Richard Allan Carroll of Ocean Pines, Maryland, passed away peacefully surrounded by his children on February 23, 2026. He leaves behind a legacy defined by hard work, honesty, and a deep love for his family.

Richard was born in Milwaukee, Wisconsin, on September 21, 1950. During his childhood his family moved several times before settling in Maryland. He spent early years in Albany, New York and Salisbury, Maryland before the family eventually settled in Bladensburg in Prince George’s County. Richard attended St. Ambrose Catholic School in Cheverly from fifth through eighth grade and later graduated from Archbishop Carroll High School in Washington, DC in 1968, where he participated in football and wrestling.

He went on to study zoology at the University of Maryland. During and after his college years, Richard worked as a roofing contractor before beginning a long career as a mail carrier in Montgomery County, Maryland.

Richard eventually settled in Poolesville, Maryland, where he spent more than 25 years and raised three children with his former spouse, Robin Winstead. Though they later divorced, they maintained a caring and respectful relationship throughout their lives.

Richard was blue-collar to his core. For more than four decades he worked as a mail carrier, known for his reliability and dedication. He woke up around 5:30 every morning without an alarm clock and rarely missed a day of work. Even after long days delivering mail, he often continued roofing work on the side. Providing for his family was simply what he did.

He believed deeply in simple values: work hard, be honest, keep your word, and take care of your family.

Richard had a curious mind and loved learning about the world. He enjoyed reading, particularly history and factual books, and had a lifelong interest in nature and animal documentaries. He appreciated the simple pleasures in life — a good meal, time with family, a walk outside, and the ocean air along the Maryland coast.

Later in life, Richard retired to Ocean Pines, Maryland, where he enjoyed the quieter pace of coastal living and being closer to the water he loved.

Despite his tough exterior, Richard had a soft heart and often helped people who were struggling. His generosity and willingness to lend a hand were simply part of who he was.

Richard was preceded in death by his parents, Emily Carroll (2012) and Dennis Carroll (1993).

He is survived by his children, Michael Richard Carroll (41), Alicia Mavis Carroll (39), and Brandon Jonathan Carroll (37); his former spouse, Robin Winstead (72); and his siblings: Alice, Betty, Dennis Jr., John, Robert, Gregory, and Jeffrey.

He also leaves behind many beloved nieces and nephews, including Colin, Erin, Nathan, Heather, Leah, Brian, Kevin, Matthew, Liam, and Ryan, along with extended family members and friends who will miss him dearly.

A celebration of Richard’s life will be held on Saturday, April 25th from 4:00 PM to 7:00 PM at the Ocean Pines Yacht Club in Ocean Pines, Maryland.

In lieu of flowers, the family asks that donations be made in Richard’s honor to help fund a memorial bench overlooking the water in Ocean Pines — a place he loved dearly. 

In the end, a life is measured not by the things we accumulate, but by the example we set and the people whose lives were better because we were in them.

Richard lived a life grounded in honesty, hard work, and love for his family — values the Carroll family will carry forward for generations.

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