Oyster Bay Real Estate For Sale55+ Active Adult

Oyster Bay contains (25) subdivisions
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Cherrystone Court At Oyster Bay, 1200 Cherrystone Ct #B209, Naples, Florida 34102, image 1
$425,000 $26K
  • 2 Beds
  • 2 Baths
  • 1,276 SqFt
  • $333/SqFt
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Condo for sale in Cherrystone Court At Oyster Bay
1200 Cherrystone Ct #B209, Naples, FL 34102
New deeded boat dock with royal harbor condo for $425k! Amazing price point for this area of town! Condo comes with a brand new 30' deeded boat dock with direct access and no bridges to naples bay! Perfect for a permanent home, a peaceful escape, or use for investment purposes. This is your chance to own in a prime naples neighborhood and wake up to your own peaceful waterfront backyard with your boat parked right below you! Captivating eastern exposure water view from your master bedroom and screened lanai overlooking the tranquil canal as well as a short stroll or bike ride to 5th avenue. This 55+ community offers endless days of serene laid-back living with a community pool and grill area providing the perfect setting for entertaining, and the proximity to the beach and downtown hotspots such as 3rd street, bayfront, and tin city means the best of naples is right at your fingertips. It's time to live a life that truly embodies the naples lifestyle. Do not miss this opportunity!
Blue Point At Oyster Bay, 1686 Blue Point Ave #A1, Naples, Florida 34102, image 1
$389,000 $10K
  • 2 Beds
  • 2 Baths
  • 1,102 SqFt
  • $353/SqFt
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Condo for sale in Blue Point At Oyster Bay
1686 Blue Point Ave #A1, Naples, FL 34102
Investor and boaters dream! Best-priced waterfront condo with dock access in naples! Completely renovated 2br/2ba end-unit in the highly desirable blue point community in oyster bay/royal harbor. Boat slips available to lease for only $300/year with direct dock access steps from the unit—ideal for boaters. This first-floor residence offers a split-bedroom layout, new lpv floors, and a screened enclosed lanai with canal and pool views. Brand new appliances, butcher block countertops, new air conditioner, updated baths, brand-new 2025 seawall (raised ~3 ft), dock, and roof. Assessments paid in full! Low-density, walkable community minutes to olde naples, 5th avenue south, downtown, and gulf beaches. Rental-friendly: up to 12 rentals per year (30-day minimum) with community pool, bbq area, extra storage, and low-maintenance fees including insurance, lawn care, and pest control. Exceptional waterfront investment and boating opportunity!
Chesapeake Landings At Oyster Bay, 1519 Chesapeake Ave #B-5, Naples, Florida 34102, image 1
$429,000 $20K
  • 2 Beds
  • 2 Baths
  • 1,080 SqFt
  • $397/SqFt
Entry-Level
Condo for sale in Chesapeake Landings At Oyster Bay
1519 Chesapeake Ave #B-5, Naples, FL 34102
Discover the privacy of condo living with the rare luxury of direct gulf access from your own dock. This light-filled, fully updated 2-bedroom, 2-bath condominium in the desirable oyster bay neighborhood offers the ideal boater’s lifestyle with northwest exposure and beautiful sunset-glow views down the channel. Modern and inviting, the residence features tile flooring throughout, renovated baths, a tankless water heater, and an updated kitchen with granite countertops and stainless-steel appliances. A notable advantage is the private, full-size washer and dryer inside the unit—a convenience that truly sets this home apart. Offered turnkey with elevated neutral décor, the property is move-in ready for seasonal enjoyment, full-time living, or immediate investment. The community’s 2019 roof provides added peace of mind. Located just minutes from 5th avenue dining, shopping, and naples’ renowned beaches, and only a five-minute boat ride to the city dock, this home delivers exceptional waterfront living at an incredible value. Opportunities like this are rare—come experience why this is the ideal boater’s retreat before it’s gone.

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Escondido Marina At Oyster Bay, 1400 Blue Point Ave #202, Naples, Florida 34102, image 1
$779,000
  • 2 Beds
  • 21/2 Baths
  • 1,960 SqFt
  • $397/SqFt
Entry-Level
Condo for sale in Escondido Marina At Oyster Bay
1400 Blue Point Ave #202, Naples, FL 34102
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.
Granada At Oyster Bay, 1425 Curlew Ave #2-1, Naples, Florida 34102, image 1
$429,900
  • 2 Beds
  • 2 Baths
  • 975 SqFt
  • $441/SqFt
Mid-Tier
Condo for sale in Granada At Oyster Bay
1425 Curlew Ave #2-1, Naples, FL 34102
.This charming, renovated, first-floor, 2-bedroom, 2-bath end-unit condo comes with an assigned boat dock for up to a 25 feet boat, seawall was replaced in 2020. Good for 50 years. Perfect for those seeking a serene escape. The contemporary kitchen features new white cabinetry, sleek quartz countertops, modern cabinet pulls, custom lighting. Updates throughout include impact windows, new a/c system, new roof and modern finishes in the updated master bath. Enjoy endless aquatic adventures with direct access for boating and fishing enthusiasts, right at your doorstep, adding a new dimension to your naples, fl lifestyle. Located close to pristine beaches, renowned downtown restaurants, shopping and adventures available at the nearby naples bay resort and marina.
Cherrystone Court At Oyster Bay, 1200 Cherrystone Ct #A104, Naples, Florida 34102, image 1
$565,000 $76K
  • 2 Beds
  • 2 Baths
  • 1,276 SqFt
  • $443/SqFt
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Condo for sale in Cherrystone Court At Oyster Bay
1200 Cherrystone Ct #A104, Naples, FL 34102
This two-bedroom, two-bathroom condo is professionally remodeled, fully furnished, and stayed high and dry during hurricanes, offering everything you need for your gulf coast living lifestyle. It has undergone a complete transformation, featuring an expanded kitchen, bathrooms, flooring, appliances, and a complete electrical overhaul (new sliding glass doors will be installed soon). The new space features quartz countertops, generous seating, and sophisticated finishes throughout, including wide oak vinyl flooring and large porcelain tiles in the bathrooms. The spacious living area opens to a screened lanai and private patio, offering tranquil views of the water and your new seawall, new wooden deck, and deeded 30-foot boat slip with unrestricted access to the gulf of mexico. Residents enjoy exclusive amenities such as private storage, heated pool, social clubhouse, bbq area, and newly constructed seawall and decking, all within a vibrant 55+ community. This is the perfect time to find your next home in beautiful naples, fl, and still be able to enjoy our award-winning beaches, shopping, and dining just moments away. Whether you’re interested in year-round florida living or want to enjoy a few months out of the winter snow, this gorgeous condo is just right for you.
Chesapeake Manor At Oyster Bay, 1417 Chesapeake Ave #202, Naples, Florida 34102, image 1
$480,000 $32K
  • 2 Beds
  • 2 Baths
  • 1,028 SqFt
  • $467/SqFt
Mid-Tier
Condo for sale in Chesapeake Manor At Oyster Bay
1417 Chesapeake Ave #202, Naples, FL 34102
Deeded 25-ft boat dock included-your direct access to naples bay! This furnished, top floor 2-bedroom, 2-bath contemporary condo sits in a charming two-story, canal front building perfect for boaters and those seeking easy coastal living. Both bedrooms are en-suite, offering comfort and privacy, with the primary suite featuring a walk-in closet. The updated interior includes upgraded appliances, granite countertops in the kitchen and bathrooms, porcelain wood-look flooring, recessed led lighting, impact hurricane windows, stainless steel appliances, and a full -size in unit washer and dryer. Enjoy the heated community pool, dedicated parking space and additional locked private storage. Located in the peaceful, 16-residence chesapeake manor, this condo is in a prime location just over a mile to 5th avenue south and minutes to naples' beaches, shopping and dining. A perfect blend of convenience, comfort and waterfront lifestyle!
Granada At Oyster Bay, 1575 W Curlew Ave #1, Naples, Florida 34102, image 1
$459,000 $26K
  • 2 Beds
  • 2 Baths
  • 975 SqFt
  • $471/SqFt
Mid-Tier
Condo for sale in Granada At Oyster Bay
1575 W Curlew Ave #1, Naples, FL 34102
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.
Clam Court Marina At Oyster Bay, 1195 Clam Ct #202, Naples, Florida 34102, image 1
$420,000
  • 2 Beds
  • 2 Baths
  • 886 SqFt
  • $474/SqFt
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Condo for sale in Clam Court Marina At Oyster Bay
1195 Clam Ct #202, Naples, FL 34102
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
Chesapeake Manor At Oyster Bay, 1417 Chesapeake Ave #104, Naples, Florida 34102, image 1
$439,900 $11K
  • 2 Beds
  • 2 Baths
  • 913 SqFt
  • $482/SqFt
Mid-Tier
Condo for sale in Chesapeake Manor At Oyster Bay
1417 Chesapeake Ave #104, Naples, FL 34102
Enjoy serene royal harbor waterfront living where sparkling canal views, passing boats, and modern design create an exceptional naples coastal retreat just minutes from old naples world-class beaches, shopping and dining. Set along a scenic canal in prestigious royal harbor, this beautifully reimagined residence delivers refined waterfront living with tranquil views and exceptional upgrades. Extensively remodeled, the light-filled interior showcases impact glass windows, fresh paint, and a stunning new kitchen featuring quality cabinetry, stainless appliances and quartz countertops. Porcelain tile flows seamlessly through the residence, complemented by designer light fixtures that enhance the home’s clean, contemporary aesthetic. Renovated baths and thoughtfully curated finishes create a sophisticated, low-maintenance environment for a move-in ready experience. Ideally in a desired corner location closest to the canal, the residence enjoys additional end-unit windows that fill the home with natural light and enhance its bright, airy atmosphere. The thoughtfully designed floor plan includes two spacious bedrooms and two fully renovated baths, with quartz surfaces carried throughout for a cohesive and refined finish. A designated parking space and private storage room provide added convenience, offering ideal space for beach equipment, bicycles and recreational gear. Exterior updates have recently been completed to enhance the property’s appeal as the ultimate coastal retreat. Outdoors, chesapeake manor enjoys a tranquil waterfront setting where an angled canal view creates an ever-changing backdrop of sparkling water and passing boats. The screened, under-roof lanai overlooks the pool and canal, creating a setting for sparkling, sunny afternoons. Residents can watch the boats glide by, fish from the seawall, or relax beside the beautiful sunny pool and lounging deck with umbrellas. The outdoor living space is enhanced by a private courtyard atmosphere and lush landscaping, creating a serene setting for quiet enjoyment and effortless entertaining. Chesapeake manor is a private, low-density waterfront enclave with just 16 residences, offering an intimate coastal lifestyle in one of naples desirable locations. Royal harbor is one of naples desirable waterfront neighborhoods, ideally just minutes from downtown’s renowned 5th avenue south and 3rd street south districts, offering world-class dining, shopping and white sand gulf beaches. Residents enjoy a relaxed coastal lifestyle with boating access, quiet residential streets, and exceptional proximity to naples’ cultural and social amenities. Whether for a weekend retreat for naples residents or travelers from afar, or an exceptional opportunity to enjoy full-time waterfront living, this residence presents a rare opportunity to experience naples lifestyle with the ease, beauty and peace of mind of extensive modern updates.
Chesapeake Landings At Oyster Bay, 1517 Chesapeake Ave #B3, Naples, Florida 34102, image 1
$525,000
  • 2 Beds
  • 2 Baths
  • 1,080 SqFt
  • $486/SqFt
Entry-Level
Condo for sale in Chesapeake Landings At Oyster Bay
1517 Chesapeake Ave #B3, Naples, FL 34102
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, making this an ideal retreat for boating enthusiasts, and the condo is sold turnkey furnished for immediate enjoyment or rental use. Washer and dryer hookups are available, with the option for installation in the future. 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. **this property qualifies for a 1% lender incentive if using preferred lender. Inquire for more details.**
Granada At Oyster Bay, 1595 Curlew Ave #4, Naples, Florida 34102, image 1
$570,000 $25K
  • 2 Beds
  • 2 Baths
  • 975 SqFt
  • $585/SqFt
Mid-Tier
Condo for sale in Granada At Oyster Bay
1595 Curlew Ave #4, Naples, FL 34102
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!
Oyster Bay, 1225 Sandpiper St, Naples, Florida 34112, image 1
$989,000
  • 2 Beds
  • 2 Baths
  • 1,624 SqFt
  • $609/SqFt
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House for sale in Oyster Bay
1225 Sandpiper St, Naples, FL 34112
New metal roof! No hoa fees! Private location 1 mile to downtown! Tucked away on a private street in the royal harbor area. Boat slips available for lease nearby! Beautiful old florida multi-level home with double garage, bonus ground-floor guest/mother-in-law suite with spacious open area, private bath and screened lanai. Spacious and sunny great room design with island kitchen, screened lanai and open deck. The top-quality finishes, open layout and exceptional location near upscale shopping dining and the white sandy gulf beaches make this home the perfect opportunity to live the naples lifestyle.
Granada At Oyster Bay, 1455 Curlew Ave #1, Naples, Florida 34102, image 1
$599,000 $30K
  • 2 Beds
  • 2 Baths
  • 975 SqFt
  • $614/SqFt
Mid-Tier
Condo for sale in Granada At Oyster Bay
1455 Curlew Ave #1, Naples, FL 34102
Dazzling newly renovated coastal gem with designer finishes, perfectly poised in an ideal location, just a mile+ to downtown 5th ave.! Exquisitely rebuilt from floor to ceiling in 2023. Stylish accents include; tile flooring throughout, full wall backsplash, marble style kitchen counters, white cabinetry, spa-like showers, custom wall-to-wall closet in primary bedroom. A boaters delight offering direct access to the gulf from your boat dock! Nearby is fine dining, shopping, dancing, luxury resorts, naples famed white sand beaches! Just a short stroll or scenic bike ride to the marina, tin city, bayfront restaurants or multiple parks. Beach lovers will revel in the coastal lifestyle with year-round florida sunshine and breathtaking sunsets. Investors, opportunity knocks in this coveted 34102 sweet spot. Single story, desirable open concept floor plan with breakfast bar. Laundry area contains full size washer and dryer. 2 assigned parking spaces. New appliances. New impact resistant windows. Slider door from main area leads to the private patio for tranquil living whether outdoors or in. Revel in the quintessential naples lifestyle that many dream of, and don't miss this unique property which has it all!
Granada At Oyster Bay, 1405 Curlew Ave #3, Naples, Florida 34102, image 1
$685,000 $15K
  • 2 Beds
  • 2 Baths
  • 1,100 SqFt
  • $623/SqFt
Mid-Tier
Condo for sale in Granada At Oyster Bay
1405 Curlew Ave #3, Naples, FL 34102
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.
Blue Point At Oyster Bay, 1686 Blue Point Ave #B1, Naples, Florida 34102, image 1
$749,000
  • 2 Beds
  • 2 Baths
  • 1,198 SqFt
  • $625/SqFt
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Condo for sale in Blue Point At Oyster Bay
1686 Blue Point Ave #B1, Naples, FL 34102
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!!!
Blue Point At Oyster Bay, 1686 Blue Point Ave #B5, Naples, Florida 34102, image 1
$775,000
  • 2 Beds
  • 2 Baths
  • 1,198 SqFt
  • $647/SqFt
Premium
Condo for sale in Blue Point At Oyster Bay
1686 Blue Point Ave #B5, Naples, FL 34102
Experience the ultimate naples waterfront lifestyle in this impeccably renovated end-unit condo in oyster bay, where luxury finishes meet effortless boating access. From your own backyard, take just a few steps to your private 25-foot dock, offering quick, no-bridge access to the gulf—ideal for spontaneous sunset cruises or trips to keewaydin island. Located in the intimate, low-density blue point community of just 16 residences, the building features a brand-new roof and allows up to 12 rentals per year, making this an exceptional opportunity for both full-time enjoyment and healthy rental income potential. This desirable end unit offers southern exposure, tranquil canal views, and an unbeatable location just one mile to fifth avenue south and two miles to naples’ pristine white-sand beaches. A brand-new seawall enhances the waterfront setting, while lush, private landscaping creates a serene backyard retreat where dolphins are often seen passing by. The residence has undergone a complete, high-end renovation with no detail overlooked, including updated electrical systems and a new breaker box. The chef’s kitchen features custom-built cabinetry, sleek quartz countertops, under-cabinet lighting, and brand-new lg appliances. The open-concept living area is anchored by a striking custom media wall with quartz accents, remote-controlled undermount lighting, and advanced cable management for a clean, sophisticated aesthetic. As an end unit, the condo is filled with natural light and showcases beautiful water views from multiple vantage points. Additional upgrades include impact-resistant windows and exterior doors for security and energy efficiency, upgraded interior doors and trim, and a newly enclosed, air-conditioned florida room with new windows—perfect for dining, entertaining, or relaxing while overlooking the canal. Further enhancements include a new a/c system, water heater, and furnace; ceiling fans with remote controls in every room; an in-unit washer and dryer; a locked owner’s closet and secured kitchen cabinet for peace of mind; and an outdoor storage shed offering over 60 cubic feet of additional storage. Just steps away, the community pool provides a peaceful setting for relaxation and socializing. Rarely occupied—only two months per year—this residence remains in pristine condition. Opportunities like this in royal harbor and oyster bay are rare, especially ahead of significant nearby development nearing completion. Schedule your private showing today and experience refined waterfront living with unmatched flexibility, location, and lifestyle appeal. One or more photo(s) has been virtually staged, ai generated or rendered.
Curlew Apartments At Oyster Bay, 1351 Curlew Ave #104, Naples, Florida 34102, image 1
$699,999
  • 2 Beds
  • 2 Baths
  • 1,022 SqFt
  • $685/SqFt
High-End
Condo for sale in Curlew Apartments At Oyster Bay
1351 Curlew Ave #104, Naples, FL 34102
Welcome to a rare opportunity where waterfront living, boating, and the vibrant 5th avenue lifestyle converge into one unforgettable naples address. This beautifully remodeled turnkey first-floor condominium delivers the ultimate coastal retreat, complete with your own private boat slip and breathtaking bay views—an ideal haven for boaters, anglers, and luxury-seeking buyers alike. Thoughtfully redesigned with endless upgrades, this elegant 2-bedroom, 2-bath residence features a bright, open-concept layout enhanced by impact-resistant windows and french doors that frame the shimmering water beyond. The interior exudes refined coastal style with solid granite countertops, stainless steel appliances, updated bathrooms, and modern flooring, creating a turnkey living experience that feels both polished and inviting. Whether entertaining guests or enjoying quiet mornings by the water, every detail has been curated for comfort and effortless sophistication. Step outside and embrace true florida resort living. A private dock accommodating boats up to 25 feet places the bay quite literally at your doorstep, with the option to add a lift for added convenience. The community’s sparkling waterfront pool, surrounded by lush tropical landscaping, offers a serene escape after a day on the water. Located just minutes from the world-class dining, shopping, and cultural attractions of naples, this residence pairs tranquil waterfront living with unbeatable walkable access to downtown energy. With a flexible rental policy, pet-friendly environment, and exceptional proximity to naples’ most coveted destinations, this property is equally suited as a primary residence, vacation getaway, or high-performing investment. This is more than a condo—it’s a front-row seat to the southwest florida lifestyle, where sunsets, salt air, and sophistication meet.
Chesapeake Point At Oyster Bay, 1302 Chesapeake Ave #A3, Naples, Florida 34102, image 1
$1,099,000 $100K
  • 2 Beds
  • 2 Baths
  • 1,450 SqFt
  • $758/SqFt
High-End
Condo for sale in Chesapeake Point At Oyster Bay
1302 Chesapeake Ave #A3, Naples, FL 34102
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.
Bayview Estates At Oyster Bay, 1311 Chesapeake Ave #4A, Naples, Florida 34102, image 1
$1,699,000
  • 3 Beds
  • 3 Baths
  • 2,144 SqFt
  • $792/SqFt
High-End
Townhouse for sale in Bayview Estates At Oyster Bay
1311 Chesapeake Ave #4A, Naples, FL 34102
This beautifully renovated naples bay view townhome is tucked at the end of a cul-de-sac in the sought-after royal harbor area, where a private boatslip just beyond the patio accommodates up to a 32-foot vessel and offers quick access to open water. Set within an intimate enclave of just eight residences, the property captures the essence of relaxed waterfront living, complete with captivating bay views and an air-conditioned oversized two-car garage with epoxy flooring. The home offers a refined yet effortless coastal lifestyle, with a community pool, two private patios on different levels, and water views that invite you to watch yachts cruise by and dolphins play in the bay. Inside, more than $315, 000 in upscale renovations elevate the interiors with large rectified porcelain tile throughout, an expanded kitchen with creamy onyx countertops, a walk-in pantry, custom built-ins, and premium glass and stainless appliances, including a miele dishwasher and built-in wall ovens. The great room opens to a screened waterfront patio, while the dining room and wet bar with wine cooler and custom cabinetry create an ideal setting for stylish entertaining. With three spacious bedrooms, elegantly updated baths, direct boating access and a location just minutes from old naples dining, boutique shopping and gulf beaches, this residence is the complete package for luxury waterfront living.
Oyster Bay, 1390 Chesapeake Ave, Naples, Florida 34102, image 1
$1,590,000
  • 3 Beds
  • 2 Baths
  • 1,795 SqFt
  • $886/SqFt
Premium
Condo for sale in Oyster Bay
1390 Chesapeake Ave, Naples, FL 34102
Completely renovated 3 bedroom, 2 bath, turnkey furnished, waterfront condo on naples bay with direct gulf access & 26 ft boat slip. The interior has been completely renovated and never lived in with luxury finishes and elegant arhaus furnishings throughout creating a stylish and functional living space including impact windows and doors. Second floor end unit with additional windows flood the home with natural light and stunning bay views. Outdoor living is elevated with a lanai overlooking the water perfect for enjoying spectacular sunsets from this tranquil setting. This boutique community consists of only 6 residences with low condo fees, offering a private exclusive atmosphere minutes to 5th avenue, 3rd street, the city's world class shopping, dining, arts and white sandy beaches.
Oyster Bay, 1559 Chesapeake Ave, Naples, Florida 34102, image 1
$2,695,000 $200K
  • 3 Beds
  • 31/2 Baths
  • 2,641 SqFt
  • $1,020/SqFt
Premium
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. 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!
Granada At Oyster Bay, 1395 Curlew Ave #1, Naples, Florida 34102, image 1
$1,200,000
  • 2 Beds
  • 2 Baths
  • 1,056 SqFt
  • $1,136/SqFt
Mid-Tier
Condo for sale in Granada At Oyster Bay
1395 Curlew Ave #1, Naples, FL 34102
Stunning turnkey condo with deeded boat slip included. Luxury 2 bedroom home with 2 full bathrooms. New construction 2022. Built to current hurricane requirements. No damage from latest hurricanes, ian, milton and helene. Built up 4 ft elevated foundation, concrete wall from floor to ceiling between units. Hurricane impact windows. Ceramic title throughout home. Kitchen with ge cafe appliances, double oven, custom cabinets with glass doors along top and accent lighting. Tray ceiling in kitchen with breakfast bar. Spacious living and dining room flows into open front foyer. Beautiful natural light streams through the home. Motorized hunter-douglas smart home window treatments. Boating community. Walk from front door right out to your boat docked in slip #1. Access right to the gulf. No bridges. Walking distance to tin city, 5th ave, shopping and restaurants. Minutes to the best of naples by boat, car or water taxi. Schedule your viewing of this amazing property today.
Bayview Estates At Oyster Bay, 1301 Chesapeake Ave #1B, Naples, Florida 34102, image 1
$2,495,000 $50K
  • 3 Beds
  • 3 Baths
  • 1,981 SqFt
  • $1,259/SqFt
High-End
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, 1510 Chesapeake Ave, Naples, Florida 34102, image 1
$4,349,000
  • 3 Beds
  • 31/2 Baths
  • 3,062 SqFt
  • $1,420/SqFt
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House for sale in Oyster Bay
1510 Chesapeake Ave, Naples, FL 34102
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.
Oyster Bay, 1100 Sandpiper St, Naples, Florida 34102, image 1
$6,250,000 $500K
  • 5 Beds
  • 52/2 Baths
  • 3,600 SqFt
  • $1,736/SqFt
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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
Internet Access
Pool
Sidewalk
Storage
Streetlight
Tennis Court(s)
Underground Utility
Barbecue
Bike Storage
Common Laundry
Community Boat Dock
None
Pool
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Storage

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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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