There are a couple of items to take into consideration.
First, the previous respondents are correct. You should check with the City, particularly Dept of Buildings for paving limitations. The city may have restrictions because of the increased storm water run off from the site once it's paved. They may require that you install a new storm sewer line to deal with the run off. In general, you may want to consider a permeable paver solution to allow storm water to be percolated into the ground. This may reduce or eliminate the need for a storm sewer which can be very costly.
Second, pay particular attention to what a paved area of the buildings and homes surrounding you. I am assuming that you will not own this home forever, and a front pad of that size in South Shore may be very unsightly, making your home less attractive to a future buyer.
I work with a lot of buyers and sellers in South Shore, and am fairly familiar with the property/lot types. If you have a lot with a curb cut and a side drive, with no alley access, consider pavining the side drive and a portion of the rear to accomodate your parking. This would have a positive impact on desirability for future resale.... more