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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
  • 326 Broadway Unit 15, Somerville, MA 02145
    326 Broadway Unit 15, Somerville, MA 02145
    326 Broadway Unit 15, Somerville, MA 02145
    /28

    $459,000

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft

    326 Broadway Unit 15, Somerville, MA 02145

    Well-maintained, bright, and sunny 2-bedroom, 1-bath condo located on the third floor of a professionally managed building. Ideally situated just steps from shops, restaurants, and public transportation, with easy access to Cambridge and downtown Boston. This inviting home features sun-filled living spaces, two generously sized bedrooms, and a full bathroom. The unit includes one designated

    Agent Photo

    Wei Wang

    WW Real Estate LLC

    326 Broadway Unit 15, Somerville, MA 02145
  • 9 Dartmouth St, Somerville, MA 02145
    9 Dartmouth St, Somerville, MA 02145
    9 Dartmouth St, Somerville, MA 02145
    /42

    $1,649,900

    • 5 Beds
    • 3 Baths
    • 3,028 Sq Ft

    9 Dartmouth St, Somerville, MA 02145

    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

    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
  • 5 Essex St, Somerville, MA 02145
    5 Essex St, Somerville, MA 02145
    5 Essex St, Somerville, MA 02145
    /18

    $1,099,000

    $89K PRICE DROP
    • 6 Beds
    • 4 Baths
    • 2,665 Sq Ft

    5 Essex St, Somerville, MA 02145

    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

    Sage Jankowitz Cambridge Sage Inc.

    5 Essex St, Somerville, MA 02145
  • 81 Gilman St, Somerville, MA 02145
    81 Gilman St, Somerville, MA 02145
    81 Gilman St, Somerville, MA 02145
    /42

    $1,529,000

    $151K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 2,396 Sq Ft

    81 Gilman St, Somerville, MA 02145

    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 Gundersheim Commonwealth Standard Realty Advisors

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

    $699,500

    • 1 Bed
    • 1 Bath
    • 798 Sq Ft

    115 Thurston St Unit I, Somerville, MA 02145

    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

    Steve Bremis Steve Bremis Realty Group

    115 Thurston St Unit I, Somerville, MA 02145
  • 390 Broadway Unit 54, Somerville, MA 02145
    390 Broadway Unit 54, Somerville, MA 02145
    390 Broadway Unit 54, Somerville, MA 02145
    /19

    $449,000

    • 1 Bed
    • 1 Bath
    • 643 Sq Ft

    390 Broadway Unit 54, Somerville, MA 02145

    Welcome to this beautifully updated fifth-floor corner unit in Winter Hill, offering the perfect blend of style, convenience, and location. Enjoy the best of Somerville living with easy access to Assembly Row, Davis Square, Union Square, Cambridge, downtown Boston, the Green Line Extension, and major commuter routes, all while coming home to a bright, comfortable retreat.Thoughtfully renovated,

    Caroline O'Shea South Shore Sotheby's International Realty

    390 Broadway Unit 54, Somerville, MA 02145
  • 73 Bonair St, Somerville, MA 02145
    73 Bonair St, Somerville, MA 02145
    73 Bonair St, Somerville, MA 02145
    /15

    $1,079,999

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    73 Bonair St, Somerville, MA 02145

    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

    Peggy Pratt Century 21 North East

    73 Bonair 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
  • 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 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

    Maha Krishnakumar LXTN Realty

    8 Melvin St Unit 2, 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
  • 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

    $825,000

    $24K 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

    $935,000

    $55K 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
  • 13 Howe St, Somerville, MA 02145
    13 Howe St, Somerville, MA 02145
    13 Howe St, Somerville, MA 02145
    /28

    $1,300,000

    • 4 Beds
    • 4 Baths
    • 2,636 Sq Ft

    13 Howe St, Somerville, MA 02145

    Three-story Victorian Italianate house in the Winter Hill Neighborhood of Somerville, with 3 residential units consisting of one 3 bed/2 bath unit, one 1 bed/1-bath unit, and 1 studio/1 bath unit. Units 2 and 3 are leased through May and August of 2027, respectively, and unit 1 will vacate at the end of August, ideal for an owner-user. The owner's unit has been updated with stainless steel

    Shane Marrion Benoit Real Estate Group ,LLC

    13 Howe St, 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 Home Prices vs. Nearby Somerville, MA Neighborhoods

Winter Hill Wellington-Harrington Downtown Melrose West Somerville
Median Home Price
$795,000
$899,000
$599,999
$899,900
Median Sale Price
$800,000
$895,000
-6% YoY
$603,000
-8% YoY
$850,000
+6% YoY
Median Single Family Price
$1,049,000
$1,675,000
$980,000
$1,525,000
Median Condo Price
$753,500
$855,000
$552,000
$849,000
Total Active Listings
7 listings
6 listings
4 listings
6 listings
Market Conditions
2 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market
4 Months of Supply
Seller's 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 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 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.
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 $795,000. If you put a 20% down payment of $159,000 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $4,100 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $176K 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, Spring Hill and Magoun Square.
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