Oyster Bay Homes with Boat Dock Private Exterior Features

Welcome to Oyster Bay, a hidden gem nestled in the heart of Naples, Florida. This picturesque neighborhood is renowned for its stunning waterfront properties, offering residents the ultimate coastal lifestyle. Imagine waking up to the gentle sound of waves lapping against your private boat dock, with direct access to the beautiful Gulf of Mexico just moments away.

Oyster Bay boasts a unique blend of serene living and vibrant community spirit. The lush, tropical landscaping and tree-lined streets create an inviting atmosphere, perfect for evening strolls or morning jogs. Residents enjoy a close-knit community, where neighbors become friends, and local events foster a sense of belonging. With its proximity to Naples’ upscale shopping, fine dining, and cultural attractions, Oyster Bay truly offers the best of both worlds.

The homes in this exclusive neighborhood are nothing short of spectacular. Many feature private exterior amenities, including spacious outdoor living areas, lush gardens, and, of course, private boat docks. Whether you’re an avid boater or simply enjoy the tranquility of waterfront living, these homes provide the ideal sanctuary. Picture yourself hosting sunset gatherings on your dock, or embarking on spontaneous boating adventures right from your backyard.

With its prime location, luxurious amenities, and a welcoming community, Oyster Bay is more than just a neighborhood; it’s a lifestyle. Discover the charm and elegance of this waterfront haven and experience the unparalleled beauty and excitement that Naples has to offer. Your dream home awaits in Oyster Bay!

Newest Oyster Bay Homes with Boat Dock Private Exterior Features

$3,395,000

3 Beds ⋅ 3 Baths ⋅ 226018001 MLS

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 ⋅ 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

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

$779,000

2 Beds ⋅ 2.5 Baths ⋅ 226008835 MLS ⋅ Escondido Marina 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

$459,000

2 Beds ⋅ 2 Baths ⋅ 226003015 MLS ⋅ 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

$7,777,000

5 Beds ⋅ 6.5 Baths ⋅ 225065690 MLS

Winner of the 2025 Sand Dollar award for Product Design of the Year for Single Family. Welcome to a visionary newly built 2025 contemporary trophy where Architectural Art Meets Waterfront Living. At 1100 Sandpiper design, nature, outdoor living, and technology converge in to timeless elegance. Just one mile from iconic 5th Avenue South and 1.8 miles from the Gulf Beaches, this modern waterfront marvel fuses bold architectural artistry with effortless indoor-outdoor living. With nearly 200 feet of direct Oyster Bay corner frontage, a 60-foot dock already in place (with room for more), and a sculptural form that commands attention from every angle, this is Naples’ ultimate statement home. Rooted in the five natural elements: water, air, earth, fire, and stone -the residence exists in perfect harmony with its environment. Water shimmers from every perspective. Bright light and air drifts through vast glass walls and open terraces. Earth blooms in the lush rooftop lawn and tropical gardens. Fire glows through eight fireplaces across the home. Over 7,500 square feet of natural stone, including 40+ full marble slabs, anchors the structure in enduring sophistication. Outdoor living rivals the interior with nearly equal finished square footage: fully screened waterfront lounges, sunrise and sunset terraces, and secluded open-air zones. The newly completed 1,500-square-foot rooftop sanctuary - complete with sunrise and sunset lounges framed by glass railings—creates a sky-level retreat beyond compare. Inside, nearly 4,000 square feet under air offer five bedrooms, five full baths and two custom half baths. Dual maste suites: one on each level - serve as spa-like havens with luxurious en suites and double vanities as well as a steam shower. 1500 square-foot wraparound terrace seamlessly merges the main living space with the outdoors. Nicknamed The Modern Taj Mahal designed by reendowed Stoff Cooney, this home’s gallery-like glass architecture and structural integrity are unmatched. Built with solid stainless-steel engineered commercial flood panels, it stands among Naples’ most resilient and forward-thinking waterfront builds. Sustainability and innovation shine through a high-output solar roof system with Tesla Powerwalls, a 30+ speaker high-fidelity audio network, and eight fireplaces, including a dramatic centerpiece framing the 12×14 hot tub. The grounds evoke a private resort—three poolside fire bowls, six sculptural water features, and 25+ rare exotic palms illuminated by 100+ warm custom landscape lights. This is far more than a luxury residence: it’s a living masterpiece where art, nature, and modern engineering coexist in perfect balance. Quite simply, Naples’ most visionary home with unprecedented levels of modern luxury & technology in every detail.

1100 Sandpiper ST, Naples

$685,000

2 Beds ⋅ 2 Baths ⋅ 225019016 MLS ⋅ Granada BLDG.

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.

1405 Curlew AVE Unit 3, Naples

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