Leonard Arthur D'Agostino

Leonard Arthur D'Agostino, a man of faith, passed away in his home on 1/20/26, surrounded by family, at the young age of 83. A public service/Celebration of Life, will be held at Beachside Baptist Church New Smyrna Beach on 3/20/26 at 6:30 pm

Lenny had a proud history, both personally and professionally. Before retirement, Lenny spent many years as President of the Greater New Haven Real Estate Board and as a Director of the State of Connecticut Real Estate Board, all while running his company, Arrow Real Estate. He later became an owner-operator of his own appraisal firm, still in existence today, ABC Appraisals, while also earning numerous professional designations.

Lenny is survived by his wife, Caroline Elizabeth, who worked alongside him in their real estate ventures. Together, they enjoyed a lifetime of loving partnership while raising their five children: Kathie (Neal), Robert, Kenny (Delia) Devra (Andy), and Sandy/Curly Top (Mike). He is also survived by his sister, Lynda and his brother-in-law Danny Greenlaw.

Lenny's passion for yachting became a beloved hobby that brought joy to the entire family. He kept his powerboat along the shoreline of Connecticut, living his days with marina friends and family and navigating each year to his favorite winter marinas in the Jupiter, Florida area. His family has countless memories of fishing from his docks, water skiing, and tubing down the Intracoastal—all with Papa at the helm.

Lenny's strength was extraordinary. Despite enduring medical challenges throughout his life, he remained physically and mentally resilient. He was unwavering in his commitment to staying strong, never missing his three-times-a-week gym workouts. His discipline and perseverance inspired those around him and spoke volumes about his character.

Lenny and Carol found their mainland paradise along the Intracoastal Waterway of Juno Beach, where Lenny proudly served as President of the Oak Harbour Condominiums. He passionately helped his neighbors maintain their beautiful homes, always taking pride as boats sat peacefully or passed by, and he hosted years of memorable Jupiter boat parade parties.

But Lenny was not only known as "Captain, My Captain"—he was loved simply as Papa. A grandfather to 14 and great-grandfather to 11, he smiled with tremendous gratitude, often sharing how thankful and blessed he felt to have the honor of living a life that positively impacted all of us. He took time to build a strong relationship with each of his grandchildren and great-grandchildren. He loved sharing their latest updates, talking about football with his grandson, showing up at kids' sporting events, playing snowball, and years of unforgettable Lake Winnipesaukee memories! The family and his friends will remember him for his humor, strength, amazing cooking, constant smile and love he had especially for his dear grandchildren.

He also felt great pride in having raised his grandson Glenn alongside his wife Caroline, through difficult times, never giving up on him and always believing in their young man to the very end; proving them so right.

A sincere thank you to his granddaughter Kaitlyn for her immediate response in helping the family when he was sent home with sporadic hospice support. Her tender care for all her family members will never be forgotten.

God bless our Papa. We love you always.