An early 19th century cottage in Willoughby’s heritage conservation area transforms through thoughtful extension, where a diagonal ridge beam rises northward, creating a kite-like roof that baths the interiors with natural light and frames views of nearby eucalypts. An inner courtyard bridges old and new while illuminating a basement level—home to a gym, playroom, and laundry—that serves as a tranquil retreat surrounded by greenery. The roof’s southern descent shelters an outdoor dining area, minimises garden shadow, and works with the land’s natural slope. Hardwood sliding doors and a matching staircase forge a strong connection between home and landscape despite level differences, while the elevated living space appears to float above the recessed basement, reducing visual bulk and creating a flexible secondary living space that parents and children equally enjoy.