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Winter Hill Homes for Sale

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  • 52 Bonair St, Somerville, MA 02145
    52 Bonair St, Somerville, MA 02145
    52 Bonair St, Somerville, MA 02145
    /19

    $3,000,000

    • 13 Beds
    • 6 Baths
    • 5,372 Sq Ft

    52 Bonair St, Somerville, MA 02145

    52 Bonair St is comprised of six residential units consisting of five 2-Bedroom/1-Bathroom units, and one 3-Bedroom/1-Bathroom unit. 52 Bonair St has received extensive renovations since its 2024 acquisition. All units (except for 44 Dana #1) feature brand new kitchens with quartz countertops, shaker cabinets and stainless-steel appliances, new bathrooms with new showers, vanities and flooring.

    Kelleher - Pentore Team Horvath & Tremblay

    52 Bonair St, Somerville, MA 02145
  • 54 Bonair St, Somerville, MA 02145
    54 Bonair St, Somerville, MA 02145
    54 Bonair St, Somerville, MA 02145
    /18

    $2,000,000

    • 10 Beds
    • 4 Baths
    • 3,566 Sq Ft

    54 Bonair St, Somerville, MA 02145

    54 Bonair St is comprised of a three-story residential building and contains four (4) residential units consisting of one (1), 4-Bedroom/1-Bathroom unit, one (1), 3-Bedroom/1-Bathroom unit, one (1), 2-Bedroom/1-Bathroom unit, and one (1) studio unit. The Property also offers four (4) on-site parking spaces (three in tandem). 54 Bonair Street has received extensive renovations since its 2024

    Kelleher - Pentore Team Horvath & Tremblay

    54 Bonair St, Somerville, MA 02145
  • 32 Radcliffe Rd, Somerville, MA 02145
    32 Radcliffe Rd, Somerville, MA 02145
    32 Radcliffe Rd, Somerville, MA 02145
    /41

    $1,399,000

    • 6 Beds
    • 2 Baths
    • 2,571 Sq Ft

    32 Radcliffe Rd, Somerville, MA 02145

    Charming, well maintained two family home located in the popular Winter Hill Area. Beautiful hardwood floors throughout, spacious living room and updated kitchen/dining combo. Unique features such as a walk in pantry and large closet for extra storage. Just minutes away from Assembly Row, restaurants, public transportation and more. The ease of on-site coin operated laundry & private storage on

    Kathryn Philbin Kathryn Philbin

    32 Radcliffe Rd, Somerville, MA 02145
  • 73 Bonair St, Somerville, MA 02145
    73 Bonair St, Somerville, MA 02145
    73 Bonair St, Somerville, MA 02145
    /27

    $1,299,000

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

    73 Bonair St, Somerville, MA 02145

    Welcome to Somerville. This trendy area is right in the middle of everything. Just Minutes to Tufts University, public transportation, restaurants, shopping, parks, biking trails, University and hospitals. This 2-Family home offers amazing off street parking featuring an oversized driveway fitting 5 cars comfortably. Both units are currently rented with leases. This two family home is perfect

    Kathryn Philbin Kathryn Philbin

    73 Bonair St, Somerville, MA 02145
  • 456 Medford St Unit 3, Somerville, MA 02145
    456 Medford St Unit 3, Somerville, MA 02145
    456 Medford St Unit 3, Somerville, MA 02145
    /14

    $599,900

    • 1 Bed
    • 1 Bath
    • 675 Sq Ft

    456 Medford St Unit 3, Somerville, MA 02145

    “NEWLY RENOVATED 1-Bed w/ Office & Deck — Steps from Green Line!” Enjoy this Bright & Sunny Open Concept Condominium. The Kitchen has New Stainless-Steel Appliances, Quartz Countertops, and modern cabinets. Well-designed bathroom, ample closet space, in-unit combo washer/dryer, extra basement storage, and a private back deck that leads to a shared yard. Enjoy a FABULOUS FLOOR THRU Condominium

    Tony Menounos Coldwell Banker Realty - Boston

    456 Medford St Unit 3, Somerville, MA 02145
  • 326 Broadway Unit 11, Somerville, MA 02145
    326 Broadway Unit 11, Somerville, MA 02145
    326 Broadway Unit 11, Somerville, MA 02145
    /13

    $475,000

    • 1 Bed
    • 1 Bath
    • 596 Sq Ft

    326 Broadway Unit 11, Somerville, MA 02145

    Welcome to 326 Broadway, Unit 11 – a quiet and well-maintained gem in Somerville’s charming Winter Hill neighborhood. This bright and inviting unit has been consistently rented since 2012, a testament to its strong rental appeal and unbeatable location. Currently leased through mid-2026, it offers immediate income with long-term stability. Despite its Broadway address, the unit enjoys a

    Derek Greene The Greene Realty Group

    326 Broadway Unit 11, Somerville, MA 02145
  • 24 Jackson Rd Unit 1, Somerville, MA 02145
    24 Jackson Rd Unit 1, Somerville, MA 02145
    24 Jackson Rd Unit 1, Somerville, MA 02145
    /36

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,497 Sq Ft

    24 Jackson Rd Unit 1, Somerville, MA 02145

    Discover this 2016 fully renovated first floor condo offering modern comfort in the heart of Somerville. Designed with an open concept living area in mind, a modern kitchen showcases sleek stainless steel appliances and granite countertops. The bright sun drenched family room features hardwood floors throughout and includes a generous mudroom for storage. Step outside to a private deck, perfect

    Harshini Joshi Keller Williams Realty Boston Northwest

    24 Jackson Rd Unit 1, Somerville, MA 02145
  • 59 Dartmouth St Unit A, Somerville, MA 02145
    59 Dartmouth St Unit A, Somerville, MA 02145
    59 Dartmouth St Unit A, Somerville, MA 02145
    /35

    $1,099,999

    • 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
  • 10 Stickney Ave, Somerville, MA 02145
    10 Stickney Ave, Somerville, MA 02145
    10 Stickney Ave, Somerville, MA 02145
    /42

    $1,830,000

    • 9 Beds
    • 3 Baths
    • 5,686 Sq Ft

    10 Stickney Ave, Somerville, MA 02145

    Classic triple-decker in the heart of Winter Hill! 10 Stickney Ave is a sprawling 3-family offering 5,686 sq ft of total living area, ideal for investors or owner-occupants. Each unit features oversized living/dining areas, original hardwood floors, high ceilings, and front-facing decks perfect for morning coffee or evening air. Layouts offer flexibility, charm, and function. Common areas retain

    Marc Fiore Cameron Real Estate Group

    10 Stickney Ave, Somerville, MA 02145
  • 52 Bonair St, Somerville, MA 02145
    52 Bonair St, Somerville, MA 02145
    52 Bonair St, Somerville, MA 02145
    /19

    $5,000,000

    • 23 Beds
    • 10 Baths
    • 8,938 Sq Ft

    52 Bonair St, Somerville, MA 02145

    52-54 Bonair St is comprised of 2 adjacent residential buildings on separate tax parcels. 52 Bonair contains 6 units consisting of (5) 2-Bed/1-Bath units and (1) 3-Bed/1-Bath unit. 54 Bonair contains 4 units consisting of (1) 4-Bed/1-Bath unit, (1) 3-Bed/1-Bath unit, (1) 2-Bed/1-Bath unit and 1 studio unit. 52-54 Bonair Street has received extensive renovations since its 2024 acquisition. All

    Kelleher - Pentore Team Horvath & Tremblay

    52 Bonair St, Somerville, MA 02145
  • 400 Medford St, Somerville, MA 02145
    400 Medford St, Somerville, MA 02145
    400 Medford St, Somerville, MA 02145
    /18

    $1,190,000

    • 7 Beds
    • 3 Baths
    • 2,864 Sq Ft

    400 Medford St, Somerville, MA 02145

    This rare two-family property is full of potential and ready for its next owner to add the finishing touches. Near Green Line Extension (GLX) Medford/Tufts Station, with the bus stop conveniently located right at your doorstep, the property is located in a high-demand area with excellent potential for condo conversion and long-term value. Whether you're looking to live in one unit and rent the

    Sing Cheung Central Real Estate

    400 Medford St, Somerville, MA 02145
  • 115 Highland Ave Unit 21, Somerville, MA 02143
    115 Highland Ave Unit 21, Somerville, MA 02143
    115 Highland Ave Unit 21, Somerville, MA 02143
    /16

    $635,000

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft

    115 Highland Ave Unit 21, Somerville, MA 02143

    Welcome to your dream home in the heart of Somerville. This updated two-bedroom, one full bath condo offers the perfect blend of modern convenience and classic charm. Open concept with abundant natural light that creates a warm and inviting atmosphere. Unit is move in ready! The updated kitchen features sleek counter tops, new microwave (2025), refrigerator (2022), new dishwasher (2024)and

    Maureen Kelly-Fromm RE/MAX Preferred Properties

    115 Highland Ave Unit 21, Somerville, MA 02143
  • 59 Bonair St, Somerville, MA 02145
    59 Bonair St, Somerville, MA 02145
    59 Bonair St, Somerville, MA 02145
    /36

    $1,099,000

    • 6 Beds
    • 3 Baths
    • 2,586 Sq Ft

    59 Bonair St, Somerville, MA 02145

    Tucked away in one of Somerville’s most desired neighborhoods, this beautifully maintained home awaits for youl. With four finished levels, including a walk-out lower level, this property provides flexibility for potential in-law use—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

    Jose Frias Realty ONE Group Nest

    59 Bonair St, Somerville, MA 02145
  • 7 Stickney Ave, Somerville, MA 02145
    7 Stickney Ave, Somerville, MA 02145
    7 Stickney Ave, Somerville, MA 02145
    /16

    $1,299,000

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

    7 Stickney Ave, Somerville, MA 02145

    New Price 1,299,000 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

    Suzanne Hickey Best Deal Realty, LLC

    7 Stickney Ave, Somerville, MA 02145
  • 17 Sycamore Terrace, Somerville, MA 02145
    17 Sycamore Terrace, Somerville, MA 02145
    17 Sycamore Terrace, Somerville, MA 02145
    /35

    $1,939,000

    • 10 Beds
    • 6.5 Baths
    • 4,134 Sq Ft

    17 Sycamore Terrace, Somerville, MA 02145

    ATTENTION INVESTORS...Rare to market turnkey brick 4 family in the heart of Winter Hill GENERATING OVER 13K+ PER MONTH!! ($162,240.00 ANNUALLY) The building contains a nice mixture of units including one 3 bedroom 2.5 bath, one 3 bedroom 1 bath, one 2 bedroom 2 bath and one 2 bed 1bath. All units have been renovated within the last 4 years and feature granite countertops, stainless steel

    Steve Bremis Steve Bremis Realty Group

    17 Sycamore Terrace, Somerville, MA 02145
  • 115 Thurston St Unit B, Somerville, MA 02145
    115 Thurston St Unit B, Somerville, MA 02145
    115 Thurston St Unit B, Somerville, MA 02145
    /34

    $679,900 Open Sat 11:30AM - 1:30PM

    • 2 Beds
    • 1 Bath
    • 798 Sq Ft

    115 Thurston St Unit B, Somerville, MA 02145

    NEW CONSTRUCTION AND PRICED FOR IMMEDIATE SALE WITH GREAT FINANCING! Less than half mile to two Green Line stops. Designed with a Mansard Victorian influence inside & out. Fantastic luxurious 2 BDRM unit w/ 9 ft clngs, custom panneled walls, wide plank dirty blond flrs. Great natural ligt w/ large double paned wndws. Kitchen has all stainless appliances w/ quartz counters. Fantastic Bay Window

    Steve Bremis Steve Bremis Realty Group

    115 Thurston St Unit B, 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
    /38

    $779,900 Open Sat 11:30AM - 1PM

    • 1 Bed
    • 1 Bath
    • 798 Sq Ft

    115 Thurston St Unit I, Somerville, MA 02145

    GREAT FINANCING available at 5.75%- 5/1 (30 yr am) - No Points (as of 7/16/25)! STUNNING PANORAMIC BOSTON VIEW ROOF DECK ... THE BEST VALUE NEW CONSTRUCTION PENTHOUSE ONE BEDROOM IN THE BOSTON AREA... INCLUDES RARE GARAGE PARKING. Stunning Sun Splashed Luxurious top flr unit w/ 9 ft clngs, skylight & custom panneled walls. Wide plank dirty blond flrs. Kitchen has new stainless appliances with

    Steve Bremis Steve Bremis Realty Group

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

    $1,499,000

    • 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
Massachusetts Middlesex County Somerville Winter Hill

Real Estate & Homes for Sale in Winter Hill, Somerville

Why Live in Winter Hill
Winter Hill in Somerville is an artsy residential neighborhood just north of Downtown Boston, known for its rich history and diverse housing options. The area features colonial-style homes, Victorian condos, and luxury townhouses, many of which have been refurbished with modern finishes. Residents enjoy a variety of local attractions, including shops, restaurants, and parks within walking distance. Dining options range from Leone’s Subs & Pizza to the family-owned Tipping Cow Ice Cream, while Winter Hill Brewing Company offers a selection of local brews. For groceries, Tapias Convenience Store and Taj Mahal Desi Bazaar are nearby. The neighborhood boasts several green spaces such as Foss Park, which includes tennis courts, baseball diamonds, and an outdoor pool, and the award-winning Edward L. Leathers Community Park, known for its sustainable landscaping. The Hoyt-Sullivan playground and Deanna Cremin Playground provide additional recreational opportunities. Cultural highlights include the Boston Figurative Art Center and the historic Peter and Oliver Tufts House. Winter Hill Community Innovation School serves younger students, while Somerville High School, which has a high rating, caters to older students. Despite some construction and traffic, the neighborhood remains walkable with regular bus service and the Gilman Square light rail station providing convenient access to downtown Boston. Crime rates in Winter Hill are lower than the national average, making it a relatively safe area to live.
Learn more about living in Winter Hill

Frequently Asked Questions

Is Winter Hill a good place to live?
Winter Hill is a good place to live. Winter Hill is considered fairly walkable and a biker's paradise with great transit options. Winter Hill has 6 parks for recreational activities. It is very dense in population with 18.9 people per acre and a median age of 36. The average household income is $133,633 which is above the national average. College graduates make up 56% of residents. A majority of residents in Winter Hill are renters, with 62% of residents renting and 38% 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 3 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 $350,000. If you put a 20% down payment of $70,000 and had a 30-year fixed mortgage with an interest rate of 6.72%, your estimated principal and interest payment would be $1,810 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $78K a year to afford the median home price in Winter Hill. The average household income in Winter Hill is $134K.
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 02138.
What are the most popular neighborhoods near Winter Hill, Somerville, MA?
The most popular neighborhoods near Winter Hill, Somerville, MA are Spring Hill, Prospect Hill, Ten Hills, East Somerville and Magoun Square.
Are home prices dropping in Winter Hill?
Yes, home prices in Winter Hill are down 5% in the last 12 months.

Home Trends in Winter Hill, MA

On average, homes in Winter Hill, Somerville sell after 92 days on the market compared to the national average of 70 days. The median sale price for homes in Winter Hill, Somerville over the last 12 months is $292,100, up 95% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$292,100
Median Single Family Sale Price
$292,100
Median Townhouse Sale Price
$325,000
Median 2 Bedroom Sale Price
$889,000
Median 1 Bedroom Sale Price
$651,000
Average Price Per Sq Ft
$312
Number of Homes for Sale
5
Last 12 months Home Sales
247
Months of Supply
0.20
Median List Price
$350,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
95%
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