$991,435Average Value$644Average 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 24 days on the market compared to the national average of 55 days. The median sale price for homes in Winter Hill, Somerville over the last 12 months is $785,000, down 3% from the median home sale price over the previous 12 months.
SPECIAL 3.875% FINANCING in Year One! LOVELY VACANT VICTORIAN 3 FAMILY CHARMER WITH WRAPAROUND FRONT PORCH AND PLANS FOR 4TH UNIT CARRIAGE HOUSE CONVERSION! Fantastic GROWTH potential with the DETACHED 2 STORY 856 SQ FT CARRIAGE HOUSE including LOFT which can be a FOURTH Unit ADU (seller will include structural plans, sprinkler plans & contractor estimate). LESS THAN A QUARTER MILE TO THE GREEN
SPECIAL FINANCING 5.75%, 5% DOWN on a 10/6 Loan Program (Fixed 10 yrs/ then 6 mnth adjustable!). EXCLUSIVE USE X LARGE ROOF DECK AND STUNNING PANORAMIC VIEWS OF BOSTON... MANSARD INFLUENCED NEW CONSTRUCTION WITH A NON TANDEM GARAGE SPOT. Skylight, big windows, breakfast bar and large designer bath...Less than a half to the Green Line!... Fantastic quality, incredible value...Stunning Sun Splashed
Multifamily alternative in one of Somerville’s most desired neighborhoods, this beautifully maintained Single family 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
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.
Fully gut-renovated two-family just ~0.3 mi to Gilman Square, offering a rare blend of design, flexibility, and location in one of Somerville’s most exciting neighborhoods. Thoughtfully curated with a well-balanced unit mix, Unit 1 features 2 beds/2 baths with private outdoor space and an effortless single-level layout. Unit 2 spans the upper levels with 3 beds/3 baths, offering a more expansive
Margie GundersheimCommonwealth Standard Realty Advisors
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
Rare opportunity to own a newly renovated three-family investment property in a high-demand Somerville location. 174 Walnut Street offers approx. 5,921 total gross SF across three spacious residences: a massive duplex Unit 1 with approx. 3,044 SF, 6 effective bedrooms, 3 full baths, private deck access, and excellent rental flexibility; Unit 2 with approx. 1,532 SF, 3 bedrooms, 2 full baths,
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
OPEN HOUSE Sunday Aug 2nd between 12pm-1:30pm-PRICE IMPROVEMENT-Tastefully renovated open floor concept with 3br/2 baths Condo on 2nd fl in Winter Hill area of Somerville - Features include new kitchen with new cabinets, quartz countertop, new stainless steel appliances including gas stove & microwave, master suite with attached full bath, good sized bedrooms, hardwood flooring throughout, Tile
This distinctive building offers strong curb appeal and undeniable character. Located on a tree-lined street, the property features six 1-bedroom, 1-bath units, making it an ideal addition to any investor’s portfolio. Front and back porches enhance tenant appeal. The building is equipped with central heat and hot water, providing efficiency and convenience. Paved driveway. Situated in a prime
Top-floor gut-renovated 2-bed, 2-bath condominium at 174 Walnut Street offering approx. 1,345 SF of bright, stylish living. This third-floor home features an open living/dining layout, hardwood floors, high ceilings with skylights, oversized windows, recessed lighting, central air, and clean modern finishes throughout. The kitchen includes white shaker cabinetry, quartz counters, stainless steel
3/4-bedroom, 1.5-bathroom townhouse with 3 floors of living space that offers a single-family home feel. Private front and back entrances. High-end washer/dryer in private basement. Conveniently located within 3 blocks of Gilman Square Green Line Station, Sarma restaurant, Winter Hill Brewing, and Broadway bus lines connecting Sullivan Square (Orange Line). High ceilings. Open concept kitchen.
Recently updated 1 bedroom 1 bathroom with a lovely kitchen, a wall ac unit and heat and hot water included in the rent. The building has coin op laundry in the basement and is close to the new Gilman green line stop. 1 cat allowed per unit. Upfront cost- first and security.Move-In Costs Fees:First Month Rent: $2,275Security Deposit: $2,350Disclaimer: Advertised listings
Nice 4 Bed 1 Bath available 9/1 on Gilman Ter. in SomervilleBoston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed. Photographs, videos, description and information about the properties reflect conditions at the time the information was obtained. We are pledged
This top floor is impossible to miss. A fully equipped modern kitchen with tiled back-splash, dishwasher, microwave, and disposal has recently been added to this sun-drenched 2 bed 1 bath condo. This property has hardwood floors in the main living area and carpet in the bedrooms, as well as hot water, two built-in air conditioners, and one deeded off-street parking space. Take advantage of the
Property Id: 2801227 Please note this is a three bedroom one bath apartment. Now rent by room. Location •About 0.4 miles from the Gilman Square Green Line station •Walker’s paradise with shops, a shopping center, and a grocery store within walking distance Amenities •In-unit laundry •Large windows with abundant natural light •Ample street parking with
Recently updated 1 bedroom 1 bathroom with a lovely kitchen, a wall ac unit and heat and hot water included in the rent. The building has coin op laundry in the basement and is close to the new Gilman green line stop. 1 cat allowed per unit. Upfront cost- first and security.Move-In Costs Fees:First Month Rent: $2,275Security Deposit: $2,350Disclaimer: Advertised listings
Property Id: 2801227 Please note this is a three bedroom one bath apartment. Now rent by room. Location •About 0.4 miles from the Gilman Square Green Line station •Walker’s paradise with shops, a shopping center, and a grocery store within walking distance Amenities •In-unit laundry •Large windows with abundant natural light •Ample street parking with
This nice 2 Bedrooms 2 Bath place in the Somerville - Winter Hill area is available for 09-01-2026. Included Features are: Electric heat pump Heat, Fire Places, Deck, and Laundry in Basement, Free. 1.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed.
This nice 4 Bedrooms 2 Bath place in the Somerville - East Somerville area is available for 09-01-2026. Included Features are: Gas Heat, Gas Hot Water, Yard, Deck, and Laundry in Basement, Free. 1.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed.
Bright, spacious, and ideally located in Somervilles sought-after Winter Hill neighborhood, this owner-occupied two-bedroom apartment offers exceptional natural light, hardwood floors, and unbeatable public transportation access.With 11 oversized windows, including a beautiful bay window, sunlight fills every room throughout the day. The apartment features approximately 1,000 square feet
Bright, spacious, and ideally located in Somervilles sought-after Winter Hill neighborhood, this owner-occupied two-bedroom apartment offers exceptional natural light, hardwood floors, and unbeatable public transportation access.With 11 oversized windows, including a beautiful bay window, sunlight fills every room throughout the day. The apartment features approximately 1,000 square feet
This nice 4 Bedrooms 2 Bath place in the Somerville - East Somerville area is available for 09-01-2026. Included Features are: Gas Heat, Gas Hot Water, Yard, Deck, and Laundry in Basement, Free. 1.Boston Pads is not responsible for any errors, omissions and change in price, prior sale, rent and withdrawal without notice. All information from sources reliable but not guaranteed.
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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