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The waterfront area itself is taking off with commercial and residential developments, and the adjacent South Boston section of the city is also booming with brand-new or converted loft/condo buildings. There are also some recent high-rises downtown and in Chinatown, but they tend to be "high end" in terms of cost. And that area is very much in transition - in other words, between the decline of Downtown Crossing and there being remnants of the former Combat Zone in Chinatown it's still pretty sketchy after dark.
Beacon Hill, Boston's counterpart to DC's Georgetown, is perenially popular with its brick row houses along tree-lined "gaslit" streets. It's said, and I can vouch from experience, that the stairways inside Beacon Hill buildings are the narrowest and steepest in town. So hire a crane if you're going to be bringing a piano or a big bed and/or couch, lol.
The North End started getting "discovered" about 25 years ago, but still clings to its Italian feel in spite of all the transplanted newcomers and the suburban migration of most of the original families. You still have umpteen choices of gelaterias and restaurants with menus from the old country. And the streets still come alive during the summer for the various saints' parades and festivals. The housing may not be much to look at from the outside - block after block of brick tenements over commercial establishments - but of course you can do whatever you want to a place inside. Lots of people have.
All of these neighborhoods are but three subway stops - at most - away from South Station, whence there's a glorified bus route called the Silver Line which serves the waterfront en route to the airport. On days with good weather you could easily walk all the way to and fro.
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