Whether you are rightsizing from Wellesley or coming from Chicago, these are words of wisdom coming from having lived here all my life.
The City of Boston has 23 “sanctioned” neighborhoods and often, within these, you’ll find smaller communities. These enclaves define areas such as Kenmore Square, Cleveland Circle, the Charlestown Navy Yard, Ashmont, Bay Village, Fort Point, to name only a few.
Wherever you’re moving from, the location you choose is critical to your happiness and as evidenced above, since each neighborhood is distinct, you not only have to decide on old vs. new, a tower or small building, proximity to transportation, greenery, groceries, shopping, and amenities, but the exact community that meets your physical and psychological needs.
Though they are all separate communities, parts of Cambridge, Somerville and Brookline are in fact more densely developed and closer to downtown than outlying Boston neighborhoods. While Brookline separated from Boston in 1705, it’s almost surrounded by the city. As a result, you may accidentally stumble into its Victorian mansion- and brownstone-lined streets without ever realizing you’ve crossed any borders.
Secondly, in my experience, one clearly doesn’t need a car in Boston. Given that your chosen neighborhood will likely come complete with bus routes, bike lanes, and maybe even a subway stop, Boston is one of the nation’s most walkable city.
Whichever your vicinity, I have one promise. You will never be bored. See Boston Properties