William Daniel Dobrowolski

William D. Dobrowolski, Sr. of Portland passed away peacefully in the evening of September 11th at Bay Square, Yarmouth. Bill was a loving husband, father, grandfather, great grandfather, and a well-respected member of his community. Bill was born on May 25, 1935 in Paterson, NJ the son of Joseph and Stefanja Dobrowolski. Bill grew up in Ridgewood, NJ where he graduated from Ridgewood High School in 1953. After High School, Bill attended Columbia University on a NROTC scholarship, graduating in 1957 with a BA in Liberal Arts with a concentration in Economics and Philosophy. While at Columbia University, he met his wife Sheila who was attending St. Luke’s School of Nursing in New York City. They wed in 1957 and were happily married for 58 years until her passing in 2015. After serving as a U.S. Marine Corps Infantry Officer from 1957 to 1960, Bill and his wife Sheila moved to Maine and made Portland their home to raise their four children.

Bill started his dynamic executive career with Union Mutual (now Unum) from 1960 - 1969 becoming Vice President responsible for Mortgage, Real Estate, and Bond Portfolios. Bill continued his career in New York City from 1969 - 1982 in Commercial Mortgage and Realty Investment commuting home to Portland every weekend. In 1982, Bill advanced his career in Dallas with Sunbelt Savings as Executive Vice President and President of Service Corp continuing his commute home to Portland every weekend until 1985. Bill then became Principal of Real Estate Holding Companies in CA working primarily from the office of his home in Portland.

Bill was a quiet man of strength and character and civic responsibility was of great importance to him. He was a man who generously gave his leadership, hard work, civic mindedness, and spirit to his community. During various years of retirement, Bill was on the Board of Real Estate Appraisers and a qualified expert witness for the State of Maine, a Board Director of Portland’s Chapter of Habitat for Humanity, a Member of Portland’s Housing Comprehensive Plan Committee, and a Stroudwater Village trustee from 1994 until 2012. Bill also donated his time to the Bruce Roberts Toy Fund wrapping presents for children for a few Christmas seasons. Bill was a gracious man who never forgot his humble beginnings. In ending a conversation whether in person or on the phone, he would always ask if you needed anything or if there was anything he could do for you. Bill was loved and adored by his family and friends and he will be greatly missed.

Bill was predeceased by his wife Sheila Jones Dobrowolski; parents, Joseph and Stefanja Dobrowolski; a sister, Olga Baron; two brothers, Walter Dobrowolski and George Dobrowolski; and a nephew, Walter Dobrowolski, Jr.

He is survived by three daughters, Kathryn J. Dobrowolski (Andre) of Yarmouth, Sheila Gayle Dobrowolski of Portland, and Kristen Dobrowolski Walker of Portland; a son, William Daniel Dobrowolski, Jr. of Florida; five grandchildren, Devin Dobrowolski (Rachael) of Southwest Harbor, Dakotah Walker (Rachel) of Boise, Idaho, Dylan Waterhouse of Saco, William Waterhouse of Milo, and Diana Dobrowolski of Portland; three great grandchildren, Lucy Walker, Cillian Dobrowolski, and Harrison Walker; two nieces, Debra Kadar of Bear, Delaware and Linda Taylor of Huntsville, Alabama.

Family and friends are invited to attend a time of visitation on Sunday, September 28, 2025 from 2:00pm to 4:00pm at Jones, Rich and Barnes Funeral Home, 199 Woodford Street, Portland . A Celebration of Life will be held at DiMillo’s restaurant on Saturday, June 20, 2026 from 1:00pm to 4:00pm so distant family members may attend. Internment will be private.