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Winter Hill Homes for Sale

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  • /18

    $448,000

    • 1 Bed
    • 1 Bath
    • 644 Sq Ft

    390 Broadway Unit 24, Somerville, MA 02145

    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

    Gary S. Vrotsos Coldwell Banker Realty - Cambridge

    390 Broadway Unit 24, Somerville, MA 02145
  • /27

    $649,000

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft

    9 Montgomery Ave Unit 1, Somerville, MA 02145

    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

    Nicole Bradford Prestige Homes Real Estate, LLC

    9 Montgomery Ave Unit 1, Somerville, MA 02145
  • /19

    $574,000

    • 2 Beds
    • 2 Baths
    • 885 Sq Ft

    74 Gilman St Unit 1, Somerville, MA 02145

    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

    Brian Fortier Joyce Lebedew Real Estate

    74 Gilman St Unit 1, Somerville, MA 02145
  • /38

    $758,900

    • 1 Bed
    • 1 Bath
    • 798 Sq Ft

    115 Thurston St Unit I, Somerville, MA 02145

    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.

    Steve Bremis Steve Bremis Realty Group

    115 Thurston St Unit I, Somerville, MA 02145
  • /39

    $1,099,000

    • 4 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    232 Pearl St, Somerville, MA 02145

    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

    Arlindo Neto Cameron Real Estate Group

    232 Pearl St, Somerville, MA 02145
  • /41

    $999,999

    • 4 Beds
    • 3 Baths
    • 2,081 Sq Ft

    59 Dartmouth St Unit A, Somerville, MA 02145

    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.

    Tal Klayman Stuart St James, Inc.

    59 Dartmouth St Unit A, Somerville, MA 02145
  • /16

    $1,299,000

    • 7 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    7 Stickney Ave, Somerville, MA 02145

    Explore this exceptional multi-family property in Somerville, MA. This property boasts two generously sized & recently updated apartments. Numerous rooms have been newly painted. The units showcase a variety of flooring options, including elegant hardwood, stylish tile, & plush new (2022) wall-to-wall carpeting. The expansive kitchens have been updated with modern countertops & cabinets, while

    Joseph Hickey Best Deal Realty, LLC

    7 Stickney Ave, Somerville, MA 02145

Frequently Asked Questions

Is Winter Hill a good place to live?
Winter Hill is a good place to live. Winter Hill is considered very walkable and very bikeable with great transit options. Winter Hill is an urban core neighborhood with a crime score of 2, making it safer than the average neighborhood in the U.S. Winter Hill has 6 parks for recreational activities. It is fairly dense in population with 14.6 people per acre and a median age of 37. The average household income is $145,561 which is above the national average. College graduates make up 52.9% of residents. A majority of residents in Winter Hill are renters, with 63.4% of residents renting and 36.6% of residents owning their home. A local real estate agent serving Winter Hill can help you decide if this neighborhood is the right one for you. Learn more on our Winter Hill neighborhood guide.
Is Winter Hill, MA a safe neighborhood?
Winter Hill, MA is safer than the average neighborhood in the United States. It received a crime score of 2 out of 10.
How much do you need to make to afford a house in Winter Hill?
The median home price in Winter Hill is $792,000. If you put a 20% down payment of $158,400 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $3,890 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $167K a year to afford the median home price in Winter Hill. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winter Hill is $146K.
What are the best public schools in Winter Hill?
The best public schools that serve Winter Hill are:
What are the best private schools in Winter Hill?
The best private schools that serve Winter Hill are:
  • Saint Theresa School has an A Niche grade, a student teacher ratio of 12:1 and an average review score of 5.0.
What are the most popular zip codes in Winter Hill, Somerville, MA?
The most popular zip codes in Winter Hill, Somerville, MA include 02145, 02143, 02155, 02144 and 02129.
What are the most popular neighborhoods near Winter Hill, Somerville, MA?
The most popular neighborhoods near Winter Hill, Somerville, MA are Spring Hill, Ten Hills, East Somerville, Prospect Hill and Magoun Square.
Are home prices dropping in Winter Hill?
Yes, home prices in Winter Hill are down 9% in the last 12 months.

Home Trends in Winter Hill, MA

Housing Trends

Median Sale Price
$800,000
Median Single Family Sale Price
$920,000
Median 2 Bedroom Sale Price
$725,000
Median 1 Bedroom Sale Price
$500,000
Average Price Per Sq Ft
$686
Number of Homes for Sale
5
Last 12 months Home Sales
39
Months of Supply
1.50
Median List Price
$792,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-7%
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