Winter Hill
Winter Hill is one of the fastest gentrifying areas in all of Somerville, and I am a huge fan. It's roughly bound north of Medford Street, west of McGrath Highway, and east of Magoon Square.
Barack Obama lived in Winter Hill at 365 Broadway Avenue while he was attending Harvard Law. It also previously was the home base of Whitey Bulger and the Winter Hill Gang back many moons ago.
Before the Gilman Square Green Line came in a few years ago, this area attracted a lot of commuters who were commuting by bike and bus, and as a result, rents were relatively low. But now with the Green Line in place, we've seen significant growth both in property values as well as rental prices as young professionals commuting to downtown Boston have come to this area in droves in the last handful of years.
Winter Hill is also home to Sarma, arguably the number one restaurant in all of Somerville. It's an excellent place to go to if you can get a table or come right when it opens and grab a seat at the bar (pro move!).
Winter Hill also has Foss Park, directly on Broadway - it has a lot of amenities including a combo turf football/soccer field, two tennis courts, a baseball diamond/softball/little league field. There's also a separate playground there for older kids as well as toddlers, plus a public swimming pool in the warmer months.