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Silva began construction at an early age, helping his father and brothers build a fallout shelter under their 1787 Colonial family house in Lexington, Massachusetts. Silva Brothers' Construction  built the first set for The Victory Garden and later were noticed by the producer of This Old House, Russell Morash, while they were working on a home. Morash invited them to become the permanent contractors for the show in 1988.
Silva also contributes to This Old House Magazine and other publications from This Old House ventures.
He has been married to his wife, Susan Silva, for over 30 years. They have two children.
The partners of Silva Brothers Construction are Tom, his brother Richard, and his nephew, Charles. Their work has been featured on numerous This Old House projects.