This study explores the design characteristics of approach spaces in architect Yoshiji Takehara’s independent residential works, focusing on their spatial arrangement, sinuosity, and experiential qualities. Through the analysis of Takehara’s projects and interviews with the architect, the research identifies key patterns in approach configurations, including entrance positioning, path complexity, and site-specific adaptations. The findings reveal that Takehara’s designs emphasize winding paths and deliberate spatial sequences, contrasting the simpler approaches of contemporaneous residential designs. The study categorizes approach configurations into distinct typologies, influenced by the site dimensions and entrance placement, and highlights a shift from physical obstructions to subtler, psychologically guided design elements over time. Takehara’s design method translates the concept of “Ma” from traditional tea gardens into the language of modern pathways, integrating traditional Japanese spatial ambiguity into contemporary residential design. This offers strategies to enhance spatial perception and experiential richness. Particularly in compact urban settings, the research provides valuable insights for contemporary residential design, emphasizing the importance of landscape-oriented approaches and spatial sequencing in creating meaningful entry experiences.