What is it like to live in Winter Hill?

Location, Location, Location Somerville
Shops line Broadway. Keith Bedford/Globe Staff

Erika Tarlin moved to Winter Hill in 1995 in part because her former neighborhood, Porter Square, had grown too expensive. She quickly found, however, that she liked more about her new Somerville neighborhood than the price.

The densely settled area was packed with lovely compact gardens and neighbors who had been there for years and knew all the stories on every corner. Two decades later, Tarlin still lives in Winter Hill.

Today, the librarian is seeing Winter Hill endure some of the same price dynamics that other nearby neighborhoods have faced. Property values are increasing as the area anticipates the Green Line extension, and some owners are looking to extract more in rent.

This is giving longtime property holders a financial boost and helping many spruce up, but it also means people are getting squeezed out as the historically affordable neighborhood becomes less so.

“If you had three kids, how could you rent an apartment?’’ Tarlin asked. “If you’re not working anymore and living on whatever you’re living on, how do you afford an apartment?’’

Tarlin hopes, however, that the increasing interest in Winter Hill will help spur a revival along Broadway, which provides few dining and entertainment options as it runs through the neighborhood.

There have been positive signs, she said, like the opening of Winter Hill Brewery, which joins the neighborhood mainstay Winter Hill Bakery as a draw on the main drag. But the community, framed by Medford and Pearl streets, McGrath Highway, Magoun Square, and Interstate 93, is waiting for other things to materialize. It still lacks a supermarket in the neighborhood center; a Star Market there closed years ago.

Tarlin and others are hoping that an ongoing city effort to come up with a long-term plan for Winter Hill will help the neighborhood hold on to a history that goes much deeper than the notorious gang that made it famous.

“It’s nice to see there are a core of people who are determined to want to stay, and to do that, the place has to be put together properly,’’ Tarlin said.


The building on Broadway where former president Barack Obama lived. —Keith Bedford/Globe Staff


The year that former president Barack Obama moved to Winter Hill. He lived in the building at 365 Broadway (above) while he was studying at Harvard Law School, and moved out in 1991. Most people called the future world leader Barry at that time. Obama reprised his role as a Winter Hill resident when he called into a radio show with then-Governor Deval Patrick in 2014, identifying himself as “Barack Obama, formerly of Somerville.’’

120 feet

Height of the slope that gives the neighborhood its name. Winter Hill played a crucial role in the Revolutionary War. Paul Revere traversed the area during his Midnight Ride, and Winter Hill — along with Prospect Hill — became a key stronghold in later fighting; it played an important role in the Americans’ successful retreat after the Battle of Bunker Hill.


The year St. Ann Parish was established in Winter Hill. It was founded in part to serve the burgeoning Irish population, and soon included the growing Italian community, too. St. Ann has evolved to meet the needs of other groups. It now offers services in Haitian Creole along with English.




Green Line extension

When the long-delayed project is complete, residents of Winter Hill will be able to walk more easily to an MBTA rapid-transit line that will carry them into Cambridge, Boston, Brookline, and Newton.


The neighborhood center

Though Broadway has functional offerings such as banks, pharmacies, and a post office, there are not many leisure activities in the center of Winter Hill. Some residents hope one upside of the gentrification will be an increase in entertainment options.

Andy Rosen can be reached at [email protected]. Subscribe to our free real estate newsletter at