Property sale transaction is part of human activities that occurs on daily basis in urban areas across the globe. Sale and purchase of landed property synchronise, involve many stakeholders and activate great deal of movement and consultation in both formal and informal markets that still subsists in many countries, during period of tranquility and free movement to conduct business as usual. However, during pandemic period, and for instance, pandemic period of covid-19, there was lockdown of the national and global economies in 2020 and human movement was severely restricted, thus pronounced digitalization of doing business. This paper, using secondary data, presents an overview of procedures of land sale transaction and means of conducting them before, during and post covid-19 pandemic period with a view to enhancing smartness of estate surveyors or land agents and giving maximum satisfaction to real estate buyers at all times. The paper also expounds benefits and risks of and barriers to use of appropriate applications and software and future trends in land transaction procedure in Ibadan, Nigeria. Structured questionnaire was used to generate data from 20 firms of estate surveyors and valuers and 14 ministries and agencies on digitalization of property sale transaction operation. Frequency and percentage were used to conduct data analysis which showed that 100% of the respondents were fully aware of digitalization and its risk and had superficially gone digital in their operations but government organizations in charge of land administration and management were yet to digitalize their systems.