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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20 listings match your search criteria.
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Active
1690 Chesapeake Ave   Naples
  • 4Bedrooms
  • 4Bathrooms
  • 5500Sq Ft
  • 2026Year Built
$8,900,000

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
$7,000,000

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…

Active
1510 Chesapeake Ave   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 3062Sq Ft
  • 2002Year Built
$4,349,000

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…

Active
1420 Jewel Box Ave   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2585Sq Ft
  • 1980Year Built
$3,395,000

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-…

Active
1302 Chesapeake Ave  A3 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1450Sq Ft
  • 1979Year Built
$1,099,000

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…

Active
1225 Sandpiper St   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1624Sq Ft
  • 1984Year Built
$989,000

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…

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
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
1100 Little Neck Ct  F52 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1171Sq Ft
  • 1980Year Built
$649,900

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

Welcome to your Waterfront Escape with BOAT LIFT - this beautifully maintained first-floor, 3-bedroom, 2-bathroom 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…

Active
1595 Curlew Ave  4 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 975Sq Ft
  • 1970Year Built
$570,000

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  202 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1028Sq Ft
  • 1968Year Built
$480,000

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…

Active
1575 Curlew Ave W 1 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 975Sq Ft
  • 1969Year Built
$459,000

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…

Active
1425 Curlew Ave  2-1 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 975Sq Ft
  • 1970Year Built
$429,900

.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…

Active
1200 Cherrystone Ct  B108 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1100Sq Ft
  • 1975Year Built
$425,000

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…

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
1200 Cherrystone Ct  B209 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1276Sq Ft
  • 1974Year Built
$425,000

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…

Active
1195 Clam Ct  202 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 886Sq Ft
  • 1970Year Built
$420,000

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.…

Active
1200 Cherrystone Ct  B-109 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1396Sq Ft
  • 1974Year Built
$399,000

An exceptional boating opportunity in Naples at an incredible value! Waterfront living meets direct Gulf access in this charming first-floor residence at Cherrystone Court, complete with a deeded 30-foot boat dock featuring electric & water, a new wooden dock and seawall, and NO BRIDGES to the Gulf — offering the effortless boating lifestyle so many…

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…

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