During its first year the Society established a Building Fund. As the fund grew, the officers looked for an appropriate property for their headquarters. In 1925 the house then known as the 1640 Lt. Walter Fyler House, thought to be one of the oldest wood-frame houses in the state, came on the market. To the horror of Society members, one prospective buyer wanted to use the site for a gasoline station. The Society signed an option, solicited donations, received them enthusiastically from all over the United States, and purchased the house.
Donations began to pour in: books, artifacts, documents, maps, and photographs. In its early years, the Fyler house operated as a historic house museum, archives, tea room, and hostel. Visitors from afar with Windsor roots could even stay overnight in one of the historically furnished rooms.