$989,267Average Value$655Average Price per Sq Ft6Homes 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 30 days on the market compared to the national average of 58 days. The median sale price for homes in Winter Hill, Somerville over the last 12 months is $910,000, up 14% from the median home sale price over the previous 12 months.
A stylish, move-in-ready lifestyle condo in one of Somerville’s most vibrant urban neighborhoods. This updated home features new flooring, fresh paint, a 100% new kitchen with new countertops, new cabinets, and new stainless steel appliances, plus new AC units, an updated bathroom, and an updated electrical panel. Enjoy in-building laundry, pet-friendly living, and bike storage for added
Rare opportunity to own a well-located 4-unit property in the highly desirable Winter Hill neighborhood. Ideal for investors or developers looking to capitalize on strong rental demand and future long-term upside with rents currently below market. The property features a total of 6 bedrooms and 4 bathrooms across the four units, providing flexible living arrangements and consistent rental appeal.
A rare Somerville two-family on a quiet street in the heart of Gilman Square and at a price point that works for value-add buyers and owner-occupants alike. The 1st floor offers true flexibility: configure it as a 1 bed/1 bath or expand to 2 bed/1 bath with the existing pocket doors. Upstairs, you’ll find a spacious 4 bed/2 bath unit with both bathrooms completely gut renovated in 2015. Super
LESS THAN A QUARTER MILE TO THE GREEN LINE! WINTER HILL VICTORIAN THREE FAMILY CHARMER with growth potential! INCLUDES DETACHED TWO STORY 856 SQ FT CARRIAGE HOUSE WITH LOFT which can be a FOURTH unit ADU (incl all structural engineer plans, sprinkler plans and contractor estimate). VACANCY FOR OWNER OCCUPANT as of 6/30/26. Classic details like Bostonian moldings, medallion ceilings, original oak
Tucked away in one of Somerville’s most desired neighborhoods, this beautifully maintained home awaits for you. With four finished levels, including a walk-out lower level, this property provides flexibility for potential ADU and may present a conversion opportunity for buyers exploring a two-family layout (subject to city approvals). The home features 6 bedrooms, 3 full baths, and a bright main
Introducing a fully renovated and stabilized massive 6-unit building in the extremely desirable Winter Hill neighborhood of Somerville! This 8,060 sq foot building is nestled on a tree-lined one-way street and is directly across from the new Gilman Square green line stop and has a gross rent roll of $20,400 per month! The building has undergone extensive renovations including kitchen/bath/laundry
Discover a smart and stylish home at 60 Bradley St offering a condo alternative with a single-family feel. Located just 10 minutes from Copley Square, this property is close to train and bus lines for convenient commuting. The first floor features a fully remodeled eat-in kitchen with modern finishes, ideal for daily living and entertaining. A spacious living room with sliding patio doors opens
THE BEST VALUE IN THE BOSTON AREA!!! Spectacular unit. EXCLUSIVE USE ROOF DECK AND STUNNING PANORAMIC VIEWS OF BOSTON WITH A NON TANDEM GARAGE SPOT. INCREDIBLE FINANCING... 3.75% START RATE FOR THE FIRST YEAR. Less than a half to the Green Line!... Fantastic quality, incredible value...Stunning Sun Splashed Luxurious top flr unit has a beautiful livinig room with 9 ft clngs, skylight & custom
Well-maintained two-family property located in a desirable Somerville neighborhood. Each unit offers bright living spaces with functional layouts and great potential for rental income or owner-occupants. Features include separate utilities, ample storage, and outdoor space. Conveniently located near public transportation, restaurants, shopping, parks, and major commuting routes. Excellent
Presenting a distinguished multi-family at 7 Stickney Ave, Somerville, MA. This expansive 1920 residence offers approx. 2,600 sq ft across three levels with two generously sized, recently updated apartments. The home features seven sun-filled bedrooms plus flexible bonus rooms ideal for home offices, walk-in closets, or mudrooms. Many rooms are freshly painted, with a mix of hardwood, tile, and
Attention investors or wise first time homebuyers! Remodeled three family with second floor apartment left vacant for an owner occupant buyer (projected rent $3650, similar to 1st floor unit). Unit 1 tenants staying and lease already in place for 2027 at $3650 effective 9-1-26. Kitchens, baths and building systems have been updated to include stainless steel appliances, updated cabinets, front
Welcome to 232 Pearl street Somerville MA. Don’t miss the opportunity to own a fantastic Two-Family Home located close to Magoun Square and just steps from the new Green Line, dinning, bars and bike path. First floor (Unit 1) has 3 rooms, 1 bedroom, 1 bathroom, living room and Kitchen. Second floor (Unit 2) has 6 rooms 3 bedrooms, 1 bathroom, kitchen, dining and living room. Off-street parking
Available September 1st - Modern 2 bedroom abode between Spring and Winter Hill in Somerville. Just seconds away from the new Green Line MBTA stop set to open this summer. This units has it all, featuing Central AC, Dishwasher, New heating and hot water system (gas), intercom system to front door, new kitchen, maple cabinets, rear yard (shared), plenty of private basement storage, fully
Unit FeaturesA/C Central Air Ceramic Tiles Dishwasher Disposal Eat-in Kitchen Granite Counter Tops Hardwood Floors Laundry in Unit Modern Bath Modern Kitchen New/Renovated Bath New/Renovated Kitchen New Appliances Patio Stainless Steel Appliance(s)
Newly Renovated 3 bd 1.5 bath. Gleaming Hardwood Floors, Granite counters, and stainless steel appliances are only some of the features available in this beautiful apartment. 1 off street parking space available for $75 a month. 1 garage parking space available for $100 a month. Coin-op laundry in building. Available TODAY!310694 790
Huge 1 Bedroom, newly updated apartment for an amazing price! This penthouse style 3rd floor apartment includes cathedral ceilings, freshly refinished gleaming hard wood floors, and lots of Victorian details. You will enjoy coming home to this spacious loft style apartment with many period features inclusive of built in cabinets in the living/dining room area, hard wood floors, a skylit room, a
** Welcome to Your New Home in Vibrant Somerville! ** This astounding 2-bedroom, 1-bathroom apartment offers the perfect blend of comfort and convenience, making it an ideal choice for anyone seeking a cozy urban
** Welcome to Your New Home in Vibrant Somerville! ** This astounding 2-bedroom, 1-bathroom apartment offers the perfect blend of comfort and convenience, making it an ideal choice for anyone seeking a cozy urban
This renovated two bed is located in the Winter Hill areas of Somerville with easy access to many of the prime squares of the city including Sullivan, Union, Magoun, Ball, Davis, and Porter via walk, bike or bus. Details of the unit are as follows:-Central A/C-Eat in kitchen-Large pantries and closets-Shared yard-Fully and newly insulated-All new
Residential feel while being close to all the amenities Somerville has to offer. You’ll be just a short distance from restaurants, cafes, and shops along Broadway. Public transportation options, including nearby bus lines and the Green Line Extension, provide easy access to Boston, Cambridge, and the surrounding areas. TOTAL MOVE IN COSTS ARE NEGIOTATABLE BASED ON THE QUALIFICATIONS OF
Local Logic measures the walkability, access to public transit and bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
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