Homes for Sale in Winter Hill, Somerville, MA

Winter Hill is a hilltop neighborhood bordered roughly by Medford Street to the south, McGrath Highway to the east, and Magoun Square to the west. The suburb has a rich history that dates all the way back to the early 18th century. There are multiple structures in the area included in the National Register of Historic Places, including the Adams-Magoun House, the Charles Adams-Woodbury Locke House, the Broadway Winter Hill Congregational Church, and the Elisha Hopkins House, among many others. A significant portion of the suburb has been developed into commercial establishments. There are plenty of restaurants, eateries, cafes, stores, and many other establishments open throughout the area. Like many other neighborhoods in Somerville, there has been significant gentrification throughout Winter Hill. Most of the available real estate in the area has been repurchased by wealthy families looking to move into the suburbs.

Homes for sale in Winter Hill is a mix of Colonial-style residences that feature various home builds. Triplexes, duplexes, townhouses, and single-family homes are all available throughout the community. Low-rise apartment buildings are also available throughout the community, adding to the overall diversity of real estate options buyers can consider in the area. Affordable home options in the neighborhood are the smaller-sized residences that feature one or two-bedroom layouts priced around $500,000 to $900,000. The larger triplexes and multi-family households are typically priced above the one million price point. The floor spaces of homes in the community range between 600 sqft to 3,800 sqft. The typical home build for properties in the area is around the early 20th century.

Market Overview

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What's To Love

You’ll love the new Green Line Extension (GLX) stop and the new conveniences brought to Winter Hill. You’ll need to book your dinner well in advance at the highly praised modern Mediterranean restaurant, Sarma! These streets are wide so resident parking isn’t too bad! Winter Hill is a well-developed historical neighborhood with lovely Colonial homes and welcoming suburban city streets. Most homes retain the classic Colonial architectural styles, and the many landmark structures all add to the suburb's overall appeal. There are plenty of public parks and schools in the area adding lots of conveniences for those looking to move here with their children. Streets are lined with restaurants and stores, providing lovely places to visit for your day-to-day needs.

What's Not To Love

Properties are a bit dated in Winter Hill, so you can expect some wear and tear when you decide to buy a home in the area. Several highways pass through the neighborhood, and traffic can get quite heavy during certain times of the day. Broadway is a little louder as it is busier with cars and buses. Side streets have a little more separation from the bustling through traffic!

Is it for me?

Who is this neighborhood for

Someone looking for slightly more affordable rental rates and home prices compared to some other high premium niches of Somerville. Winter Hill is a mixed-use neighborhood that offers convenient housing options for busy professionals working in the Greater Boston Area. The suburb is a short drive away from Downtown Boston and the many business centers near Somerville. Residents living in the community are also a short drive from MIT, Harvard University, and Tufts University. Workers at the Inner Belt industrial park and the Boston Harbor across the river will find the area quite attractive. Single-family homes in the area are relatively more affordable compared to other neighborhoods in the city. There is also a diverse selection of multi-family homes and apartment units available to buyers interested in the neighborhood. If you need help finding a home in Winter Hill, please feel free to contact our team to get started.

Find Your Home

Latest homes for sale in Winter Hill



109 Moreland St

Somerville, MA, 02145
Open House


31 Henry Street

Medford, MA, 02155
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Meet the locals

Who Lives in Somerville



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Things to do in Winter Hill

Foss Park

City Park offering excellent outdoor amenities and sports facilities.

Boston Figurative Art Center

Contemporary art gallery featuring a fantastic figure drawing and painting collection.

St Ann Church

Community church providing regular Sunday mass and various religious services.

Assembly Row

Extensive shopping center known for its big-box retail establishments located to the northeast of the neighborhood


Schools in Winter Hill

School Name
Winter Hill Community School
PK – 8
Somerville High School
9 – 12
On the map

Winter Hill Map

Around Boston Valley

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