James Robert (Bob) Houskeeper, 91, died peacefully on August 16, 2021, at his home in Hudson, Florida, after a long illness.
He was born July 27, 1930, in Montclair, New Jersey, the son of the late Peter and Margot (Young) Houskeeper. His family moved to Peekskill, New York, where he attended grade school and high school before attending Columbia University in New York City on an ROTC Scholarship. He was one of the Naval Reserve midshipmen from the university to cruise to Europe for summer training on Task Force 61.
In the early 1950s, Bob served in the U.S. Navy in the Seabees branch, officially known as the United States Naval Construction Battalions. He was stationed in Subic Bay in the Philippines during the Korean War, and felt tremendous pride having served on the Battleship Missouri.
Bob married Elizabeth Keon in 1954 and they raised seven children in Putnam Valley, New York, and Manchester, Vermont. They divorced in 1983.
Early in his career, Bob ran a tree service business and later operated Houskeeper’s Sawmill in Putnam Valley until the late 1960s. He also started his own professional building business and constructed a variety of contemporary homes on Sunrise Drive.
Passionate about his community and never one to sit on the sidelines, Bob threw his hat into the local political ring, serving as Putnam Valley Town Councilman from 1964 to 1973, and Putnam Valley Town Supervisor from 1974 to 1979. One of the highlights of his political career was meeting and having his photograph taken with Governor Ronald Reagan at a political event in White Plains, New York, in 1978. Bob proudly displayed that photo of him and Reagan for the rest of his life.
In his free time, Bob enjoyed boating and fishing on the Hudson River and Long Island Sound. He began visiting Vermont with his family in the early 1970s, skiing on weekends at Bromley and Stratton, and going deer hunting with friends. In 1976, Bob purchased a home, which he named Tanner Brook Farm, in Manchester, Vermont. He moved to Manchester with his family full-time in 1979 and resided there until the early 1980s.
He married Dolores Guadagnino in 1983. They lived in Mahopac, New York, and retired to Hudson, Florida, where they have spent the past 20 years. Together, Bob and Dolores enjoyed boating, visiting family, taking walks with their dogs, and socializing with friends. During Bob’s retirement, he was passionate about national politics, planting and tending to tropical trees and flowers in his yard, and being president of the Ronald Reagan Republican Club of Heritage Pines. He followed the stock market closely and worked in his final years as a timber broker.
Bob will be remembered for his larger-than-life personality and the stories he shared from his youth and his time in smalltown politics. He also loved talking on the phone with his children, sending political and patriotic emails, and spending time with Dolores, as well as with family, friends, and his dogs, Rylee and the late Char-lee.
Survivors include his wife, Dolores Houskeeper of Hudson, Florida; his children and their spouses: Jeanne Chisamore of Manchester, Vermont; Bernadette Dooney of Hopewell Junction, New York; Peter Houskeeper and fiancé Claudia Mitchell of LaGrange, New York; Robert Houskeeper and Jamie Henson of Encinitas, California; Matthew Houskeeper of Manchester, Vermont; Margaret Houskeeper Ohrn and John Ohrn of Newburyport, Massachusetts; Erica Houskeeper and David Barron of Burlington, Vermont; and his grandchildren Margo, Eric, Henry, Sam, Sophie, Ryan, Jack, Kristy, Kelsey, and Phoebe. Bob is also survived by his sister, Virginia Wilkins of Bridgewood, Tennessee; his step-children, Lisa and Robert Guadagnino; and his first wife, Elizabeth O’Leary of Manchester, Vermont.
The family would like to thank Bob’s caregivers from Chapters Health Hospice Care. Bob’s family is also enormously grateful to his doctor, Dr. M. Joud of Brooksville, Florida, and his oncologist, Dr. Ayman Barakat of Spring Hill, Florida.
Visiting hours will be September 25, 2021 from 2 p.m. to 6 p.m. at Heritage Funeral Home, 35 Morrissey Drive, Putnam Valley, New York. Flowers, cards, and/or memorial contributions to the Arbor Day Foundation are all welcome.