Diane E. (Rae) Crowley, age 75, a longtime resident of Winchester, passed away on September 9, 2026, lovingly surrounded by her family, after a 50-year battle with multiple sclerosis and several bouts of cancer. She was the beloved wife for 55 years of Larry Crowley.

Born in Woburn, MA, Diane was the daughter of the late James R. and Norma G. (Boyle) Rae. She was raised and educated in Winchester and was a graduate of Winchester High School with the class of 1969.

Diane worked at Houghton-Mifflin Publishing Company for many years and was a bank teller at Winchester Savings Bank, where she was a recognizable face.

In her spare time, Diane enjoyed baking and cooking and was famous for her cookies and “Auntie Di’s blonde brownies” which family members eagerly awaited at Christmastime. She also enjoyed reading and spending time with family and friends.

In addition to her husband, Larry, Diane is survived by her sons: Stephen J. Crowley, of Newport, NH and Shawn M. Crowley of Winchester. She was the dear sister of Robert Rae and his wife Jean of Johnstown, PA, Millie Ruzzo of Yucca Valley, Ca, Carolyn Slack and her husband Paul of Woburn, Maggie Gilpatrick of Derry, NH, Colleen Lisacki and her husband Tony of Methuen, James R. Rae of Winchester and the late Stephen W. Rae. She was the grandmother of Kayla Grant and is further survived by many nieces and nephews, great-nieces and nephews.

Relatives and friends are kindly invited to gather at Costello Funeral Home, 177 Washington St., Winchester on Wednesday, September 16, 2026 @ 10:30AM followed by a Funeral Mass in St. Mary’s Church, 155 Washington St., Winchester, at September 16, at 12 noon. Burial will follow in Wildwood Cemetery, Winchester.