Oyster Bay Homes with Boating Community Type

Oyster Bay Homes with Boating Community Type

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida. This vibrant neighborhood seamlessly blends the charm of coastal living with the conveniences of modern amenities, making it an ideal destination for families, retirees, and boating enthusiasts alike. With its picturesque waterways and lush landscapes, Oyster Bay offers a serene escape while remaining just minutes away from the bustling energy of downtown Naples.

One of the standout features of Oyster Bay is its unique boating community. Here, residents enjoy direct access to the stunning Gulf of Mexico, making it a paradise for those who love to sail, fish, or simply soak up the sun on their private boats. The community is designed with boaters in mind, featuring numerous docks and navigable waterways that enhance the overall lifestyle. Imagine waking up to the gentle sound of waves lapping against your dock, ready to embark on a day of adventure or relaxation.

The homes in Oyster Bay are as diverse as its residents, ranging from elegant waterfront estates to charming single-family homes, each exuding its own unique character. Many properties boast stunning views of the water, expansive outdoor spaces, and luxurious amenities that cater to a laid-back yet sophisticated lifestyle.

Beyond the allure of boating, Oyster Bay is conveniently located near Naples' renowned beaches, upscale shopping, and gourmet dining options. The community is also surrounded by lush parks and nature preserves, providing ample opportunities for outdoor activities and family fun.

Discover the enchanting lifestyle that awaits you in Oyster Bay, where every day feels like a vacation in paradise. Your dream home by the water is just a visit away!

Newest Oyster Bay Homes with Boating Community Type

$749,900
2 Beds ⋅ 2 Baths ⋅ 226025599 MLS ⋅ ACTIVE Status ⋅ Oyster Bay Manor 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
$439,900
2 Beds ⋅ 2 Baths ⋅ 226023946 MLS ⋅ ACTIVE Status ⋅ Chesapeake Landings BLDG.
Beautiful Waterfront condo completely remodeled and ideally situated on the Bay, offering Gulf access with no bridges. This stunning 2/2-unit features high-end appliances, an in-unit washer and dryer, hurricane impact windows and doors, and breathtaking water views. Located just 5 minutes from downtown 5th Avenue, you'll enjoy world-class dining, shopping, entertainment, and Naples white sand beaches. An exceptional opportunity to experience the ultimate Southwest Florida waterfront lifestyle.

1537 Chesapeake AVE Unit A-4, Naples
$400,000
2 Beds ⋅ 2 Baths ⋅ 226021302 MLS ⋅ ACTIVE Status ⋅ Cherrystone Court 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
$425,000
2 Beds ⋅ 2 Baths ⋅ 226018784 MLS ⋅ ACTIVE Status ⋅ Casa Granada 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
$3,395,000
3 Beds ⋅ 3 Baths ⋅ 226018001 MLS ⋅ ACTIVE Status
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.

1420 Jewel Box AVE, Naples
$649,900
2 Beds ⋅ 2 Baths ⋅ 226016825 MLS ⋅ ACTIVE Status ⋅ Four Winds 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
$3,999,000
3 Beds ⋅ 3.5 Baths ⋅ 226013587 MLS ⋅ ACTIVE Status
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
$399,900
2 Beds ⋅ 2 Baths ⋅ 226012606 MLS ⋅ ACTIVE Status ⋅ Clam Court BLDG.
Experience boutique waterfront living in this rare 6-unit condo association, perfectly situated in the heart of Naples. Just minutes from the world-famous 5th Avenue shops and dining—and a short stroll to Naples’ white sandy beaches—this residence blends charm, convenience, and coastal lifestyle. Enjoy tranquil canal views and direct Gulf access with no bridges—a true boater’s paradise. Inside, the light-filled layout is designed for comfort and ease, offering the perfect retreat after a day on the water or exploring downtown . With a rental policy allowing 12 rentals per year, this property is also an ideal opportunity for investors or AirBnB hosts , offering both personal enjoyment and strong income potential

1195 Clam CT Unit 202, Naples
$995,000
2 Beds ⋅ 2 Baths ⋅ 226008397 MLS ⋅ ACTIVE Status ⋅ Chesapeake Point 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
$570,000
2 Beds ⋅ 2 Baths ⋅ 226004747 MLS ⋅ ACTIVE Status ⋅ Granada BLDG.
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!

1595 Curlew AVE Unit 4, Naples
$459,000
2 Beds ⋅ 2 Baths ⋅ 226003015 MLS ⋅ ACTIVE Status ⋅ Granada BLDG.
A hidden gem with waterfront dock with room for small 16 ft boat just over a mile from 5th Ave.This totally renovated unit, 1 story condo corner unit lives as as a private home.Walk into an open foyer that could be a breakfast area, wine bar, or work space area. The white tiles throughout are absolutely stunning.The new Kitchen is open with new LG Appliances, a pot filler over stove and gold accents on white cabinets and beautiful backsplash.The New open floor plan is wonderful for dining and living areas to relax or entertain. Walk onto private lanai which is total screened, an extension of your home it can be used for barbecuing, or entertaining. Enjoy a morning coffee, sip a glass of wine, enjoy a meal or sun bathe in the Florida sun. The new impact windows stream sun into the two bedrooms 2baths to complete your home which is ready for you to decorate and make your own. There is a dock with access to the gulf. It has an electro boat lift running water and a fish cleaning station for your convince. Walk to Naples Bay Resort , Tin City, and Fifth Ave with world class shopping and dining with over 25 restaurants. The beach is a stroll down 5th Ave with its famous sugar sand and tranquil waters. Explore all that Naples has of offer to your wonderful place to call home.

1575 Curlew AVE W Unit 1, Naples
$399,000
2 Beds ⋅ 2 Baths ⋅ 225071695 MLS ⋅ ACTIVE Status ⋅ Chesapeake Landings BLDG.
RENOVATED WATERFRONT CONDO – DIRECT GULF ACCESS – TURNKEY FURNISHED! Nestled on a picturesque street lined with majestic banyan trees, this fully renovated two-bedroom, two-bath residence offers modern luxury in the heart of Naples. The open-concept layout showcases brand-new finishes throughout, including 42-inch cabinetry, sleek flooring, and stylish contemporary details that create a bright, coastal feel. An oversized screened lanai overlooks a wide, tranquil canal—perfect for relaxing while watching boats pass by—with direct, no-bridge access to Naples Bay and the Gulf of Mexico. Each unit includes its own private dock slip, with boat dockage permitted for vessels up to 22 feet, making this an ideal retreat for boating enthusiasts who want quick and convenient access to open water. The condo is being sold turnkey furnished for immediate enjoyment or rental use. Washer and dryer hookups are available, with the option for future installation. Just a short stroll to iconic 5th Avenue South, you'll be immersed in Naples' vibrant downtown lifestyle with world-class dining, shopping, galleries, and entertainment at your fingertips. This prime waterfront setting combines the charm of Old Naples with unmatched boating access, making it an exceptional opportunity for a seasonal getaway, investment property, or personal coastal retreat in one of the city's most sought-after locations. Currently 3 Rental Inquiries for Jan, Feb, March, 2027, from $6800 - $8000 per month **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

1517 Chesapeake AVE Unit B3, Naples
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