Penelope D. “Penny” Winters, longtime Southold resident, passed away on Sunday, July 5, 2026. She was 81 years old.

Penny was born on June 30, 1945 at Flower Fifth Avenue Hospital in Manhattan to Helen (née Davis) and Reginald B. Hudson. She was one of three children. She graduated Greenport High School with the Class of 1963.

On July 8, 1973 she married the love of her life, the late Richard A. Winters, and together they made their home in Southold. In her professional career she was a secretary for her father’s real estate business, R.B. Hudson Real Estate. She also worked at Southold Savings Bank and as a bus driver for Sunrise Bus Company.

She volunteered for Save the Bays, and was the Newsday Volunteer of the Year for Save the Bays in 2000. Majority of the time, and most importantly, she was a stay-at-home mom and loved her family dearly. She was a member of the Greenport United Methodist Church, and then the First Presbyterian Church of Southold. She was also a member of the Seagyan Club in Peconic. She loved being involved making food for various functions, and she made dinners for the elderly that were homebound.

Predeceased by her husband Richard; and brother Timothy Hudson; Penny is survived by her daughters Amy H. Bail (Samuel Jr.) of Laurel and Susan Winters of Southold; step-daughters Elizabeth Winters of Mattituck and Virginia Staron of Waynesboro, VA; grandchildren Hudson Bohn, Ryan Lademann and Tyler Lademann; great-grandchildren Kiernan Lademann, Prentice Lademann, Finnian Lademann, Enid Lademann and Una Lademann; sister Susan Hudson Roache of Palm Coast, Fla.; and niece Marie Roache of Flagler Beach, Fla.

The family received friends on Sunday July 12 at the DeFriest-Grattan Funeral Home in Southold. Funeral services were held on Monday, July 13 at the First Presbyterian Church of Southold, officiated by Pastor Garrett Johnson.

In lieu of flowers, donations to the Southold Fire Department Rescue Squad or Mather Hospital (Attn: Infusion Center) would be appreciated.

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