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Welcome to Great Island at the Pinehills! We are a community of 600 homes, specially designed for active adults who are 55 and older. Our website is your one-stop-shop for all things Great Island. Here, you will find information about our neighborhood, clubs, activities, rules and regulations, and the resources available to our residents in our clubhouse.
As part of the larger Pinehills community, our residents have access to a wide range of amenities including miles of walking trails, tennis and bocce courts, exercise rooms, pools, ponds and golf. There are at least a dozen golf courses within a 30-40 minutes drive and two right across the street. All of these are set in an idyllic woodland retreat, making Great Island the perfect place for active adults to call home.
Whether you're a current resident or considering joining our community, our website is the best source of news, information, and resources for the residents of Great Island. Please take the time to explore our website and discover all that Great Island has to offer. If you have any questions please don't hesitate to contact us. We look forward to welcoming you to Great Island.
Latest News
Holiday Toy Drive
Posted on Nov 18th, 2025
Sponsored by the GI Pickleballers
December 1 - December 10
Overlook Clubhouse
Join the Great Island Pickleballers in donating toys to the Plymouth Family Resource Center. Donate new unwrapped toys and new pajamas for Ages 0-17. You can place items on the table in the Clubhouse Living Room starting Monday, December 1.
Help share joy and create a wonderful Holiday Season for local youth on the South Shore.
Upcoming Events
Holiday Walkabout
Thursday, November 13th to Saturday, December 13th
The Great Island Holiday Walkabout has been a tradition for over 20 years. Many residents open their homes for this progressive party with the first two stops having appetizers, and the last stop dessert. It is open to Great Island residents only and will begin at 4:30 on Saturday afternoon, December 13th, ending at 9pm.
Sign-ups are Nov 13th thru the 24th, either via Event Registration on the website or via Clipboard at the Clubhouse (for those who don't wish to have a website registration).
Senior Steps and Oasis Senior Living
Tuesday, December 9th
Signup and come to the Overlook Clubhouse Tuesday, December 9 at 11:00 AM
Learn what a Geriatric Care Manager can do for you and your family. Services include care management, family mediation, life care planning, and medical advocacy. Coffee and pastries will be served.
Learn what a Geriatric Care Manager can do for you and your family. Services include care management, family mediation, life care planning, and medical advocacy. Coffee and pastries will be served.
Second Sunday Supper
Sunday, December 14th
December 14th 5pm | Overlook Clubhouse Ballroom
You are invited to the Second Sunday Supper club on Sunday December 14 at 5 PM in the Ballroom of the Overlook Clubhouse for a meal of Comfort Food!
Join your fellow residents for a tasty meal, friendly conversation and camaraderie. When you sign up, you will be asked to bring either a main dish, salad or dessert, for 6-8 people.
Sign-up for Second Sunday Supper is online on the GI Website under Event Registration. The Clipboard at the Clubhouse has directions how to do this if you have questions.
Complimentary Hearing Screening
Tuesday, December 16th, 12:30PM-3:30PM at Overlook Clubhouse Crafts Room
Book an appointment for a complimentary hearing screening, hearing aid cleaning or video ear exam. Sign up on the Clipboard at the Clubhouse.