The History of Winning Homes

Winning House buildings in 1941. Lester Fuller Smith collection photograph of various buildings of William H. Winning. Photo Courtesy of Winchester Archival File.

After the passing of William Henry Winning on October 25, 1898, John W. Johnson of Woburn, Daniel W. Pratt of Winchester, and Howard M. Munroe of Lexington set out as the named trustees for carrying out Mr. Winning’s requests to turn his home place of one hundred and forty acres to be used and appropriated as an establishment and maintenance of a home for orphans and other destitute children.

The trustees of Winning’s estate in Woburn, Lexington, and Winchester renovated the house to accommodate 20 children at a time for a two week stay, in addition to the temporary care of an additional 160 children in order for them to escape the congestion of the local area. In 1901, the Winning Home Corporation was created, and the property was purchased for $1 from the trustees.

The Winning Property offers both children and adults alike a place to enjoy summer camp, horseback riding, picnics, and overall enjoyment to this day.

Throughout the years, the property has continuously expanded the facilities and services that are offered to children and their families. Volunteers, groups, and organizations from the local area have come together to help with this expansion, including clearing trees and earth to make additional room for roads and swimming pools, constructed new kitchens and the cabinets that are in them, building merry go rounds, and creating petting zoos.

Recently, the Board that manages Winning’s legacy and the Winning Property, also known as the Winning Farm or the Winning Farm for Children, made the determined the best way to protect the property and it’s financial stability of the Winning Home Corporation as well as continue to help local children was through selling the land assets of the Winning Home. The outcome of the sale was cash assets for long-term investment, which preserves around 50 acres of land as permanent open space.

Since the conversion from landowner to charitable trust, the Winning Home has remained true to the intent of William Henry Winning, providing services and supporting children who are economically, socially, physically, emotionally, or mentally handicapped or disadvantaged and their families. The Winning Home has also made grants over $5 million to local charitable organizations.