Penelope was the first President of the Co-operative Housing Federation of Toronto (CHFT) at its incorporation 50 years ago. 1974 was a busy year for her as she was also a founding member of Dufferin Grove Housing Co-op along with fellow CHFT honoree, Jon Harstone, her husband at the time.
Three years later, she became the first co-op co-ordinator in Toronto when she was hired by Alexander Park Co-op. She moved into housing development work in 1982, joining Chris Smith and Associates, a co-op resource group where she developed several projects including Niagara Neighbourhood Housing Co-operative. During the 1980s, Penelope did a turn as a board member of Co-operative Housing Federation of Canada.
Winter joined the CHFT staff in 1991 as a Member Services Consultant and in 1993 she was hired by CHF Canada to provide services in French and English to co-ops across Canada.
In 2007, she became the Director of Operations at the newly formed Agency for Co-operative Housing where she worked until 2012. She returned to co-op management forming her own property management firm in Ottawa and retired from that work in 2018. Penelope is delighted that two of her four children and her grandchildren live in co-ops in Toronto and Ottawa. CHFT is proud its long connection to Penelope Winter and made her a lifetime board member in 2001.