Randal Simon

KENNEBUNKPORT – Randal Simon departed our community on the morning of July 6, 2025, at the Maine Medical Center with his beloved wife and daughter by his side. He started life on March 3, 1948, first on Long Island and then in New York City, N.Y.

Randal’s inherently pioneering spirit, in combination with his drive to improve the world around him, was evident from an early age, whether it was going door-to-door selling All About Books as an 11-year-old or, while attending McBurney School for Boys and somehow convincing the administration—ever the salesman—and to the envy of every classmate, that he be allowed to leave school every day at noon so that he could go to work, “to support his divorced mother.” His mother was totally unaware of this until just before graduation. (Ah, how administration and parental vigilance have changed!)

His work evolved after graduating from Nasson College when Randal and two other educators started a small, one-room schoolhouse for grades K-8, aptly named Community of Children. This concept was virtually unheard of in the early 1970s, but the educational legacy lives on within the lives of the students to this day.

He and Deborah were married in a private, civic ceremony in 1973, attended only by their big, beautiful Newfoundland “Happy”…enough said. They have celebrated a deep and generous love and friendship for 52 years…and will continue to do so.

Reluctantly, they left Maine and relocated to Stonington, Conn., where Randal became a faculty member at Pine Point School and, subsequently, Assistant Headmaster at Hamden Hall Country Day School (K-12) in Hamden, Conn.

He returned to Maine when a friend offered him a position in her newly created real estate company (Aiello & Co). Ever-on-the-move, he then established Prudential Prime Properties (later Berkshire Hathaway) with two other partners. After a number of years, he went on to Sotheby’s International Realty and, only recently, joined his long-time teammate at Kennebunk Beach Realty.

In keeping with his mantra of, “Doing well by doing good,” he created a long-running real estate question and answer column, appropriately entitled ‘Simon Says’. It appeared for many years in the York County Coast Star and Tourist & Town magazine. All the while serving on a variety of boards and committees.

Randal, was at once a very public figure, quick with his signature humor and fun (“phone call…your pizza is ready!”), both in his professional and personal life. But, at heart, he remained a very private human being, unabashed in his love and devotion to Deborah, which only expanded in his love for his daughter.

In keeping with his wish for privacy, there will be no formal service.

Friends, neighbors and community are gathering separately to recount his many “Randal-isms.” He is remembered for his humor, his good-natured but often irreverent one-liners (you may know “the one”), but also for his passion for life and desire to contribute. Let those continue to be embraced and celebrated.

He leaves his broken-hearted, but ever-grateful, wife Deborah Langshaw; daughter, Rebecca Langshaw-Simon, son-in-law, Seth “Thomas” Fenn, young granddaughter, Charlotte of Kennebunkport; and niece, Melissa Wood and her husband Tom Miller of Arlington, Mass.

To share a memory or leave a message of condolence, please visit Randal’s Book of Memories Page at http://www.bibberfuneral.com.

Arrangements are in the care of Bibber Memorial Chapel, 67 Summer St., Kennebunk, ME 04043.

Donations in Randal’s name may be directed to St. Jude’s Children’s Hospital or any endeavor devoted to the betterment of the community in the state of Maine.