Oyster Bay Naples Real Estate - 3 Homes, 15 Condos For Sale

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.

Discover an exquisite waterfront sanctuary at 1506 Jewel Box Avenue, perfectly positioned on one of Royal Harbor’s widest canals. This exceptional property offers an impressive 130 feet of total water frontage with two private docks and bridge-free access to Naples Bay and the Gulf waters—ideal for avid boaters seeking seamless adventures on the water. Completely transformed into a sophisticated modern masterpiece, this 2,777-square-foot residence has never flooded and sits at 10.25 feet elevation. Its design thoughtfully blends organic materials with cutting-edge smart technology, and every detail has been meticulously curated for beauty, functionality, and enduring value. The open living spaces feature soft hardwood floors, recessed LED lighting, upgraded interior doors, designer fixtures, and striking architectural ceiling beams. A desirable split floor plan centers around an expansive, panoramic screened lanai with a resort-style pool, promoting effortless transitions between formal and casual living, indoor elegance, and outdoor relaxation. The gourmet kitchen is a chef’s dream, equipped with premium brushed black Samsung appliances, natural stone countertops, soft-close wood cabinetry, a generous breakfast bar, convenient recessed charging station, and subtle under-cabinet toe-kick lighting. The luxurious primary suite serves as a private waterfront retreat, complete with serene canal views, dual walk-in closets, and a spa-inspired bathroom featuring a freestanding soaking tub, separate rain shower, dual vanities with backlit LED mirrors, and a state of the art smart toilet. On the opposite wing, two additional bright and spacious bedrooms offer ample closet space for ultimate privacy. A versatile fourth bedroom with double French doors doubles perfectly as a home office, den, or meditation room. The multifunctional laundry room elevates everyday convenience with custom cabinetry, a utility sink, built-in drying racks, and direct access to the climate-controlled two-car garage. Outdoor living is equally impressive, designed for year-round enjoyment. The pool area boasts a sun shelf, integrated spa, elevated swing seating, custom dynamic lighting, and built-in fountains. A third full bathroom is conveniently tucked under the covered lounge with a built-in gas fireplace. Landscape lighting creates magical ambiance throughout the entry garden, rear deck, and docks. What truly distinguishes this home is its unparalleled boating lifestyle. The rear features an expansive Trex deck with outdoor shower, sun lounge area, swim platform and a 65-foot dock. Across the street, an additional 65-foot dock includes a 30,000-pound boat lift and protective canopy, plus four bonus parking spaces. All this awaits on a peaceful, quiet street in the prestigious Royal Harbor neighborhood—minutes from downtown Naples’ world-class dining, shopping on 5th Avenue South, and pristine Gulf beaches. Experience refined coastal living at its finest!

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.

Discover a blend of luxury, comfort and unbeatable Royal Harbor location in this beautifully updated townhouse offering over 2,000 square feet of spacious living. This three-bedroom, 3.5-bath residence includes a private guest suite with its separate entrance, ideal for visitors or extended stays. Enjoy your private courtyard oasis complete with a sparkling pool, ideal for relaxing or entertaining. With a private boat dock offering deep, direct water access to Naples Bay and the Gulf, this home is a boater’s dream. Less than three miles from the beach and just a short walk to 5th Avenue and downtown Naples, you’ll have world-class dining, shopping and entertainment moments from your door. This pet-friendly townhouse also features a two-car garage, modern finishes throughout and bright, open living spaces designed for effortless coastal living. Experience waterfront living at its finest as this exceptional property has it all.

A rare opportunity of a one-of-one property in the highly sought-after Oyster Bay enclave of Naples. Perfectly positioned on the shimmering waters of Naples Bay, this exceptional waterfront residence captures truly breathtaking, unobstructed bay views, modern elegance, and direct boating access to the Gulf. Completely renovated and thoughtfully reimagined, the home offers stunning vistas from nearly every living space — including the main living area and both bedrooms — creating a seamless and constant connection to the tranquil coastal setting. Tucked away at the end of a peaceful cul-de-sac, the property includes a deeded boat dock with immediate Gulf access, making it a boater’s dream. Coveted Southern and Western exposures flood the residence with natural light throughout the day and provide a spectacular backdrop for Naples’ renowned sunsets, best enjoyed from the comfort of two private balconies. Inside, a refined contemporary aesthetic defines the fully updated interior. Luxury flooring flows throughout the residence, complemented by a stylish chef’s kitchen featuring stainless steel KitchenAid appliances, quartz and quartzite surfaces, soft-close cabinetry, and modern designer lighting. Motorized blinds and impact-resistant windows and doors offer both convenience and peace of mind. Both bathrooms have been beautifully renovated with spa-inspired finishes, sleek vanities, and spacious walk-in showers, delivering a true retreat experience. Outdoor living is equally captivating, with two private balconies offering peaceful spaces to relax and take in the ever-changing waterfront scenery. The energy of Naples Bay comes alive daily — from dolphins and manatees gliding through the water to the mesmerizing parade of passing boats — creating a dynamic yet tranquil coastal backdrop that is uniquely Naples. Located within the intimate waterfront community of Chesapeake Point, residents enjoy a quiet and private atmosphere just minutes from the vibrant energy of downtown Naples. World-class dining, boutique shopping, and cultural attractions along Fifth Avenue South are easily accessible by foot or bicycle. Whether as a full-time residence or seasonal coastal escape, this extraordinary bayfront property embodies refined waterfront living in one of Naples’ most desirable locations.

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.

Stop dreaming and start living location, elegance and boater's paradise are converged in this 1,960-square-foot Royal Harbor gem! This isn't just a condominium, it's a direct Gulf-access lifestyle with no bridges standing between you and open water. Whether you're guiding your boat from your private 28-foot dock to Keewaydin island or enjoying sunset views of Naples Bay from your south-facing balcony, the Gulf is practically your backyard. Outside, new docks and a recently renovated heated pool are featured. Inside, the two-floor condominium features travertine flooring, elegant tray ceilings, and a spacious kitchen complete with stainless steel appliances and granite countertops. Upstairs, you'll find two oversized primary en suites with their private balconies. Whether you're biking to the sugar sand beaches or dining on 5th Avenue South, this is the permanent vacation you've been waiting for.

Welcome to your Waterfront Escape - this beautifully maintained first-floor, 3-bedroom, 2-bathroom furnished condo offers the perfect blend of comfort, convenience, and coastal living. Step inside to find a bright, open layout with tasteful furnishings throughout, making this home truly move-in ready. This spacious living and dining areas flow seamlessly to a screened lanai, where you can relax and enjoy tranquil canal views and gentle breezes. The kitchen is well-dashed appointed, with ample cabinetry and counter space, ideal for both everyday living and entertaining. The primary suite features a private bath and generous closet space, while two additional bedrooms provide flexibility for guests, a home office, or family living. What truly sets this property apart is the included deeded 25ft boat dock with lift, offering direct canal access - perfect for boating enthusiasts looking to get on the water with ease. Additional highlights include convenient first-floor access, elegantly furnished for immediate enjoyment or rental potential, laundry in residence, assigned parking, and peaceful waterfront setting. Whether you're seeking a fulltime residence, seasonal retreat or investment opportunity, this condo delivers the ultimate Florida lifestyle -just minutes from open water and dining and shopping on 5th Ave, 3rd Street, and Bayshore Drive. Boat, relax, and live the waterfront Dream!

A BOATER’S HAVEN!! Includes an assigned 26 Foot Boat Slip with a 10,000 lb. Lift - no bridges to Gulf and just 4 steps off Lanai to your boat This completely renovated 1.5 bdrm./2 bath condo is a truly must see for the most discerning buyer. Some upgrades and renovations include, porcelain tile flooring throughout, impact resistant windows and door, Quartz countertops with full size backsplash, superior full wall cabinets with pull-outs and lazy susan, quartz kitchen island with cabinets and overhead fan, newer upgraded stainless steel appliances, plantation shutters on all windows, expansive master bedroom offers 20 feet of closet space. Both bathrooms have been exquisitely refinished, and the list goes on and on. A complete list of improvements and upgrades can be provided. Location is everything and you are a mile from downtown, beaches and all that Naples has to offer.

Step into this move-in-ready, well maintained, fully updated condo and experience the best of Naples waterfront living. This 2-bedroom, 2-bath home sits directly on a canal with partial Naples Bay views, overlooking the Tin City area—and offering stunning sunsets each evening from the comfort of your own space. With 5th Avenue South, 3rd Street, and multiple Gulf beach access points just 5–10 minutes away, you’ll enjoy unmatched proximity to Naples’ top boutiques, restaurants and pristine beaches. A deeded 26' boat dock is included, providing direct access to the bay. Cruise to Tin City or Bayfront for dinner, fish the nearby mangroves or open Gulf, or head to famous Keewaydin Island—just a short ride by boat. The condo features a long list of recent upgrades: brand-new hurricane-impact windows with a transferable warranty, a new roof and electrical service, updated kitchen and bathrooms, a new soaking tub, new flooring, and a 2-year-old AC system and appliances. The community pool is being fully renovated, and the assessment has already been covered. This is a rare opportunity to own a beautifully updated waterfront home in a prime Naples location—without the long commute from the outskirts. Whether you’re seeking a vacation getaway or a full-time residence, this condo offers convenience, comfort, and nightly sunsets that make every day feel like a getaway.

Bridge-free Gulf access meets true condo convenience: this spacious 3-bedroom, 2.5-bath, two-story residence offers approx. 1,835 sq ft and includes an assigned 40’ boat slip with water and electric at the dock. The oversized living room opens onto a screened waterfront balcony overlooking the canal, and the open kitchen features bright shaker cabinetry, stone counters, stainless steel appliances, generous storage, and a dedicated laundry room. Floor plan features multiple balconies for indoor-outdoor living, with a powder bath on the main level and all bedrooms upstairs. Clam Court is a tucked-away waterfront community in Oyster Bay featuring a community pool and clubhouse/community room, plus a fish-cleaning station and BBQ/picnic area—ideal for boating days and casual waterfront living. Enjoy bridge-free access out to Naples Bay and the Gulf, with an unbeatable in-town location just minutes to Fifth Avenue South, downtown Naples, and the beaches. Virtual Staging is used in some photos.

Low HOA dues include flood insurance! Presenting the fully furnished and renovated 08/24 waterfront property you have been waiting for! Rarely available, this property is directly on the water, providing direct gulf access, a large outdoor living space and deeded dock. This property lives extremely private. Peace of mind is assured with impact windows and sliders. The seller has not spared any expense fully renovating this condo from head to toe. Simply bring your boat and enjoy the Naples waterfront lifestyle at a fraction of the cost. This unit is priced to sell and will not last long. Secure your tropical oasis today!