During the opening phase of the Irish civil war, Dublin’s O’Connell Street was subjected to large-scale destruction of properties and businesses for the second time since the 1916 Rising. Utilizing newly available compensation claims as well as state and local government records, this research article examines four aspects of the post-civil war restoration of O’Connell Street for the first time: the scale of the destruction; the compensation scheme devised by the Irish government which accorded O’Connell Street a unique status in the Damage to Property Compensation Act of 1923; the context of the town planning regulations introduced, as well as the concerns of property owners, the local authority and central government; the process of reconstruction – how compensation was paid, what properties were rebuilt, in what manner and when.