Oyster Bay - Naples, FL

Quick Facts

Price Range
High $200s - Low $2Ms
Home Types
Single-Family, Condos, Attached
Number of Homes
New / Resale
New And Resale Homes
Age Restrictions
Construction Dates
1960 - 2019
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Oyster Bay Overview

Oyster Bay is an active lifestyle community in Naples, Florida, that includes Four Winds at Oyster Bay and Cherrystone Court Condominiums. Some of the resort-style amenities include outdoor pools, patios, and tennis and shuffleboard courts as well as boat docks. Oyster Bay is conveniently located along Naples Bay, giving residents easy access to nearby entertainment.

Homebuyers looking for low-maintenance single-family, attached, and condo homes in Naples, FL will enjoy all that Oyster Bay has to offer. 

Oyster Bay Amenities & Lifestyle

Residents at Oyster Bay will have access to a number of outdoor amenities. Members of the overall community enjoy a boat dock on Naples Bay right outside their door.

Four Winds at Oyster Bay homeowners also have access to a cabana, pool and patio, tennis and shuffleboard courts, and a barbecue area. Cherrystone Court Condominiums additionally has a pool and patio available to residents.

Members of the community enjoy a low-maintenance lifestyle thanks to a homeowners’ association that takes care of common area and exterior maintenance. With more free time, members of the community can explore shared interests or head out on the boat for the day. 

Oyster Bay Homes & Real Estate

Oyster Bay was constructed between 1960 and 2019 and includes single-family, attached, and condo homes.

The single-family homes range from 1,968 to 2,705 square feet with two to four bedrooms, two to three-and-a-half bathrooms, and an attached one- to two-car garage. Features in some homes include upgraded kitchens and bathrooms, walk-in pantries, and private lanais with french doors.

The attached models are about 1,796 square feet, although some homes may be outside this range. The floor plans include three bedrooms and bathrooms as well as uncovered assigned parking.

The condos at Four Winds at Oyster Bay and Cherrystone Court Condominiums range from 975 to 2,498 square feet with two to three bedrooms, one to three-and-a-half bathrooms, and an attached garage or assigned parking. 

Surrounding Area

Oyster Bay is located in Naples, putting residents in easy reach of daily needs and fun opportunities. 

Residents of Oyster Bay are also close to any conveniences they may need, including Bravo Supermarkets, Publix, and Save A Lot. Pharmacy needs can be met at Walgreens and CVS. 

Oyster Bay is also close to several health care providers, including Naples Community Hospital and NCH North Naples Hospital.

When homeowners are looking for entertainment, they can head to 5th Avenue, where they will find plenty of restaurants, cafes, and shops to choose from. Residents of Oyster Bay are also close to museums such as Naples Depot Museum, Naples Train Museum, and Sheldon Fine Art. 

For residents who wish to get outside, there are plenty of parks and greenspaces to choose from. Cambier Park and Rodgers Park are popular with locals, and the River Park Community Center features additional recreational facilities.  

Residents who want to visit other nearby metropolitan areas are in luck. Fort Myers is an hour away, and Miami is about a two-hour drive, providing easy access to everything these cities have to offer. For longer trips, the Southwest Florida International Airport is under an hour away.

Oyster Bay Homes for Sale

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    Oyster Bay Models


    Showing 2 Models with area.floorplan.default_home_size_filter_label for All Collections

    Standard Model - Condominium

    Standard Model - Single-Family

    Oyster Bay Amenities

    Oyster Bay Amenities

    Amenities at Oyster Bay include:

    • Boat Dock
    • Lake with Boat Access

    Four Winds at Oyster Bay Amenities

    Amenities available to residents of Four Winds at Oyster Bay include:

    • Cabana
    • Heated Pool
    • Outdoor Patio
    • Tennis Courts
    • Shuffleboard Courts
    • Barbecue Area

    Cherrystone Court Condominiums Amenities

    Amenities available to residents of Cherrystone Court Condos include:

    • Outdoor Pool
    • Outdoor Patio

    Oyster Bay Clubs, Groups, Activities & Classes

    There are plenty of activities available in Oyster Bay. Here is a sample of some of the clubs, activities and classes offered here.

    • Boating
    • Shuffleboard
    • Tennis

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