Oyster Bay Naples Real Estate - 1 Home, 21 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. 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 9-foot 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.

Investors - endless potential - prime investment opportunity on the water in Naples and close to downtown 5th Avenue, Naples. This well-maintained, solid concrete block construction quadruplex on the water offers four units with excellent income potential. Six ample parking spaces, a large shared heated pool, with a 6-foot privacy fence give the occupants a perfect getaway retreat. Each furnished unit has two full baths and two full bedrooms, a fully equipped kitchen with granite countertops, laundry room, dining room, open-concept living room (second-floor units have vaulted ceilings in living area) and a lanai overlooking the water. Each unit has wood/tile flooring, plantation shutters, custom glass shower doors and new ceiling fans. First-floor units offer a conjoining door that allows for the entire first floor to be shared as one unit. (Perfect for a large family.) Each unit can be rented individually. Boaters enjoy a brand new 60-foot boat dock with composite decking, boat slip equipped with bumpers to protect your vessel and quick, no-bridge access to Naples Bay and the Gulf. Your vision, your opportunity!

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.

STUNNING WATERFRONT CONDO ON NAPLES BAY WITH DIRECT GULF ACCESS & 26 FT BOAT SLIP INCLUDED!! Experience the ultimate Naples lifestyle in this beautifully renovated 2-bedroom + den, 2-bath waterfront condo, ideally located in a boutique community of just six residences at the end of a quiet cul-de-sac in downtown Naples. Boasting breathtaking panoramic views of Naples Bay and the canal, this high and dry, second-floor unit offers direct boating access to the Gulf of Mexico—no bridges, just a short ride through Gordon Pass. Your private 26 ft boat slip makes it easy to enjoy boating, fishing, or sunset cruising anytime. Inside, this designer-renovated condo features wood and tile flooring, stone countertops, and updated bathrooms designed for comfort and efficiency. The chef’s kitchen, light-filled interiors, and open-concept living space are complemented by multiple outdoor areas, including a rear balcony and front covered lanai, perfect for entertaining or relaxing while watching dolphins, birds, and sunsets over the water. This turnkey-furnished home also includes covered parking, a private storage room, and is located in a pet-friendly, low-fee community. This exceptional waterfront condo includes a 26-foot private boat slip with no bridges to the Gulf, offering unmatched boating access through Gordon Pass. The interior has been completely renovated with wood and tile flooring, stone countertops, and updated bathrooms, creating a stylish and functional living space. With 2 spacious bedrooms, a flexible den or office space, and 2 full baths, the layout is ideal for both everyday living and entertaining. Outdoor living is elevated with a rear balcony overlooking the water and a front covered lanai, perfect for enjoying Naples’ spectacular sunsets while grilling outdoors. Additional features include covered parking, a private storage room, and the convenience of a pet-friendly community with low HOA fees. The boutique complex consists of just six residences, offering privacy and a quiet, exclusive atmosphere—minutes to Naples Bay Resort and Marina, 5th Avenue South, 3rd Street South, Tin City, and the city’s world-class shopping, dining, arts and white sandy beaches. Naples Private Airport is just minutes away, making travel to your residence effortless.

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.

Unrivaled Views. Unmatched Lifestyle. Welcome to your dream coastal retreat in the heart of Naples' coveted Oyster Bay, where breathtaking views and refined updates come together in perfect harmony. This beautifully renovated 2-bedroom + den, 2-bathroom condo offers commanding, unobstructed views of Naples Bay from nearly every room — including the living and dining areas and both bedrooms. Perched at the end of a quiet cul-de-sac, this residence offers direct Gulf access and includes a deeded dock, making it ideal for boating enthusiasts and sunset seekers alike. With desirable southern and western exposures, you'll enjoy panoramic water views, golden afternoon light, and unforgettable Naples sunsets — all from the comfort of your own home. Set in a tranquil natural setting, watch dolphins glide, manatees surface, and coastal birds soar — right from your windows or balconies. This is more than a home — it’s a front-row seat to the serene rhythm of life on the water. Inside, you'll find tasteful, modern upgrades including wood-look luxury vinyl flooring throughout, stainless steel KitchenAid appliances, soft-close cabinetry and quartz/quartzite countertops ,recessed lighting and motorized blinds for effortless ambiance and impact-resistant windows and sliders for peace of mind. Both bathrooms have been fully updated with sleek vanities, designer lighting, and spacious walk-in showers. Step outside to enjoy two private balconies, a covered carport, and extra storage. Located in the intimate community of Chesapeake Point, you're just a short walk or bike ride to downtown Fifth Avenue, home to Naples' finest dining, shopping, and cultural attractions. Whether you're seeking a year-round residence or a luxurious seasonal escape, this waterfront gem delivers the ultimate Southwest Florida lifestyle — tranquil, elegant, and endlessly scenic.

Location meets elegance and charm in this incredibly spacious 2 bedroom, 2.5-bathroom, 2 floor condo in highly desirable, Royal Harbor.The entire building has just been freshly painted! Step inside this bright and airy condo featuring a gorgeous balcony with southern exposure overlooking a canal, along with a new 28 foot boat dock and deeded boat slip. Enjoy direct gulf access with no bridges to the bay and numerous waterfront restaurants via boat or car. Entertain inside with an open concept kitchen complete with recessed lighting, tray ceiling, stainless steel appliances, perfectly appointed cabinetry finished off with granite countertops. An abundance of storage awaits in the laundry room adjacent to the kitchen while the main living space showcases the amazing views through picturesque sliders. Escape upstairs to a couple of ensuite bedrooms that boast large walk-in closets, private balconies and an exorbitant amount of space. Cool off in the refreshing newly renovated pool with views of the canal under giant, majestic palms. Just minutes to 5th Ave, downtown Naples, featuring world-class restaurants, shopping, and the pristine beaches of the gulf of Mexico, your permanent vacation awaits!

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!!!

Bring your boat and your toothbrush! This unique waterfront, second floor end unit #109 offers a fully furnished, open floor plan with two screened lanais, two covered parking spaces, and easy boating access to Naples Bay. Features include three bedrooms, two bathrooms, an updated kitchen, 19-inch tile throughout, in-unit laundry, wheelchair accessibility, hurricane impact windows, plantation shutters, new lighting, new ceiling fans, and fresh paint. Conveniently located less than a mile from Tin City and the 5th Avenue restaurants, this charming Sea Eagle community includes 18 units which are hurricane resistant due to the building’s elevated structure. No units have been damaged by any hurricanes. Enjoy the beautiful pool and the spacious covered patio area with your guests and neighbors. Other amenities include an elevator, individual storage lockers, a bicycle storage room, and a conveniently located garbage chute. Sea Eagle is a boater's paradise. Boat slips are available at no additional cost. Enjoy a short boat ride to dinner at The Boat House, The Dock, Celebration… etc. Take a leisurely ride along the intercoastal waterway to Keewaydin Island and Marco Island. Come check out this rare opportunity for yourself

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.