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Winter Hill Homes for Sale

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  • 59 Bonair St, Somerville, MA 02145
    59 Bonair St, Somerville, MA 02145
    59 Bonair St, Somerville, MA 02145
    /36

    $1,049,000

    $50K PRICE DROP
    • 6 Beds
    • 3 Baths
    • 2,586 Sq Ft

    59 Bonair St, Somerville, MA 02145

    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

    Agent Photo

    Jose Frias

    Realty ONE Group Nest

    59 Bonair St, Somerville, MA 02145
  • 9 Dartmouth St, Somerville, MA 02145
    9 Dartmouth St, Somerville, MA 02145
    9 Dartmouth St, Somerville, MA 02145
    /42

    $1,599,999

    Open Sun 11:30AM - 1PM $50K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 3,028 Sq Ft

    9 Dartmouth St, Somerville, MA 02145

    SPECIAL 4.125% 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

    Steve Bremis Steve Bremis Realty Group

    9 Dartmouth St, Somerville, MA 02145
  • 15 Kenneson Rd, Somerville, MA 02145
    15 Kenneson Rd, Somerville, MA 02145
    15 Kenneson Rd, Somerville, MA 02145
    /18

    $1,200,000

    • 6 Beds
    • 4 Baths
    • 2,364 Sq Ft

    15 Kenneson Rd, Somerville, MA 02145

    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.

    Shane Marrion Benoit Real Estate Group ,LLC

    15 Kenneson Rd, Somerville, MA 02145
  • 232 Pearl St, Somerville, MA 02145
    232 Pearl St, Somerville, MA 02145
    232 Pearl St, 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
  • 174 Walnut St, Somerville, MA 02145
    174 Walnut St, Somerville, MA 02145
    174 Walnut St, Somerville, MA 02145
    /26

    $3,300,000

    • 11 Beds
    • 8 Baths
    • 5,921 Sq Ft

    174 Walnut St, Somerville, MA 02145

    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,

    Kirsten McEleney KM Real Estate Group

    174 Walnut St, Somerville, MA 02145
  • 7 Stickney Ave, Somerville, MA 02145
    7 Stickney Ave, Somerville, MA 02145
    7 Stickney Ave, Somerville, MA 02145
    /19

    $1,299,000

    • 7 Beds
    • 2.5 Baths
    • 3,367 Sq Ft

    7 Stickney Ave, Somerville, MA 02145

    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

    Suzanne Hickey Best Deal Realty, LLC

    7 Stickney Ave, Somerville, MA 02145
  • 400 Broadway Unit 7, Somerville, MA 02145
    400 Broadway Unit 7, Somerville, MA 02145
    400 Broadway Unit 7, Somerville, MA 02145
    /24

    $579,000

    Open Sat 11AM - 1PM
    • 1 Bed
    • 1 Bath
    • 740 Sq Ft

    400 Broadway Unit 7, Somerville, MA 02145

    Set high on Winter Hill, this oversized one-bedroom occupies the upper level of a striking Mansard Victorian and blends historic character with the updates buyers want today. Oversized windows, high ceilings, deep crown moldings, and hardwood floors give the home plenty of charm, while the natural light and city views make the space feel bright and open. The kitchen features granite countertops,

    Carlisle Group Compass

    400 Broadway Unit 7, Somerville, MA 02145
  • 106 Walnut St Unit 4, Somerville, MA 02145
    106 Walnut St Unit 4, Somerville, MA 02145
    106 Walnut St Unit 4, Somerville, MA 02145
    /29

    $685,000

    Open Sat 11AM - 12PM
    • 3 Beds
    • 2 Baths
    • 1,070 Sq Ft

    106 Walnut St Unit 4, Somerville, MA 02145

    Second-floor residence in an intimate 6-unit classic building, gut renovated in 2015 by Raid Hassan. This 3-bedroom, 2-bathroom home offers a sunlit bay window alcove, hardwood floors throughout, and generous double-door closets. The primary bedroom includes an en-suite full bath for added privacy.The location makes commuting easy. Gilman Square Station is a short walk away (0.3 miles), with

    Bilien Woldeyonas RE/MAX Real Estate Center

    106 Walnut St Unit 4, Somerville, MA 02145
  • 8 Melvin St Unit 2, Somerville, MA 02145
    8 Melvin St Unit 2, Somerville, MA 02145
    8 Melvin St Unit 2, Somerville, MA 02145
    /37

    $919,000

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,495 Sq Ft

    8 Melvin St Unit 2, Somerville, MA 02145

    OPEN HOUSE Sun 9/13 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

    Maha Krishnakumar LXTN Realty

    8 Melvin St Unit 2, Somerville, MA 02145
  • 390 Broadway Unit 35, Somerville, MA 02145
    390 Broadway Unit 35, Somerville, MA 02145
    390 Broadway Unit 35, Somerville, MA 02145
    /28

    $429,900

    Open Sat 11AM - 12:30PM
    • 1 Bed
    • 1 Bath
    • 691 Sq Ft

    390 Broadway Unit 35, Somerville, MA 02145

    Commuter’s dream in Somerville! Enjoy Green Line T access to Boston plus garage parking in a well-managed condo association. This move-in ready freshly painted third floor unit boasts an oversized bedroom, private outdoor balcony, in-unit laundry, storage space, new water heater and HVAC installed in 2025. Great for owner occupants and investors alike, this is an ideal choice for those seeking

    Evelyn Ullman Coldwell Banker Realty - Lynnfield

    390 Broadway Unit 35, Somerville, MA 02145
  • 3 Lee St, Somerville, MA 02145
    3 Lee St, Somerville, MA 02145
    3 Lee St, Somerville, MA 02145
    /15

    $1,850,000

    • 6 Beds
    • 6 Baths
    • 3,425 Sq Ft

    3 Lee St, Somerville, MA 02145

    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

    Maggie Dee + Charles Cherney Team Compass

    3 Lee St, Somerville, MA 02145
  • 390 Broadway Unit 54, Somerville, MA 02145
    390 Broadway Unit 54, Somerville, MA 02145
    390 Broadway Unit 54, Somerville, MA 02145
    /21

    $439,000

    $6K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 643 Sq Ft

    390 Broadway Unit 54, Somerville, MA 02145

    This sunny fifth-floor corner condo sits in a fantastic Winter Hill spot, putting you just minutes from Assembly Row, Davis Square, and easy transit into Boston or Cambridge. It’s been completely updated from top to bottom, so all you have to do is unpack. You’ll love the brand-new kitchen with fresh cabinets, modern counters, and new appliances, plus new flooring, fresh paint, and updated

    Gary S. Vrotsos Coldwell Banker Realty - Cambridge

    390 Broadway Unit 54, Somerville, MA 02145
  • 174 Walnut St Unit 3, Somerville, MA 02145
    174 Walnut St Unit 3, Somerville, MA 02145
    174 Walnut St Unit 3, Somerville, MA 02145
    /23

    $799,000

    $50K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,345 Sq Ft

    174 Walnut St Unit 3, Somerville, MA 02145

    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

    Kirsten McEleney KM Real Estate Group

    174 Walnut St Unit 3, Somerville, MA 02145
  • 174 Walnut St Unit 2, Somerville, MA 02145
    174 Walnut St Unit 2, Somerville, MA 02145
    174 Walnut St Unit 2, Somerville, MA 02145
    /23

    $899,000

    $91K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    174 Walnut St Unit 2, Somerville, MA 02145

    Beautiful gut-renovated 3-bed, 2-bath condominium at 174 Walnut Street offering approx. 1,532 SF of bright, single-level living. This second-floor home features an open living/dining layout, hardwood floors, oversized windows, recessed lighting, central air, and clean modern finishes throughout. The designer kitchen includes white shaker cabinetry, quartz counters, waterfall island with seating,

    Kirsten McEleney KM Real Estate Group

    174 Walnut St Unit 2, Somerville, MA 02145
  • 390 Broadway Unit 51, Somerville, MA 02145
    390 Broadway Unit 51, Somerville, MA 02145
    390 Broadway Unit 51, Somerville, MA 02145
    /35

    $525,000

    Open Sat 11AM - 12:30PM
    • 2 Beds
    • 2 Baths
    • 937 Sq Ft

    390 Broadway Unit 51, Somerville, MA 02145

    Sweeping city views set the scene for this inviting 2-bedroom, 2-bath condo located in the heart of Winter Hill in a pet-friendly professionally maintained building. Where a connected urban lifestyle meets the comfort of a welcoming retreat. The spacious living/dining combo room features hardwood flooring, a fireplace, multi-closet storage, & sliding glass doors to a private balcony—an inviting

    Rebecca Riopelle Blink Realty Group, LLC

    390 Broadway Unit 51, Somerville, MA 02145
Massachusetts Middlesex County Somerville

Real Estate & Homes for Sale in Winter Hill, Somerville

Why Live in Winter Hill
Winter Hill in Somerville is a primarily residential neighborhood north of Boston. It's known for its rich history and diverse housing options, including colonial-style homes, condos in Victorian-era buildings, and some luxury townhouses. Shops and restaurants, many of them along Broadway, are within walking distance. Leone's Sub & Pizza has been family-owned and operated since 1954. Winter Hill Brewing Company has an assortment of beverages on tap, and for dessert, there's Tipping Cow Ice Cream. Tapias Convenience Store and Taj Mahal Desi Bazaar, an Indian grocery store, are nearby. The neighborhood boasts several green spaces, such as Foss Park, which includes tennis courts, baseball diamonds and an outdoor pool. The award-winning Edward L. Leathers Community Park is known for its sustainable landscaping. Cultural highlights include the Boston Figurative Art Center and the historic Peter and Oliver Tufts House. Among the public schools is the well-regarded Somerville High School. Despite some construction and traffic, the neighborhood remains walkable with regular bus service. Massachusetts Bay Transportation Authority (MBTA) buses serve the area, and the subway is also available from the Gilman Square station. Downtown Boston is several miles away.
Learn more about living in Winter Hill

Winter Hill, Somerville, MA Home Prices vs. Nearby Neighborhoods

Winter Hill Downtown Melrose Wellington-Harrington West Somerville
Median Home Price
$756,950
$669,900
$899,000
$875,000
Median Sale Price
$762,000
-5% YoY
$614,000
-10% YoY
$906,000
+2% YoY
$852,000
-5% YoY
Avg. Price per Square Foot
$643
$564
$905
$662
Median Single Family Price
$945,000
$925,000
$1,675,000
$1,525,000
Median Condo Price
$672,000
$595,250
$850,000
$850,000
Total Active Listings
15 listings
4 listings
14 listings
7 listings
Market Conditions
3 Months of Supply
Seller's Market
4 Months of Supply
Balanced Market
4 Months of Supply
Balanced Market
3 Months of Supply
Seller's Market

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. Winter Hill has 6 parks for recreational activities.It is very dense in population with 15.0 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% of residents renting and 37% 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.
How much do you need to make to afford a house in Winter Hill?
The median home price in Winter Hill is $756,950. If you put a 20% down payment of $151,400 and had a 30-year fixed mortgage with an interest rate of 7.03%, your estimated principal and interest payment would be $4,040 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $173K 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, 02144, 02155 and 02129.
What are the most popular neighborhoods near Winter Hill, Somerville, MA?
The most popular neighborhoods near Winter Hill, Somerville, MA are Ten Hills, Prospect Hill, East Somerville, Magoun Square and Spring Hill.
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