Anthony Sillo, a seventy-year resident of New Canaan, Connecticut passed away at home after a long, wonderful, full life on November 13, 2025 at the age of 87.
Anthony Sillo
Anthony was born in the province of Frosinone, Italy in the town of Settefrati, just 20 miles north of Montecassino, on January 8, 1938 to Michele Sillo, a stone mason and Maria Donata Sillo (nee Volante). At the age of 17, he accompanied his father to New Canaan, Connecticut in 1955 and were joined by his mother and brothers a few years later. On April 4, 1959, Anthony married his childhood sweetheart, Alessandra (Sandy) Massarella. Anthony continued to work alongside his father, and then as a landscaper, fine-tuning his knowledge of sitework and building. In the 1960s, Anthony attended night school in New Canaan to study English and obtain a better understanding of American society and culture.
Anthony and Sandy went on to raise their family of four children in New Canaan while building their business. In 1972, he formed a residential home building company, Anthony Sillo Incorporated, which was well known for old world craftsmanship and consistently demonstrated a strong dedication to hard work and quality construction. Over many years his three sons worked for him and learned the business and gained valuable experience. They all subsequently went on to form their own building businesses carrying on the important values, traditions and ideals. Anthony Sillo built over 80 homes for New Canaan families during his career. He showed tremendous pride in “his houses” and remained great friends with his customers for years to come.
Anthony and Sandy were truly committed to their family and extended families. They worked together to enjoy and perfect several interests and skills which they learned as young people in Italy. “Tony’s wine” and winemaking was a source of great pride and ultimately, inspiration for his sons and grandsons who carry on the tradition. Anthony and Sandy also made homemade prosciutto, sausages, “jarred tomatoes”, and other Italian delicacies which were, and are, integral to their upbringing and culture. They were avid and prolific gardeners whose fig trees, vegetable plants, flowers and beautiful landscaped yard provided a wonderland for their eleven grandchildren to enjoy over the years.
In addition to his commitment to his family and to the New Canaan community, Anthony maintained a close connection with his hometown and his heritage over the years by visiting Italy several times and participating in the 700 year old historical religious festival (Festival in honor of Madonna di Canneto) which reveres the Assumption of Mary each year in August. He also contributed to the local Italian American community by serving as President of the Columbus Center of New Canaan. Anthony was very interested in politics, and followed world economies, current events and business as evidenced by his interest in news casts and nightly news shows.
Anthony and Sandy were very proud to have become citizens of the United States of America.
Anthony is survived by his wife of 66 years Alessandra Sillo of New Canaan, son Michael Sillo of New Canaan, son Rocco Sillo (Johanna) of New Canaan, daughter Donna Socci (Joseph) of New Canaan, son Anthony Sillo Jr (Rachele) of New Canaan, brother Dominick Sillo (Leslie) of New Canaan, brother Joseph Sillo (Marnie) of New Hampshire, sister in law Marie Massarella of New Canaan, grandchildren: Anthony M. Sillo (Alexandria), Katheryn Vittoria (Joseph), Robert Sillo, Philip Socci (Taylor), Alessandra Socci, Alexander Sillo, Emma Sillo, Sandy Sillo, Ricky Sillo, Christie Sillo and Kimberly Sillo; as well as eight great-grandchildren; several nieces, nephews, grandnieces and grandnephews; and other beloved extended family . Anthony was predeceased by his parents, a brother Joseph Sillo in Italy, his mother in law and father in law Loreto and Donata Massarella, and his brother in law and best man Anthony Massarella.
A Mass of Christian Burial will be celebrated on Wednesday, November 19, 2025 at 10 am at St Aloysius Roman Catholic Church, 21 Cherry Street, New Canaan Connecticut 06840 followed by internment at St. John Cemetery Norwalk, 223 Richard’s Avenue, Norwalk, Connecticut 06850. The family will greet visitors beginning 9 am at the church that morning.
The family is being compassionately cared for by the staff at Hoyt Funeral Home, 199 Main Street, New Canaan CT 06840. For online condolences please visit www.hoytfuneralhome.com
