Ring-strain-enabled transformations have made significant progress, pushed the boundaries of unexplored chemical space, and emerged as a powerful tool for constructing complex molecules selectively and efficiently. Among the strained ring systems, [1.1.1]propellane, bicyclobutane (BCB), and azabicyclobutane (ABB) have garnered substantial attention and found numerous synthetic applications. In contrast, the chemistry of bicyclo[2.1.0]pentane, commonly known as housane, is scantly explored due to the lack of modular synthetic approaches. Herein, we describe a highly stereoselective, catalytic strategy for synthesizing polysubstituted housanes with up to three contiguous all-carbon-quaternary centers. The reaction is very efficient, works under mild conditions, requires visible light and organic dye as a photocatalyst, and exhibits a broad substrate scope. Furthermore, we have also developed a highly diastereoselective Paterno-Buchi reaction for synthesizing spiro-oxa-housanes, which are novel molecular entities in the literature. The post-synthetic diversification of the products via a strain-release driven diastereospecific 1,2-ester migration that allows the rapid synthesis of functionalized bicyclic imides further highlighted the synthetic utility of the current protocol. Combined experimental studies and computational investigations revealed the origin of the reactivity and stereoselectivity.