Winding Ways - Jackson, NJ

Quick Facts

Price Range
Mid $200s - Mid $300s
Home Types
Number of Homes
New / Resale
Resale Homes Only
Age Restrictions
Construction Dates
1988 - 1997
U.S. Homes
Request Sales Info

Winding Ways Overview

Winding Ways is an age-restricted community in Jackson Township set in Ocean County, New Jersey. This gated community is open to adults aged 55 and better and offers single-family homes on a resale basis. It is comprised of 554 quality-built homes and features a 15,000 square-foot clubhouse as well as a variety of social clubs.

Winding Ways is great for active adults looking to live in a location with land and open spaces around them. Despite the rural setting, grocery shopping is just down the street. In addition, Winding Ways is just minutes away from malls, restaurants, and entertainment. Convenient access to I-195 allows residents an easy commute to Philadelphia or New York. The community also provides a shopping bus service for trips to malls and grocery stores.

Winding Ways Amenities

The 15,000 square-foot clubhouse in Winding Ways holds an abundance of amenities. Residents can spend a quiet morning or afternoon reading in the library or play a friendly game of billiards. There is also a ballroom for social events and several hobby rooms for arts and crafts enthusiasts and card players. A fitness room keeps residents in shape to participate in all that Winding Ways has to offer. Outdoors, residents can play bocce ball, tennis, horseshoes, or shuffleboard. When it is time to relax, they can cool off in the sparkling outdoor pool.

Winding Ways Homes & Real Estate

This 55 and over community was built starting in 1988 and is comprised of 554 single-family homes which range in size from around 1,200 to over 1,800 square feet. Buyers can select from a resale inventory of two or three bedroom ranch-style homes with two to three bathrooms. All residences have one or two-car garages. Many homes in Winding Ways have open floor plans with vaulted ceilings. Other features include patios, storm doors, sprinklers, security systems, dens, and fireplaces. The monthly homeowner s association dues are reasonable, and all residents pay the same amount.

Winding Ways Lifestyle

Winding Ways offers a lifestyle that caters to physically and mentally active adults. This friendly community has a very active social committee and residents participate in clubs such as fitness club, Italian American Club, travel club, music club, red hats society, yiddish heritage club, and cultural club. Residents also have groups for cards, golf, and bocce where neighbors can partake in competitive game sessions on a regular basis. Winding Ways also has a community bus that stops at malls and grocery stores.

Jackson, NJ Area

Winding Ways is located in Ocean County, New Jersey. Jackson is the largest New Jersey Township and used to be a farming community. People who live here will enjoy the rural character of this locale, but Jackson offers much more than just horse farms and historic houses. It is easy to take advantage of major shopping opportunities in the area such as the Jackson Outlets, Toms River Mall, and Freehold Mall, all only minutes away. The surrounding area also has various parks and recreation centers. Golf enthusiasts will find a large selection of public and private golf courses. In addition, the nearby town of Toms River features a charming array of shops and restaurants.

With convenient access to I-195 it is easy for residents to explore the surrounding area and to discover their own favorite entertainment and recreation options. Winding Ways is also centrally located in relation to Philadelphia which is 30 miles to the west and New York City that is approximately 60 miles to the north. Both cities have international airports for convenient long-distance travel. Winding Ways is the perfect active adult community in Southern New Jersey.

Winding Ways Homes for Sale

Showing Filtered Results: 0 Homes for Sale

    Sorry, no listings in this community match your search criteria. Adjust or reset your filters to see available homes.

    Winding Ways Models


    Showing 9 Models with area.floorplan.default_home_size_filter_label for All Collections

    Somerset - Single Family Homes

    Ashley - Single Family Homes

    Belmont - Single Family Homes

    Rosewood - Single Family Homes

    Danbury - Single Family Homes

    Straton - Single Family Homes

    Cornwall - Single Family Homes

    Devon - Single Family Homes

    Hampshire - Single Family Homes

    Winding Ways Amenities

    Amenities at Winding Ways include:

    • Clubhouse - 15,000 Sq. Ft.
    • Fitness Room
    • Arts & Crafts Studio
    • Ballroom
    • Multi-Purpose Room
    • Card Room
    • Hobby & Game Room
    • Billiards
    • Library
    • Outdoor Pool
    • Outdoor Patio
    • 2 Tennis Courts
    • 2 Bocce Ball Courts
    • 4 Shuffleboard Courts
    • Horseshoe Pits
    • Walking & Biking Trails

    Winding Ways Clubs, Groups, Activities & Classes

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

    • Billiards
    • Bingo
    • Bocce
    • Bowling
    • Bridge
    • Canasta
    • Cards
    • Cultural Club
    • Fitness
    • Golf
    • Holiday Parties
    • Horseshoes
    • Italian American Club
    • Mah Jongg
    • Music Club
    • Needlework Group
    • Pinochle
    • Planned Trips
    • Poker
    • Red Hats
    • Rummy
    • Shuffleboard
    • Single's Club
    • Table Tennis
    • Travel Club
    • Yiddish Heritage Club

    Winding Ways Reviews (7)

    Average Rating for this Community
    Date (Recent first)
    Lee M.
    The amenities are lovely and the neighborhood is quiet. The rules are over the top and rarely actually helpful. It is NOT dog friendly. They allow me to own my dog like they’re extending me a favor. There’s no place to run the dog, and they have to be on a short leash even on my own property. This is made much worse by their terrible maintenance of the sidewalks. With all their crazy rules it’s somehow okay for people to let their trees grow to block the sidewalk. They also make zero effort to keep the sidewalks open in the snow. Half the year the sidewalks are useless. With all the money I pay for the facility’s upkeep, that they care so little about our dogs and sidewalks is infuriating.
    July 29, 2021
    Bernie W.
    A very friendly community. Yes, there are rules, or else the community would be a mess..The rules are reasaonable & help to keep "law & order".There is always someone that cannot be happy, if there are rules. Every city, & state has rules..There is a Board of Trustees, that addresses the necessary "needs" to keep us clean & proper..& they do it all on their own time & dedication to keep us "Lookin good" !
    September 3, 2018
    Wonderful, friendly community. I would disagree with the 2 people (note one of the negative reviews was repeated twice). There are rules, but not unreasonable. Enlargement of patios and driveways are permitted within guidelines. There is a desire to maintain green space ... which for me is one of the things that makes the community appealing.
    September 5, 2017
    very strict rules for everything, from patio, to plantings, to placing storage bins to where you can park?
    June 12, 2015
    Watch out very strict with rules. Wanted to extend my patio 2 feet to help my disabled husband have more room for walking with his can. They would not allow !!
    June 10, 2015
    Watch Out very strict with rules for exisitng changest to patio, even with disabled husband. (MS) They would not flex one bit!!
    June 9, 2015
    Susan L.
    Greenbriar WW is a very friendly community with really nice people. We've lived here about 5 years now and have made wonderful friends. We use the clubhouse all the time and are very active in the clubs and activities. It's so nice to be around people our age with common interests. It's the kind of community where you can ask your neighbor for a cup of sugar and yes I have done that when I was making cookies once!
    September 22, 2014

    The information on this page is aggregated from third-party sources and presented as-is for your convenience. It has not been verified or approved by the developer or homeowners association. does not guarantee the accuracy or completeness of information or assume any liability for its use. is not affiliated with the builder, developer, or HOA of any communities displayed on this website. is not affiliated with the developer(s) or homeowners association of Winding Ways. The information you submit is distributed to a Partner Agent, who is a licensed real estate agent. The information regarding Winding Ways has not been verified or approved by the developer or homeowners association. Please verify all information prior to purchasing. is not responsible for any errors regarding the information displayed on this website.