Functions and meanings of the homes are being expanded due to the global pandemic situation. And various design elements and methods in order to enhance mind & physical comfort are becoming more important than ever. Among them, windows are emphasized as a central element. Steven Holl is a representative architect who has continued experimenting and realizing architectural spaces with windows as medium. Therefore this paper discusses values and methodological characteristics of windows in Steven Holl's residential projects. Among the 23 residential projects that have been carried out since the 1970s, seven cases were carefully selected, those which best represent the architect’s architectural message based on three major periods of his works. The results are as follows. Steven Holl’s windows in residential designs can be classified into four types: medium as to overcoming nature, medium for controlling continuity, energy circulation ring between internal and external system, and primitive sensitivity recovery. In conclusion, Steven Holl's windows expanded their roles and practical values in a form that focuses on the internal characteristics of space through continuous experiments and practice. Therefore, these results may contribute in developing practical solutions in designing diversified residential spaces especially in and after this pandemic period.