Oyster Bay Real Estate

Oyster Bay Real Estate

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida. This exclusive waterfront community offers the perfect blend of luxury living and natural beauty, making it an ideal place to call home.

Situated in Collier County, Oyster Bay is renowned for its picturesque views of the bay and easy access to the Gulf of Mexico. Residents can enjoy boating, fishing, and other water activities right from their doorstep. The lush landscaping and serene atmosphere create a peaceful oasis for those seeking a tranquil lifestyle.

Oyster Bay features a variety of upscale homes, ranging from spacious waterfront estates to elegant condominiums. With top-notch amenities such as a marina, tennis courts, and a clubhouse, residents can experience resort-style living every day.

Conveniently located near downtown Naples, Oyster Bay offers easy access to fine dining, shopping, and entertainment options. Whether you prefer a relaxing day at the beach or exploring the vibrant cultural scene, Oyster Bay provides the perfect backdrop for a fulfilling lifestyle.

Don't miss the opportunity to experience the beauty and luxury of Oyster Bay. Discover your dream home in this exclusive waterfront community and start living the life you've always imagined.

Newest Listings in Oyster Bay

2 Beds ⋅ 2 Baths ⋅ 226034433 MLS ⋅ Oyster Bay BLDG.

Naples Coastal Living in Desirable 34102! This beautifully refreshed 2-bedroom, 2-full-bath condominium features a bedroom suite for added privacy, newly painted interiors, and new ceiling fans. Enjoy convenient access to the community boat lift and the boating lifestyle Naples is known for. Ideally located in sought-after 34102, close to beaches, waterfront dining, shopping, and downtown Naples.

1195 Clam Ct Unit 203, Naples

3 Beds ⋅ 3 Baths ⋅ 226034349 MLS ⋅ Oyster Bay BLDG.

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

5 Beds ⋅ 5.5 Baths ⋅ 226032953 MLS ⋅ Oyster Bay BLDG.

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 Beds ⋅ 2 Baths ⋅ 226030870 MLS ⋅ Oyster Bay BLDG.

MUST-SEE FULLY REMODELED WATERFRONT HOME — DESIGNED TO THE MAX! 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 St, Naples

2 Beds ⋅ 2 Baths ⋅ 226026545 MLS ⋅ Oyster Bay BLDG.

Experience the best of Naples waterfront living in this beautifully remodeled residence in the prestigious Royal Harbor community. Offering tranquil canal views, passing boats, and a bright contemporary design. This exceptional coastal retreat is just minutes from the white-sand Gulf beaches, world-class dining, and boutique shopping of Old Naples. Extensively remodeled throughout, this move-in-ready home features impact-resistant windows, fresh interior paint, porcelain tile flooring, and a stunning new kitchen with updated cabinetry, quartz countertops, and stainless-steel appliances. Both bathrooms have been completely renovated with elegant finishes. Ideally positioned on a desirable Chesapeake Manor the thoughtfully designed floor plan offers two spacious bedrooms, two beautifully updated bathrooms, a designated parking space, and a private storage room. Chesapeake Manor is an intimate, low-density waterfront community with only 16 residences, offering privacy, charm, and a relaxed coastal lifestyle. Located in one of Naples' most sought-after waterfront neighborhoods, Royal Harbor provides quick access to boating, downtown Naples. Whether you're searching for a full-time waterfront residence, a seasonal getaway, or an exceptional investment opportunity, this beautifully updated home offers the perfect combination of luxury, location, and carefree coastal living.

1417 Chesapeake Ave Unit 106, Naples

2 Beds ⋅ 2 Baths ⋅ 226025599 MLS ⋅ Oyster Bay BLDG.

Experience the ultimate Naples lifestyle from this beautifully positioned two-bedroom, two-bath waterfront condominium offering deep-water direct Gulf access and your own private boat dock with lift, perfect for boating enthusiasts eager to explore Naples Bay, the Gulf and the area's pristine waterways. On the second floor, this light-filled residence enjoys an elevated setting with tranquil canal and marina views from the spacious screened lanai, creating the ideal place to relax with your morning coffee or unwind after a day on the water. A rare and desirable feature, the property also includes a dedicated detached garage, providing secure parking and additional storage. Ideally located just moments from the heart of downtown Naples, you'll enjoy easy access to the world-renowned dining, boutique shopping and vibrant galleries along Fifth Avenue South, as well as the sugar-white sands and breathtaking sunsets of Naples Beach. Whether you're searching for a seasonal retreat, a year-round residence, or an exceptional waterfront investment, this property offers the perfect combination of location, boating lifestyle and best of coastal Naples living.

1435 Blue Point Ave Unit 1435, Naples

2 Beds ⋅ 2 Baths ⋅ 226021302 MLS ⋅ Oyster Bay BLDG.

Strategically located end-unit waterfront condo with extra windows, canal views, and an incredible boating setup in Naples. This charming first-floor 2-bedroom, 2-bath residence includes a brand-new deeded 30-foot boat dock with electric and water, plus a new wooden dock and seawall. Enjoy direct Gulf access with no bridges through Naples Bay, making this a rare opportunity at this price point. Inside, the condo features fresh paint, granite countertops, stainless steel appliances, and inviting living space with peaceful views of the canal and boat dock. The end-unit location adds extra natural light and a more open feel. The residence is comfortable as-is while also offering the opportunity to personalize and update over time to create your ideal Naples waterfront retreat. Cherrystone Court is a 55+ community offering a community pool and BBQ/grill area in a relaxed waterfront setting. Ideally located near Royal Harbor, Naples Bay, Tin City, Bayfront, 5th Avenue, 3rd Street, dining, shopping, beaches, and all the best of the Naples lifestyle. Whether used as a permanent residence, seasonal escape, or investment opportunity, this is a rare chance to own a waterfront condo with a private deeded dock and no-bridge Gulf access in one of Naples’ most desirable boating locations.

1200 Cherrystone Ct Unit B108, Naples

2 Beds ⋅ 2 Baths ⋅ 226018784 MLS ⋅ Oyster Bay BLDG.

One or more photo(s) has been virtually staged, AI generated or rendered. Experience exceptional waterfront living in this fully renovated condominium offering direct Gulf access and panoramic canal views. Completely rebuilt from the studs during an extensive 2025/2026 renovation, this highly sought-after residence combines modern luxury with premier boating convenience in the heart of Naples. The open-concept floor plan features wide-plank luxury vinyl flooring, LED recessed lighting, and impact-resistant sliders, windows, and front door throughout. The chef’s kitchen serves as the centerpiece of the home with quartz countertops, custom white shaker cabinetry, an oversized island, and stainless steel appliances. The spacious living and dining areas flow seamlessly to a private screened lanai with desirable southern exposure, providing abundant natural light and peaceful views of the deeded boat docks and navigable canal. Enjoy immediate deep-water, no-bridge access to the Gulf directly from your residence. Both the primary and guest suites feature upgraded en-suite bathrooms with frameless glass showers and thoughtful cross-ventilation design. This is not a cosmetic renovation. Major upgrades include new electrical, plumbing, air ducts, walls, bathrooms, flooring, lighting, foundation improvements, water main, and additional substantial interior system updates. Ideal for boating enthusiasts, seasonal residents, or investors seeking a waterfront property just minutes from Fifth Avenue South shopping, dining, and Naples’ world-famous beaches.

1379 Chesapeake Ave Unit A4, Naples

2 Beds ⋅ 2 Baths ⋅ 226016825 MLS ⋅ Oyster Bay BLDG.

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.

1100 Little Neck Ct Unit F52, Naples

3 Beds ⋅ 3.5 Baths ⋅ 226013587 MLS ⋅ Oyster Bay BLDG.

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

2 Beds ⋅ 2.5 Baths ⋅ 226008835 MLS ⋅ Oyster Bay BLDG.

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.

1400 Blue Point Ave Unit 202, Naples

2 Beds ⋅ 2 Baths ⋅ 226008397 MLS ⋅ Oyster Bay BLDG.

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.

1302 Chesapeake Ave Unit A3, Naples

Start Your Search