$980,960Average Value$686Average Price per Sq Ft5Homes For Sale
Shops, restaurants and parks on the green line in Winter Hill
Winter Hill is an artsy residential community just north of Downtown Boston. The neighborhood was named after the 120-foot hill that overlooks the area and once held a military fort that played a major part in the Revolutionary War. There’s an immense amount of history to explore here, from the early Colonial periods of America to organized crime by the Winter Hill Gang in the late 20th century. While the neighborhood consists mostly of homes, condos and apartments, there are also shops, restaurants and parks within walking distance. The neighborhood used to be more secluded from Downtown Boston, but recent improvements to the area’s public transportation have turned Winter Hill into a popular choice for commuters. “The neighborhood has changed with the new green line,” says Jack Lister, a Real Estate Salesperson with Berkshire Hathaway Verani Realty, who’s been selling homes in the area since 1967. “The route pretty much goes right through the middle of downtown.”
Beautiful colorful townhomes line the various streets of Winter Hill in Somerville.
From single to multifamily townhomes, Winter Hill has various colonial styled homes.
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Colonial-style homes starting in the $825,000s
Properties in this walkable urban neighborhood include colonial-style homes, Victorian condos and luxury townhouses. Many homes were built in the early 1900s and have since been refurbished. Older houses typically sell for $825,000 to $1.2 million, while renovated homes go for $1.75 million to $2.5 million. One- to three-bedroom converted condos and townhouses usually sell for $465,000 to $950,000.
Large Victorian Colonial-style homes line the streets of Winter Hill.
Winter Hill has many homey-looking duplexes.
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Grocery shopping at Neighborhood Produce
Neighborhood Produce is a locally owned grocer along Medford Street with fresh fruits and vegetables, pre-packaged goods and bulk items. There’s also the Taj Mahal Desi Bazaar, an Indian grocery store with a large selection of spices and fresh fish. On Pearl Street, Sarma is a popular local restaurant modeled after the traditional meyhanes of Turkey. Residents can also pick up a pizza from Leone’s Sub & Pizza or Mamma Lisa’s Pizzeria and try a New England IPA or pilsner at Winter Hill Brewing Company. For dessert, Tipping Cow Ice Cream is a family-owned shop that serves specialty flavors such as cannoli and espresso. Winter Hill is also less than a mile from Assembly Row, an outlet mall with national retailers and restaurants.
Neighborhood Produce has multiple storefronts throughout Somerville.
Buy fresh food and spices from Taj Mahal Desi Bazaar in Winter Hill.
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Winter Hill's annual artsy events
Each year the community hosts several art-centered events, including Somerville ArtBeat in July and the Somerville Holiday Flea Market in December. Both events feature local craft vendors, musicians and food trucks. Somerville also hosts rotating SomerStreets events throughout the year, which are the city's take on the internationally known Open Streets concept. The city closes select streets and opens them for events like their annual carnival, arts and music festivals and a Halloween celebration. Also nearby, the Boston Figurative Art Center offers a regular schedule of classes, including drawing as meditation.
Locals enjoy walking down to the lined booths of the venders at Gilman Park Marketplace.
Live music performances for all ages at Gilman Arts and Music Fest.
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Tennis, baseball and swimming at Foss Park
Foss Park is a moderately sized green space run by the city, which offers tennis courts, baseball diamonds and an outdoor pool. Residents can also go for a stroll or ride a bike at the award-winning Edward L. Leathers Community Park. Once a vacant lot, the park received a merit award from the Boston Society of Landscape Architects for its appearance and use of sustainable landscaping. The Hoyt-Sullivan Playground is a natural play space in a dense, urban area. On the neighborhood's eastern side, Deanna Cremin Playground has musical chimes, slides and climbing area.
Foss Park in Winter Hill also has basketball and tennis courts.
The large recreational field used by locals and Somerville students is in Foss Park.
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Standout schools in Somerville
Neighborhood kids are served by the Somerville Public Schools district. Kindergarten through eighth-grade students may attend Winter Hill Community Innovation School, which gets a C-plus from Niche. Students may then attend Somerville High School, which earns an A-minus and ranks in the top ten of Niche’s standout high schools in Massachusetts. Winter Hill is also less than 3 miles away from prestigious Harvard University and the Massachusetts Institute of Technology. “A lot of people come for the colleges here too,” says Lister. “They get here, and they love it, so they end up staying.”
Entrance to Winter Hill Community School in Somerville, MA.
Large glass windows brings natural light to the main entrance of the Somerville High School.
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From Gilman Square station to downtown
Winter Hill is an accessible urban community with walkable streets and regular bus service. The neighborhood is also served by the Gilman Square light rail station, which offers quick and easy access to Downtown Boston. The CHA Cambridge Hospital is less than 2 miles away, and Boston Logan International Airport is about 5 miles away.
Take the green line from Gilman Station in Winter Hill.
Bikers and pedestrians share the Community Path in Winter Hill on there way to the green line.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Are you familiar with the Winter Hill neighborhood?
to let others know what life in this neighborhood is like.
Crime and Safety
1 - Low Crime, 10 - High Crime
Winter Hill
US
Homicide
2
4
Sexual Assault
3
4
Assault with Weapon
3
4
Robbery
3
4
Burglary
3
4
Motor Vehicle Theft
3
4
Larceny
3
4
Crime Score
2
4
Source: WhatIsMyCrimeRisk.com
Winter Hill Demographics and Home Trends
On average, homes in Winter Hill, Somerville sell after 19 days on the market compared to the national average of 53 days. The median sale price for homes in Winter Hill, Somerville over the last 12 months is $800,000, down 7% from the median home sale price over the previous 12 months.
Inviting, corner unit one-bedroom, one-bathroom condominium offering 644 square feet of well-designed living space in the peak of Winter Hill. Built in 1978, the residence combines classic charm with efficient layout, making it an ideal choice for first-time buyers, urban professionals, or savvy investors. The thoughtful floor plan maximizes space, and includes an excellent private deck, creating
SPECIAL 3.5% FINANCING FROM SELLER (as of 12/11/25)...with 20% down and no points for owner occupants.. FANTASTIC NEW CONSTRUCTION WITH HUGE EXCLUSIVE USE ROOF DECK AND STUNNING PANORAMIC VIEWS OF BOSTON... THE BEST VALUE NEW CONSTRUCTION PENTHOUSE ONE BEDROOM IN BOSTON... INCLUDES RARE GARAGE PARKING. Stunning Sun Splashed Luxurious top flr unit w/ 9 ft clngs, skylight & custom panneled walls.
Welcome to 59 Dartmouth St, Unit A – a fully renovated 3-bedroom, 3-bath condo with a bonus room ideal for a 4th bedroom or home office. Located on a quiet residential street, this spacious unit features an open-concept floor plan, generous natural light, and modern updates throughout. Brand new kitchen and bathroom. High efficiency built (green score attached). Beautiful maple hardwood floor.
NEW YEAR, NEW HOME! This beautifully updated 2 bed/1 bath first-floor Somerville condo sits directly across from Foss Park and offers garage parking, central air, and in-unit, laundry. Fully renovated in 2015, and immaculately maintained with many updates since (below), this home boasts 9 ft ceilings, an open-concept living room, and a fully applianced stainless-steel kitchen. Bedrooms are
Spacious 2BR/2BA condo in a well-maintained building in Somerville’s ultra-convenient Winter Hill. This sunny first-floor home features an open living/dining area with hardwood floors, central air, and in-unit laundry. The kitchen offers a generous island ideal for cooking and entertaining, and both bedrooms provide comfortable, private retreats. Enjoy a deeded parking space and quick access to
Unique and peaceful 1 bedroom, 1 bath in Artist building offering 820 sq ft of living space. Just a 5-minute walk to the Green Line (Gilman Sq. Station), adjacent to the Somerville Community Bike Path, 8-minute walk to the Blue Bikes, and minutes away from Assembly Sq. and Union Sq. The apartment features In-unit washer & dryer, private porch/deck overlooking a park, brand new, energy-efficient
Located on a quiet dead street, steps away from the Gilman Square stop on the E train, This spacious 4 bed is a commuters dream. Just recently renovated with a brand new kitchen and full size washer and dryer. There is also a shared front porch and a private back porch. You will be in close proximity to Stop & Shop, Market Basket, Assembly Row, Tufts University and all the amazing new
Available 2/1/2026! Beautifully maintained Winter Hill apartment featuring classic architectural detail throughout, including original oak woodwork, moldings, and decorative fireplaces. This spacious layout offers a generously sized bedroom, an oversized living room, and a formal dining room/family room. The dining room/ family room flows into the kitchen through a large butler’s pantry, perfect
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Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
