On the evening of Monday, November 29, 2021, Leroy John Shillingford transitioned peacefully at the Eliot Nursing Facility in Natick, MA.

Born on March 16, 1937 in Rosseau, Dominica, Leroy was spent the first 26 years of his life completing his formative education and achieving remarkable success as a sportsman. He represented his birth country, Dominica, and the Windward Islands for both cricket and football, serving as captain for both sports during his tenure.

Once he migrated to North America in 1963, he became focused on acquiring a college education in Montreal, Canada. Having established a life with a cherished circle of friends and finding his love, Shirley, he moved in 1969 to attend Northeastern University in Boston; many years after, he shared that ‘there was too much fun and many distractions among friends in Montreal to focus on his professional goals’. Having no financial means to pay for college, Leroy studied hard to earn the Martin Luther King scholarship to cover his tuition; he held many jobs to supplement his living expenses while becoming deeply entrenched in the Black Power Movement of the 1970’s. He always reminisced about those days of racial agitation to convey the importance of standing up for what is important and allowing nothing to stand in the way of accomplishing your goals. In the midst of his education, Shirley joined him in Boston and they had their first child together shortly before he graduated in 1973. He quickly enrolled at Suffolk University after earning his BA to pursue a masters degree while working for the City of Boston. Shifting to become an entrepreneur after completing graduate school and the birth of another daughter, he completed the Real Estate Institute of New England certification and opened Bowdoin Real Estate, where he found great success for more than 25 years. As one of 5 black real estate brokers in Boston during the 1980’s, he helped many people of color become homeowners while remaining committed to leadership roles for several organizations, including the Sisserou Club representing the interests of Dominicans in North America and on the island.

Survived by his wife (Shirley) and their daughters, Ventrice (husband, Wade Cole) and Dacia (Widow of Jay Compas and daughter, Neajah) together with his other children (Shyann, MacDonald, Alethea, Merna and Deborah), sisters (Sonia Burman, Claudia Joseph, Alex Hood, Patricia Robertson, Barbara-Ann Shillingford, Genny Walter, Imie James and Hazel Ann Sulaimon), brothers (Dr. Clayton Shillingford, Albert Shillingford, Ian Shillingford, Alister Shillingford, Dense Shillingford, Wilfred James, Cyril Phillip, Tyrone Shillingford-Lewis) and a host of grandchildren, nieces, nephews, cousins and dear friends. He is predeceased by his parents, sisters (Hilma, Gerald, Claudia and Anthea) and granddaughter, Natasha.

Visitation will be held at the Dolan Funeral Home, 1140 Washington Street, DORCHESTER LOWER MILLS on Saturday December 11th from 10-11AM. Funeral Service to begin at 11AM. Zoom link below.

Topic: Funeral Service for Leroy Shillingford Time: Dec 11, 2021 11:00 AM Eastern Time (US and Canada)

Join Zoom Meeting https://us02web.zoom.us/j/87012952954?pwd=K3hHZ1h2WXBMNm0zVDViUU5vZHd1dz09

Meeting ID: 870 1295 2954 Passcode: 023326