The house has always been more than a closed and functional structure; it is the most fundamental setting of human life—a space that is not merely limited to the function of shelter, but also a bearer of identity, memory, comfort, and social bonds. Among these, the landscape—including open and semi-open spaces as well as natural or artificial views—plays a decisive role in shaping the lived experience of the house. However, contemporary architectural trends have led to a rupture between the house and the landscape, resulting in diminished attachment, weakened social interactions, and reduced livability in residential spaces. Thus, the necessity of this research lies in exploring the relationship between house and landscape and clarifying the mechanisms of their integration in contemporary villa typologies, since rethinking this bond can provide a pathway to enhancing quality of life in today’s contexts. This article, by prioritizing the role of landscape in improving residential livability, analyzes the attributes of a livable house from a landscape-oriented perspective and comparatively evaluates the methods of integrating housing and landscape in contemporary villas. The research method is logical and deductive reasoning, using simulations of selected contemporary villas in Depthmap and Agraph software to examine how different mass/void compositions influence livability components. The comparative study covers six distinct spatial organization types of mass/void combinations. The findings indicate that among the examined indicators, accessibility and visibility play the most significant role in enhancing housing livability. Direct and orderly pathways increase presence and spatial dynamism, while open and fluid layouts of landscape-related areas provide the greatest degree of visual openness. Conversely, the indicators of depth and enclosure mainly contribute to preserving territories and private domains. Therefore, housing livability is achieved when these indicators are combined in a balanced manner—simultaneously enabling spatial interaction and the experience of natural views alongside the preservation of spatial privacy.