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There’s a very important resource on the Office of Planning – Historic Preservation Page that is a pamphlet that deals with additions, basements, and other alteration to building in historic places. This can vary considerably from case to case, from house to house, and on the “historic value” of a certain property or city block. I think that you should seek the advise of a professional who can help you navigate the different requierements for historic preservation and zoning -they also have a say in this. Ultimately, your house should be structurally sound to be able to perforate an entrance in the existing structure or should be made structurally sound, all while complying with all historic preservation requirements.
This is a link to the Design Guidelines about basement entrances and areaways:
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