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Oyster Bay Real Estate For Sale55+ Active Adult

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Villas Ensenada At Oyster Bay, 1180 Clam Ct #1, Naples, Florida 34102, image 1
$1,679,000
  • 3 Beds
  • 31/2 Baths
  • 2,107 SqFt
  • $797/SqFt
Villa for sale in Villas Ensenada At Oyster Bay
1180 Clam Ct #1, Naples, FL 34102
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.
Bayview Estates At Oyster Bay, 1311 Chesapeake Ave #4A, Naples, Florida 34102, image 1
$1,749,000 $150K
  • 3 Beds
  • 3 Baths
  • 2,144 SqFt
  • $816/SqFt
Townhouse for sale in Bayview Estates At Oyster Bay
1311 Chesapeake Ave #4A, Naples, FL 34102
This naples bay view townhome checks all the boxes! In the cul-de-sac of the sought-after royal harbor area, this boater's dream is just a moment to open water. Directly beyond the patio is your boatslip, which can accommodate up to a 32 foot vessel. Inside the residence, you're invited to daydream from the many water views, watch the yachts and dolphin cruise by, or sun at the pool shared by this intimate hamlet of eight homes. Be sure to check out the vistas from two patios located on different levels. From the walls inside, this jewel box is adorned with over $315, 000 in renovations to luxury standards. Designer selections include large, rectified porcelain tile (no carpet), creamy onyx stone tops in kitchen, expanded kitchen has walk-in pantry and additional built-in cabinetry. Modern glass and stainless appliances include a miele dishwasher and built-in wall ovens. The great room offers coastal casual elegance, with with a screened patio overlooking bay and canal. The spacious dining room is a place to entertain while guests enjoy the partial bay views. The wet bar is complete with built in wine cooler, custom cabinets, wine cooler and lighting. Three large bedrooms have ample closet storage and modern elegant bathroom finishes. An air-conditioned, oversized two-car garage with epoxy flooring provides additional comfort and storage. All of this luxury is in minutes of old naples world-class dining, boutique shopping and pristine beaches, this is the ultimate expression of luxury waterfront living.
Oyster Bay, 1559 Chesapeake Ave, Naples, Florida 34102, image 1
$2,895,000
  • 3 Beds
  • 31/2 Baths
  • 2,641 SqFt
  • $1,096/SqFt
Villa for sale in Oyster Bay
1559 Chesapeake Ave, Naples, FL 34102
Brilliant modern waterfront corner villa with a private 30-foot boat slip in the highly coveted royal harbor area waterfront enclave of oyster bay, just 1 mile from naples’ world-class dining, shopping, arts, and the sugar-sand beaches of 5th avenue south and old naples. This stylish home offers 2, 641 sf of living space over 2 levels with 3 bedrooms, 3.5 bathrooms, a private 2-car garage, stunning private saltwater pool/spa, and a dock with a deeded 30-foot boat slip directly behind the property, providing quick access to naples bay and the open gulf. Upon entry, the villa exudes light and air with a soaring 25-foot vaulted ceiling and a dramatic wall of impact glass that floods the foyer and living areas with natural light. The centerpiece of the open-concept design is an ultra modern chef’s kitchen with high-gloss cabinetry, an expansive grey quartz island with striking waterfall edges, and white miele appliances including a gas cooktop.The living and dining areas feature 12-foot-6-inch ceilings & flow seamlessly through fully pocketing sliding glass doors to the private outdoor oasis. The outdoor living area offers a resort experience with a private saltwater infinity-edge pool, sun shelf, spa, poolside gas fire feature, and an outdoor kitchen overlooking the canal and boat dock. This is indoor/outdoor living at its best. Heading upstairs, the custom floating staircase is a stunning architectural focal point that features clear-stained cypress wood treads and stainless-steel suspension cables or take the private elevator for effortless access to the second level. Upstairs, an open loft area, ideal as an office or reading nook, leads to the luxurious primary suite with floor-to-ceiling windows, a sleek modern bathroom, and a private sun terrace overlooking the pool, spa, and serene waterway. Each of the three bedrooms features high 10-foot-9-inch ceilings, private balconies, walk-in closets with custom organizers, and en-suite bathrooms appointed with floating vanities, custom mirrors, and open-concept glass showers. Additional features include motorized shades, wide-plank white oak flooring on the second level, large-format tile flooring on the first, wi-fi pool controls, a tankless on-demand hw heater, and impact glass throughout. Built in 2018, this townhome-style condominium is 1 of only 5 exclusive residences within the row at royal harbor, a boutique modern community. Offering both convenience and lifestyle, this walkable and bike-friendly neighborhood is lined with mature oak trees and is known for being incredibly dog friendly, perfect for morning strolls or evening golf cart rides to the beach. Enjoy sunsets & watch the famous fireworks at the naples pier from your boat dock. This rare modern waterfront residence blends contemporary architecture with an unbeatable location and a true naples coastal lifestyle. Don't miss this opportunity to own a unique, impeccably designed home in one of naples’ most desirable boating communities!
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Bayview Estates At Oyster Bay, 1301 Chesapeake Ave #1B, Naples, Florida 34102, image 1
$2,595,000 $50K
  • 3 Beds
  • 3 Baths
  • 1,981 SqFt
  • $1,310/SqFt
Villa for sale in Bayview Estates At Oyster Bay
1301 Chesapeake Ave #1B, Naples, FL 34102
It’s all about the picturesque views of naples bay, looking west to the city docks and naples yacht club at crayton cove. This 3 bedroom 3 bath condo (with rare 2 car garage) will “wow” you with its breathtaking views the minute you walk through the front door! With the bayside of the condo one large bank of windows, you will have an unobstructed view of the passing boats, naples marina and spectacular sunsets. Offered partially furnished in a neutral palette, you’ll enjoy the calming feel of both the interior and all outside your windows. The kitchen offers stainless steel appliances, quartz counter tops and plenty of cabinet space (as well as “the view”). Your primary and a guest suite open up to a balcony where all three, once again, come with, “the view” of the scenic bay. Aside from the views, this townhome is just steps away from its own boat slip that will accommodate up to a 32ft boat, for when you can’t resist a leisurely day (or night) out on the pristine waters of the gulf or a quick trip to the beaches of keewaydin island. Add the private pool area with its tiki hut, pool bath and wet bar, as well as close proximity to the beach and all olde naples has to offer, and you’ve got a winner.
Oyster Bay, 1506 Jewel Box Ave, Naples, Florida 34102, image 1
$3,950,000 $250K
  • 4 Beds
  • 3 Baths
  • 2,777 SqFt
  • $1,422/SqFt
House for sale in Oyster Bay
1506 Jewel Box Ave, Naples, FL 34102
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!
Oyster Bay, 1100 Sandpiper St, Naples, Florida 34102, image 1
$6,500,000 $500K
  • 5 Beds
  • 52/2 Baths
  • 3,600 SqFt
  • $1,806/SqFt
House for sale in Oyster Bay
1100 Sandpiper St, Naples, FL 34102
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.
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Subdivision Amenities
Bike Storage
Car Wash Area
Common Laundry
Community Boat Dock
Community Boat Slip
Community Gulf Boat Access
Fish Cleaning Station
Fishing Pier
Guest Room
Internet Access
Pool
See Remarks
Sidewalk
Storage
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bike Storage
Clubhouse
Common Laundry
Community Boat Dock
Internet Access
None
Pool
Storage
Nearby Subdivisions
Scores
Walk Score®
Car-Dependent. Most errands require a car.
33

100
Transit Score®
Minimal Transit. It is possible to get on a bus.
0

100
Bike Score®
Somewhat Bikeable. Minimal bike infrastructure.
41

100
Sound Score®
Bearable noise.
79

100
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