Several examples survive from the 1880's to the late 1960's for Ontario communities. Every property is owned by someone or something. Ownership is tracked and managed by a flurry of legal documents. County and City Courts, City Archives and registry offices hold such records. Such requests usually involve a small fee for service.
Surveys are also available at the registry office.
Related to the above are personal and family papers - usually found in the local archives or museum. Tragically however, many families never think the 'paper trail' they generate over the years has historical value. It is very common for old letters, scrapbooks and photo albums to be tossed into the garbage or sold to a flea market dealer - especially after the last surviving relatives die. Most archives and some libraries hold photographic collections. Photographs are probably the best tool for identifying lost features on a house or building.