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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.
See all our Activities, on the date and time Calendar. Check out our Clubhouse amenities.
Latest News
Animal Food Drive
Posted on Aug 3rd, 2026
August 3rd-17th
Great Island will be hosting an Animal Food Drive over the next two weeks to benefit Plymouth Helping Hands for Animals. Plymouth Helping Hands for Animals is dedicated to ensuring that every pet receives the love, care, and support they deserve.
Updated Waiver Info
Posted on Jul 27th, 2026
NOTE:
Updated waivers have been mailed to all residents. Please drop the completed waivers in the box in front
of the Front Desk.
We have recently updated the wording of our Resident Informed Consent Release and Waiver Agreement. If you have not signed the updated waiver, you will be receiving mail this week which contains the updated waiver to sign and return.
Also enclosed in the mailing is a Resident Contact Information Update Form. As many residents have called Great Island home for a number of years, some of the contact information we have on file may no longer be current. We would appreciate if you could take a few moments to update your information so we can ensure our records are accurate.
For your convenience, a collection box is located in front of the Front Desk where you may drop off both your completed waiver and contact information form.
Please have the waiver returned no later then Monday, August 17th.
Upcoming Events
Jimmy Keys, Musical Comedy Entertainer
Sunday, August 16th
Sunday, August 16th
Doors open 6pm, show starts at 7pm
This high energy evening with Jimmy Keys will be packed with music, singing, comedy and amazing impressions, all wrapped up with fantastic piano playing and screamingly funny humor. Don’t miss this wonderful performer on this very special evening! His last two appearances at Great Island SOLD OUT.
Sign up for your table on Saturday, July 11 AT 8am
$27.00 per person, Checks payable to Great Island Activities Group
On Our Own Sunset Cruise
Monday, August 17th
Pilgrim Belle
August 17th, 6pm
Book and pay online at Captain John. Once you have booked online, sign up on the clipboard at the Overlook Clubhouse to let On Our Own know you will be attending.
Comfort Keeper Sign Up
Tuesday, August 18th
Senior Living & Healthcare Consultations
Tuesday, August 18th
Overlook Clubhouse
Schedule a 15 minute appointment
Sign up at the Clubhouse
No fee
Meet with Ruth McNaughton to discuss questions and concerns regarding geriatric care management, home health services, discharge planning and hospital follow up, navigating health system complexities and coverage options, and staying safely at home for longer.
Email Jessica with any questions.
Complimentary Hearing Screening
Tuesday, August 18th
Tuesday, August 18th
12:30PM-3:30PM
Clubhouse Craft Room
Book an appointment for a complimentary hearing screening, hearing aid cleaning or video ear exam. Sign up on the Clipboard at the Clubhouse.
Email Jessica with any questions.
Email Jessica with any questions.
See flyer for additional information and dates.
