Penelope D. “Penny” Winters of Southold died July 5, 2026. She was 81 years old.
Born June 30, 1945, at Flower Fifth Avenue Hospital in Manhattan, she was the daughter of Helen (Davis) and Reginald B. Hudson. She graduated from Greenport High School in 1963. On July 8, 1973, she married Richard A. Winters, and they made their home in Southold. She worked as a secretary for her father’s business, R.B. Hudson Real Estate, and also worked at Southold Savings Bank and as a bus driver for Sunrise Bus Company. She volunteered for Save the Bays and was named Newsday Volunteer of the Year for Save the Bays in 2000. She was a member of the Greenport United Methodist Church and later the First Presbyterian Church of Southold, and was also a member of the Seagyan Club in Peconic. She enjoyed preparing food for various functions and made dinners for homebound elderly residents.
She was predeceased by her husband, Richard, and her brother, Timothy Hudson. She is survived by her daughters, Amy H. Bail (Samuel Jr.) of Laurel and Susan Winters of Southold; her stepdaughters, Elizabeth Winters of Mattituck and Virginia Staron of Waynesboro, Virginia; her sister, Susan Hudson Roache of Palm Coast, Florida; her niece, Marie Roache of Flagler Beach, Florida; three grandchildren; and five great-grandchildren.
The family received friends July 12 from 3 to 7 p.m. at DeFriest-Grattan Funeral Home in Southold. Funeral services were held July 13 at 11 a.m. at the First Presbyterian Church of Southold, officiated by Pastor Garrett Johnson. Memorial donations may be made to the Southold Fire Department Rescue Squad or to Mather Hospital (attn: infusion center).
