The community of Oyster Bay is situated in Naples. Ideally situated for access to all of the Naples area facilities and advantages available.

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29 listings match your search criteria.
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Active
1085 Sandpiper St   Naples
  • 5Bedrooms
  • 5Bathrooms
  • 4400Sq Ft
  • 2026Year Built
$7,995,000

Experience the ultimate in Naples living with this new contemporary water view home, minutes from Fifth Avenue South, with a deeded boat slip, oversized four-car garage and generous storage. Offered fully furnished with a curated art package and a golf cart included — arrive with a suitcase. Completed in 2026 and never lived in, this three-story…

Active
1510 Chesapeake Ave   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 3062Sq Ft
  • 2002Year Built
$3,899,000

No bridges between your dock and the Gulf. This Oyster Bay home sits on a canal more than 120 feet wide with direct access to Naples Bay and Gordon Pass, and a private Ipe dock with boat lift, water and power. The rear faces south over a screened, heated pool and overflow spa and a…

Active
1420 Jewel Box Ave   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2585Sq Ft
  • 1980Year Built
$3,095,000

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…

Active
1630 Chesapeake Ave   Naples
  • 4Bedrooms
  • 3Bathrooms
  • 2150Sq Ft
  • 1964Year Built
$2,700,000

One or more photo(s) has been virtually staged, AI generated or rendered. Exceptional waterfront opportunity at 1630 Chesapeake Avenue in desirable Oyster Bay, near Royal Harbor. Enjoy southern exposure on a wide, deep-water canal with direct Gulf access and no bridges. The private boat dock accommodates vessels up to about 40 feet, making it…

Active
1400 Blue Point Ave  202 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1960Sq Ft
  • 1980Year Built
$779,000

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…

Active
1435 Blue Point Ave  1435 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1111Sq Ft
  • 1976Year Built
$719,900

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…

Active
1405 Curlew Ave  3 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1100Sq Ft
  • 1970Year Built
$685,000

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,…

Active
1200 Blue Point Ave  A2 Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1213Sq Ft
  • 1980Year Built
$649,000

Welcome to your Waterfront Escape with BOAT DOCK. This beautifully maintained first-floor, 3-bedroom, 2-bathroom turnkey furnished condo offers the perfect blend of comfort, convenience, and coastal living. Step inside to find a bright, open layout with tasteful furnishings throughout, making this home truly move-in ready. This spacious living and dining areas flow seamlessly to a…

Active
1100 Little Neck Ct  F52 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1171Sq Ft
  • 1980Year Built
$619,900

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…

Active
1595 Curlew Ave  4 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 975Sq Ft
  • 1970Year Built
$549,000

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…

Active
1417 Chesapeake Ave  106 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 913Sq Ft
  • 1970Year Built
$449,900

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…

Active
1379 Chesapeake Ave  A4 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1080Sq Ft
  • 1973Year Built
$425,000

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…

Active
1575 Curlew Ave W 1 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 975Sq Ft
  • 1969Year Built
$405,000

A hidden gem with waterfront dock with room for 16 ft boat just over a mile from 5th Ave. Major price reduction of over $50,000 just taken.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…

Active
1517 Chesapeake Ave  B3 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1080Sq Ft
  • 1973Year Built
$399,000

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…

Active
1195 Clam Ct  203 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 800Sq Ft
  • 1970Year Built
$295,000

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…

Active
1100 Sandpiper St   Naples
  • 5Bedrooms
  • 5Bathrooms
  • 3600Sq Ft
  • 2025Year Built
$60,000

Available for seasonal on a 30 day min basis. Brand new 2025 home! Bring all offers Stoff Cooney Modern Masterpiece: A Trophy of Timeless Elegance Located just one mile from Naples’ renowned 5th Avenue and 1.8 miles from pristine Gulf beaches, this architectural marvel boosting sophisticated luxury by star designer Tina Twigger sets a new…

Active
1690 Chesapeake Ave   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 5500Sq Ft
  • 2026Year Built
$35,000

Crafted for those who expect nothing less than exceptional, this brand-new 2026 waterfront residence by Naples Home Builders is a rare offering in the heart of Naples. Perfectly positioned on an expansive corner parcel, the property boasts 80 feet of water frontage with direct, bridge-free access to Naples Bay and the shimmering Gulf of true…

Active
1100 Sandpiper St   Naples
  • 5Bedrooms
  • 5Bathrooms
  • 3600Sq Ft
  • 2025Year Built
$30,000

30K is the annual rate. The seasonal rate is 60K. See MLS 226022129. Brand new 2025 home! Bring all offers Stoff Cooney Modern Masterpiece: A Trophy of Timeless Elegance Located just one mile from Naples’ renowned 5th Avenue and 1.8 miles from pristine Gulf beaches, this architectural marvel boosting sophisticated luxury by star designer Tina…

Active
1312 Chesapeake Ave  B1 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1450Sq Ft
  • 1979Year Built
$20,000

SEASONAL WATERFRONT RENTAL! Experience the Naples lifestyle from this beautifully renovated and furnished first-floor, 2-bedroom + den, 2-bath residence in the intimate waterfront community of Chesapeake Point. Situated directly on Naples Bay, this exceptional property offers spectacular unobstructed bay views, gorgeous sunsets and a private boat dock accommodating up to a 24' boat with direct…

Active
1395 Curlew Ave  4-3 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 975Sq Ft
  • 2022Year Built
$7,000

Available for the 2027 season! Experience effortless waterfront living in this beautifully renovated two-bedroom, two-bath condominium ideally situated along a peaceful Naples canal. Thoughtfully updated with a fresh, contemporary aesthetic, the residence features high-end finishes and a bright, open-concept layout designed for comfortable everyday living and entertaining. The beautifully appointed interior provides an inviting retreat after…

Active
1322 Chesapeake Ave  C3 Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1450Sq Ft
  • 1979Year Built
$7,000

Spend the season overlooking the water in one of Naples' most peaceful and sought-after locations. Tucked away in Chesapeake Point at Oyster Bay, this beautifully updated and turnkey second-floor end-unit condo offers the kind of setting that makes you slow down and enjoy where you are. The moment you walk in, the view of Naples…

Active
1165 Clam Ct  7 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1449Sq Ft
  • 1980Year Built
$5,500

Clam Court Marina with a 30' BOAT DOCK and gulf access nestled in the desirable Royal Harbor area on a quiet cul-de-sac and just minutes away from the downtown area provides easy access to shopping, dining and entertainment. Enjoy nearby hot-spots such as Tin City, Bayfront, 5th Avenue South, Naples Pier, the Gulf, Celebration Park,…

Active
1417 Chesapeake Ave  104 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 913Sq Ft
  • 1968Year Built
$5,250

Welcome to your perfect Naples seasonal escape! Just pack your bags and start enjoying the Southwest Florida lifestyle—this beautifully appointed 2-bedroom, 2-bath waterfront condo in desirable Royal Harbor is completely ready for your stay. Located on the first floor and just steps from the sparkling community pool and waterfront, this bright corner residence has been thoughtfully…

Active
1400 Blue Point Ave  208 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1875Sq Ft
  • 1980Year Built
$5,000

Escape to paradise at Escondido Marina Condos in Naples, Florida, where waterfront living and coastal convenience come together for the perfect seasonal retreat. Ideally located just minutes from Naples’ pristine Gulf beaches, world-class dining, shopping, and the charm of 5th Avenue South and 3rd Street South, this beautifully furnished condo offers an inviting home base…

Active
1120 Little Neck Ct  E40 Naples
  • 3Bedrooms
  • 2Bathrooms
  • 1405Sq Ft
  • 1980Year Built
$3,500

One or more photo(s) has been virtually staged, AI generated or rendered. Ground-floor waterfront condo in the Four Winds community overlooking Naples Bay. Fully renovated and unfurnished with quartz countertops, stainless LG appliances, soft-close shaker cabinets, updated bathrooms, central air, in-unit washer/dryer, private entrance, and no stairs. Community amenities include a heated pool, tennis,…

Active
1165 Clam Ct  7 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1449Sq Ft
  • 1980Year Built
$2,900

Clam Court Marina with a 30' BOAT DOCK and gulf access nestled in the desirable Royal Harbor area on a quiet cul-de-sac and just minutes away from the downtown area provides easy access to shopping, dining and entertainment. Enjoy nearby hot-spots such as Tin City, Bayfront, 5th Avenue South, Naples Pier, the Gulf, Celebration Park,…

Active
1417 Chesapeake Ave  201 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 913Sq Ft
  • 1968Year Built
$2,400

Fabulous location! Just minutes from 5th Ave shopping & restaurants, Tin City, Bayfront, Naples Pier, 3rd street and beautiful Naples beaches. This condo has been remodeled and boasts new flooring, furniture, linens and kitchenware. The unit is bright and cheerful. Enjoy your morning coffee or evening cocktail on the spacious lanai overlooking the pool and…

Active
1555 Blue Point Ave  6 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 950Sq Ft
  • 1973Year Built
$1,895

**2 BED/2 BATH** UNFURNISHED ANNUAL**ROYAL HARBOR**MINUTES TO DOWNTOWN**NO HOA**Spacious 2-Bedroom, 2-Bath Condo! Enjoy the best of Naples living in this spacious 2-bedroom, 2-bath condo in the desirable Royal Harbor area. Conveniently located just minutes from Downtown Naples, Naples Bay Resort, Tin City, and the beautiful beaches of Naples. With an excellent location and no HOA approval process,…

Active
1360 Chesapeake Ave  1372 Naples
  • 1Bedrooms
  • 1Bathrooms
  • 600Sq Ft
  • 1988Year Built
$1,750

Pet friendly unit. This unit has been slightly refreshed. This unit is located in a lovely building on the water in a great boating community. It is situated on a wide canal with access to Naples Bay with beautiful sunsets every evening. There is a kayak provided if one should so desire to…

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