Gloucester - Gloucester - Judith Ann Diamond, 89, of Gloucester, passed away peacefully on Wednesday, June 18, 2025, in Gloucester, at Seacoast Nursing Home.

She was born on April 23, 1936 in Boston, Massachusetts to Florence M. and Walter R. Milley. She is survived by two daughters Kerry Diamond Guglielmi, Nancy Diamond and her sister Dr. Jane Milley and six grandchildren. She was predeceased by her husband Attorney Joseph Wine who passed away in July of 1997. They lived for many years in Braintree, Massachusetts and after her husband passed she moved to Gloucester, MA to be closer to her daughter Kerry.

She lived a full and productive professional life as a Manager for New England Telephone Company and then as Director of Human Resources for the town of Braintree, MA. She was well known by her friends for hosting many gatherings especially at her Gloucester home that looked out over the harbor.

We will miss her jovial personality, love of life and especially the many happy times we all spent together with Judy and her friends.

A visiting hour will be held in the Greely Funeral Home, 212 Wahington Street, Gloucester, on Tuesday, June 24, from 10 to 11 a.m. followed by a Service at 11 a.m. She will be buried next to her husband in the historic Plain Street Cemetery, 225 Plain Street in Braintree, MA. Relatives and friends are invited to attend. For online condolences, please visit www.greelyfuneralhome.com.