Henry Sylvestri
Plant a Tree
Plant a Tree


11:00 am
Friday, May 3, 2019
Blessed Sacrament Chapel
Route 9W
Fort Montgomery, New York, United States

Final Resting Place

Eagle Valley Cemetery
Route 9W
Town Of Highlands, New York, United States

Obituary of Henry Joseph Sylvestri



Henry Joseph Sylvestri

March 30, 1923 – April 23, 2019

Town of Cortlandt, NY


Henry J. Sylvestri was a wonderful gentleman that was loved, is missed, and will always be cherished.  Henry peacefully passed away on April 23, 2019.

Henry was born on March 30, 1923 to Donato and Jenny Fasciano Sylvestri in Ossining, NY.  He was the second of six children.

Henry volunteered in World War II, was selected for the United States Merchant Marine Academy at Kings Point, and graduated on November 23, 1945.  As a Cadet Midshipman he sailed six times across the Atlantic Ocean, bringing fuel to England for the D-Day Invasion and the Allies’ war effort. Henry was proud of his service to his country and his greatest reward was his participation on Hudson Valley Honor Flight Mission 22.

Following two more years at sea, Henry joined the Travelers Insurance Company as a safety engineer.  He worked in Detroit, Albany, and Newburgh.

On August 1, 1948, Henry married the love of his life, Mary Anne Fasana.  They met on a blind date, set up by their two sisters, Ellen Wright and Florence Perry, friends working together on jeeps at the Fisher Body plant. Henry later returned the favor introducing both Ellen and Florence to men they would marry. Henry and Mary were fortunate to have achieved sixty loving years of marriage at the time of her passing in 2008.

In 1961, Henry became an independent insurance agent and real estate broker as Henry J. Sylvestri Insurance and Real Estate in Fort Montgomery.  Henry helped several generations of New Yorkers with their real estate and insurance needs before retiring in 2003.

Henry was involved in his community.  Some of Henry’s volunteer and positions include: elected to the Schodack Central School Board, served on the Board of Directors of the Marine Midland Bank and Highland Falls Savings and Loan, the Lions club, Town of Colonie Senior Men's Golf League and participated as an active parishioner of Blessed Sacrament Chapel in Fort Montgomery.

Henry was an outdoor enthusiast, he had a deep appreciation for nature, and he enjoyed socializing and playing sports with family and friends.  Henry could be a fierce competitor and was well-known for sinking critical putts. He was still playing golf at 95.

In 2003, Henry moved with Mary to Latham, NY to be closer to two of their daughters. Henry happily returned to his home on the Hudson River in November 2018 and was welcomed back by many old friends.

Henry is survived by three daughters, Susan (Milton) Lawney of Colonie, NY; Jane S. Oswald of Latham and Fort Montgomery, NY, and Gloria Edelen of Monterey, CA.; one sister, Joan (Booth) Mattson of Saratoga, NY and grandchildren, Heather (Colin) Shafer; Matthew (Gina) Lawney; Elizabeth (Eric) Olsen; Victoria (Vijay) Culas; Alexandra (Jason) Chou; Rhett (Alicia) Edelen; Michael Edelen and great grandchildren, Lindsey & John Shafer; Samantha & Bella Lawney; Jay & Nick Olsen; Ozzie & Henry Culas; and Nate & Charlotte Chou.

Henry’s family would like to offer a special thank you to Dr. Shah Nawaz for his dedication to Henry, his guidance in palliative care, and his efforts to maintain the best quality of life for Henry these past six months.

A Funeral Mass will be held at 11:00 a.m. on Friday, May 3rd at the Blessed Sacrament Chapel in Fort Montgomery.  Interment will follow at Eagle Valley Cemetery in the Town of Highlands, NY.

Memorial contributions may be made to the Highland Falls Library Children’s Space, 298 Main Street, Highland Falls, NY 10928.

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