth Avenue South.

1510 Chesapeake Avenue, Naples
1390 Chesapeake Avenue Unit 1390, Naples
$1,499,000
3 Beds ⋅ 2 Baths ⋅ 226013181 MLS
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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