Oyster Bay Naples Real Estate - 2 Homes, 15 Condos For Sale

Offering spectacular waterfront living at it's finest is this crowning jewel of Jewel Box Avenue. Residing at the point of Chesapeake canal and Naples Bay stands this 4 bedroom en-suite estate with panoramic west facing water views from nearly every room. Owners will enjoy the first floor primary en-suite with 2 large walk in closets, huge primary bath with separate shower and soaking tub. Steps from the primary bed is a cozy outdoor sitting area with electric (remote controlled) retractable screens and shutters to enjoy the amazing sunsets over the bay. Guest will enjoy the second floor privacy with elevator access. Each en-suite has its own wrap around balcony access with spacious lounge areas and west facing water views. Additionally the second floor offers multiple en-suite wet bars, sitting area and media room that could easily be used as a 5th bedroom. Perhaps the star of the show is the nearly 8000 sq-ft of outdoor living space with waterfront infinity edge pool, 2 spas, outdoor kitchen, pool bath and multiple docks and boat lifts. Boaters will appreciate this section of Naples Bay is a no wake zone and the home resides well away from the channel marked area thus offering peace and quiet calm waters. Additionally the boat lifts have been strategically installed on the north canal side of the property offering further protection. The area has recently undergone extensive dredging and this property can dock larger vessels with a 24,000 lbs boat lift and 13,000 lbs jet ski/kayak platform lift. The list of upgrades to this home are extensive with a recent 7 figure renovation and refurnishing which WAS NOT a result of flooding or any storm damage. If you are looking for a well built turnkey waterfront property that lives like a high end resort 1340 Jewel Box should be considered.

Experience waterfront living in this stunning four-bedroom ranch-style residence offering direct, deep-water Gulf access and exceptional privacy. This high and dry property has never experience any storm flooding or damage. Positioned with desirable southern exposure, the home captures tranquil views of lush mangroves and picturesque boat docks, creating a serene Naples backdrop. A highlight of the property is the expansive 1,000-square-foot private dock, ideal for boating enthusiasts, sunset lounging or hosting unforgettable gatherings by the water. Inside, the home features a gourmet kitchen designed to impress, complete with a spectacular 14 foot custom island, premium finishes, and seamless flow for everyday living or entertaining. The elegant dining room includes an integrated built-in bar, offering a sophisticated space for hosting friends and family. Additional features include a three-car garage, spacious bedrooms, and an inviting single-level layout that embodies comfort and coastal ease. Just minutes from 5th Avenue’s renowned shops and fine dining, this home offers the ideal blend of luxury, convenience and waterfront charm. A must-see for those seeking exceptional Naples living.

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 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.

Luxury and lifestyle meet in this stunning, elegant, and serene waterfront villa. This captivating end-unit villa in Oyster Bay offers sweeping western sunset views and direct Gulf-access waterfrontage. Nestled on a quiet cul-de-sac just minutes from downtown Naples, it seamlessly blends bright, light-filled interiors with expansive outdoor spaces, creating an idyllic coastal boating paradise. The 2,107-square-foot residence centers around a sun-drenched open living area featuring beautiful wood floors, designer fixtures, and a built-in fireplace that connects the charming interior courtyard to the waterfront backyard. The chef’s kitchen impresses with custom cabinetry, premium quartzite countertops, stainless-steel appliances, a coveted gas cooktop, integrated wine cooler, wet bar, and breakfast bar. Thoughtfully designed across two levels, each bedroom is upstairs and delivers a unique tranquil escape, a private bathroom, and a dedicated outdoor space. The primary suite, with walk-in closet and spa-like ensuite bathroom is a showstopper with unobstructed panoramic sunset views from its west facing balcony. In addition to another bedroom, full bathroom, and study, the second floor includes a guest suite with its own spiral staircase access from the interior courtyard, a kitchenette, and sitting area. The unique outdoor space of this villa is really what sets it apart with an intimate courtyard, sunlit private pool and spa, and extended Southern facing deck. For the boaters, access to the Gulf is quick and easy with no bridges, and the generous 40-foot boat dock can accommodate a vessel up to 34' and a future boat lift. Surrounded by lush tropical landscaping, the property also includes a two-car garage, an extra parking space, and paved area for two-wheeled transportation. Built for resilience, it features impact-resistant windows and doors, a newer roof, and elevated construction that remained dry through multiple storms. Minutes from downtown Naples’ vibrant 5th Avenue South, world-class beaches, shopping, and dining, this rare southern-exposure waterfront gem perfectly embodies luxury, comfort, and the quintessential Naples lifestyle.

Nestled in the highly sought-after Oyster Bay neighborhood, this beautifully renovated top-floor condo offers the perfect blend of waterfront living and modern design. Located on a quiet canal with direct access to Naples Bay and the Gulf—no bridges—this rare opportunity includes a 24-foot deeded boat slip, ideal for enjoying the tranquil backwaters or heading out for a day on the Gulf. Inside, the 3-bedroom, 2-bath end unit layout showcases thoughtful redesigns, including refined doorways and selectively reimagined walls that enhance flow and create a more open, connected feel with lots of light and windows. Volume ceilings and an airy open-concept floor plan provide a sense of spaciousness, while a screened lanai invites you to relax and take in peaceful water views. The spacious primary suite offers a walk-in closet and spa-inspired bathroom, and a full-size laundry room adds convenience to everyday living. Built in 2007 with solid concrete block construction, this residence also features impact-rated windows and doors, as well as a rare two-car plus enclosed garage. A common elevator or stairwell provides easy access to the top-floor unit. Residents also enjoy a community pool, perfect for cooling off or socializing after a day on the water. Just minutes from the fine dining and boutique shopping of 5th Avenue. Whether you're a boater, beach lover, or seeking the quintessential Naples lifestyle, this property delivers it all.

COMPLETELY RENOVATED 2/2, end unit condo with beautiful views located in Oyster Bay!!!! Boat Slips available for lease from the community for only $300.00 per year!!!!! Brand New Seawall, Dock and Roof installed in 2025!!! You can walk to Olde Naples or enjoy time out on the dock. Extremely peaceful! Low density! The newly added and updated Florida room with new windows under air allows you to enjoy breakfast/lunch or dinner overlooking the pool and canal. Blue Point allows up to 12 rentals a year with a minimum 30 day lease, providing flexibility for personal use, investment or both!! Over 53k in rental income in 2023!! Renovations include but not limited to - ALL NEW - gourmet appliances, washer/dryer, wine cooler, stand alone icemaker, under cabinet lighting, quartz countertops, fixtures/hardware throughout, doors interior & exterior, light Oak hardwood flooring throughout, bathroom vanity's, tile, toilets, custom shower doors, Samsung tv's, Sonos system, Nest thermostat, Ring doorbell, recessed LED can lighting, ceiling fans, all furniture! 100% TURNKEY!!! Don't miss out on this opportunity to buy in Royal Harbor/Oyster Bay before completion of Metropolitan Naples on the corner of 41 and Davis Blvd!!!

El Nido is a small enclave of four condominiums in the Royal Harbor area with direct Gulf access from your deeded boat dock. Just minutes from downtown Naples and the Gulf beaches. Spacious 2+den with volume & tray ceilings. Tile flooring throughout with Plantation Shutters on the windows. Both bedrooms have large walk-in closets, with the primary ensuite having both a soaking tub and separate shower. This community has a large pool and hot tub surrounded by brick pavers, and a sun deck that leads out to your boat dock. Building updates include a new roof in 2022, pool and pool deck in 2023, and the exterior painted in 2024.

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.

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.

Enjoy the charm of downtown Naples with this beautifully updated second-floor condo with an incredible unobstructed water view at the Sea Eagle. Ideally located, you're just a short stroll to the vibrant shops and dining of Fifth Avenue South and scenic Bayfront. This spacious 2-bedroom, 2-bath residence includes a private boat dock with direct Gulf access—no bridges!—perfect for boating enthusiasts. The unit also comes with a designated covered parking space for added convenience. Inside, you'll find a fully remodeled kitchen and bathrooms, featuring quartz countertops and sleek, modern finishes. The light-filled living space opens to tranquil water views, creating a relaxing coastal atmosphere. The Sea Eagle is a boutique community of only 18 units, recently repainted and impeccably maintained. Residents enjoy access to a community pool, a covered gathering area, grilling station, and a shared boat dock. Experience the luxury and lifestyle of waterfront downtown living—at a fraction of the cost of other similar properties.

This two-bedroom, two-bathroom condo is professionally remodeled, fully furnished, and stayed high and dry during hurricanes, offering everything you need for your Gulf Coast living lifestyle. It has undergone a complete transformation, featuring an expanded kitchen, bathrooms, flooring, appliances, and a complete electrical overhaul (new sliding glass doors will be installed soon). The new space features quartz countertops, generous seating, and sophisticated finishes throughout, including wide oak vinyl flooring and large porcelain tiles in the bathrooms. The spacious living area opens to a screened lanai and private patio, offering tranquil views of the water and your new seawall, new wooden deck, and deeded 30-foot boat slip with unrestricted access to the Gulf of Mexico. Residents enjoy exclusive amenities such as private storage, heated pool, social clubhouse, BBQ area, and newly constructed seawall and decking, all within a vibrant 55+ community. This is the perfect time to find your next home in beautiful Naples, FL, and still be able to enjoy our award-winning beaches, shopping, and dining just moments away. Whether you’re interested in year-round Florida living or want to enjoy a few months out of the winter snow, this gorgeous condo is just right for you.