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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33 listings match your search criteria.
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Active
1100 Sandpiper St   Naples
  • 5Bedrooms
  • 5Bathrooms
  • 3600Sq Ft
  • 2025Year Built
$7,777,000

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
$3,999,000

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
1435 Blue Point Ave  1435 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1111Sq Ft
  • 1976Year Built
$749,900

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
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
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
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
1537 Chesapeake Ave  A-4 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1080Sq Ft
  • 1973Year Built
$439,900

Beautiful Waterfront condo completely remodeled and ideally situated on the Bay, offering Gulf access with no bridges. This stunning 2/2-unit features high-end appliances, an in-unit washer and dryer, hurricane impact windows and doors, and breathtaking water views. Located just 5 minutes from downtown 5th Avenue, you'll enjoy world-class dining, shopping, entertainment, and Naples white sand…

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
$399,900

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
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
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
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
1495 Blue Point Ave  C Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1529Sq Ft
  • 1990Year Built
$12,000

Gorgeous waterfront condo just a short bike ride from downtown Naples, white sandy beaches, and the area’s fine dining and shopping. Located in Royal Harbor, a sought-after waterfront and boating community, this beautifully updated two-story townhome offers a private tropical setting with a brick-paver patio, firepit, and a waterfront walkway leading to a brand-new boat…

Active
1666 Osprey Ave  203 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1200Sq Ft
  • 1975Year Built
$7,000

Professionally designed with uncompromising quality, this two bedroom two bath condominium is available for off seasonal rental from May 2026 until November 15, 2026 at $3750 per month. January thru April 2027 at $7000 a month. The soothing color palette is reminiscent of the sandy beaches and the sea. Lots of natural light fills…

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

Available for 2027 season!! This meticulously renovated two-bedroom, two-bathroom condominium offers an unparalleled opportunity to experience luxurious waterfront living in the heart of Naples. Nestled on the serene Naples canal, the residence provides immediate access to boating and water activities, while remaining a short distance from the cultural and culinary delights of downtown. The condo…

Active
1165 Clam Ct  7 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1449Sq Ft
  • 1980Year Built
$5,900

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
1120 Sandpiper St   Naples
  • 3Bedrooms
  • 3Bathrooms
  • 2400Sq Ft
  • 1970Year Built
$5,500

Direct access waterfront property.

Active
1360 Chesapeake Ave   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1200Sq Ft
  • 1988Year Built
$4,500

This unit faces the canal with lovely water views. Dock space is available for an additional charge. Stunning views, two-level unit facing the canal with two separate sitting areas on the second floor. One faces the canal and the other faces west towards Naples Bay. Kitchen and great room are on the first…

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
1400 Blue Point Ave  104 Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1550Sq Ft
  • 1980Year Built
$2,900

One of the finest waterfront residences in the area, offering breathtaking water views the moment you walk through the door. Located in a highly desirable waterfront community in Naples, this beautifully updated unit features an open and spacious floor plan designed for effortless coastal living. The modern kitchen and renovated bathrooms blend style and functionality,…

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
1605 Chesapeake Ave  2 Naples
  • 2Bedrooms
  • 1Bathrooms
  • 850Sq Ft
  • 1967Year Built
$2,300

Available March 1 for annual rental. Stunning, renovated, updated, unfurnished unit in a building on a canal. Lovely outdoor deck facing the canal for common use to entertain and relax. Dock is available to launch kayak or paddle board if so desired. High-end finishes throughout the unit with marble…

Active
1186 Cherrystone Ct   Naples
  • 2Bedrooms
  • 2Bathrooms
  • 1163Sq Ft
  • 1983Year Built
$1,795

**ROYAL HARBOR**2 BED 2 BATH ANNUAL**GULF ACCESS**Bring your kayak and paddle board - the Gulf is right at your back door! This 2 bed 2 bath unit in Royal Harbor is light and bright with plenty of room on a quiet, peaceful street. Nearby is Naples Bay Resort, Cove Yacht Club, and downtown shopping. Go to the…

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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