Hopkinton (508) 435-6444   •   Holliston (508) 429-2391


Check your settings when you are happy with your print preview press the print icon below.

Show Obituaries Show Guestbook Show Photos QR Code Print

Rollyn Sean Winters

January 5, 1968 - July 10, 2023

Private funeral services

Share your Memorial with Family & Friends

Subscribe to updates for Rollyn Winters

Please choose your subscription settings below, you can unsubscribe through email at any time.

Email me when someone posts in the guestbook

Email me when an update is made to the obituary

Email me on the anniversary of passing


Rollyn Sean Winters, 55, of Holliston, passed away unexpectedly at his home on Monday, July 10, 2023. Born in Plainfield, New Jersey, he was the son of Judith (Miller) Winters and the late R. Arthur Winters.

A 1986 graduate of Holliston High School, Sean earned his Master’s Degree from Montclair State University in New Jersey and was an Elementary School Art teacher in Waltham. He was an accomplished artist and a thoughtful, innovative educator. Sean was a trivia buff and loved watching Jeopardy. He also enjoyed classic TV and music of the ‘50s and ‘60s, loved dogs, and was an avid collector of guitars. Sean was an old soul who will be greatly missed.

Besides his mother, he is survived by his sister, Lora Hunt, and her husband, James, and his brother, K. Brett Winters of Holliston. He also leaves behind his nephews and niece, Corey Hunt of Keene, NH, Shane Hunt of San Francisco, CA, and Kelly Sanderson of Sellersville, PA.

Funeral services are private and are under the care of Chesmore Funeral Home of Holliston. In lieu of flowers, donations may be made to St. Jude’s Children’s Research Hospital.