2,520

Winter Hill Homes

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  • /14

    $549,900

    Pending
    • 2 Beds
    • 1 Bath
    • 812 Sq Ft

    74 Gilman St Unit 4, Somerville, MA 02145

    Welcome home to 74 Gilman Street, Unit 4 — a bright, condo-quality 2-bedroom, 1-bath on the first floor of an intimate 10-unit building in the heart of Somerville's transforming Gilman Square neighborhood on a quiet one way street. Windows on 3 sides shine on gleaming hardwood floors that run throughout. Both bedrooms are generously sized to comfortably fit a bed and a full desk setup — a true

    Agent Photo

    David Last

    Last2 Development, LLC

    74 Gilman St Unit 4, Somerville, MA 02145
  • /16

    $3,500 Per Month

    • 4 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Apartment for Rent

    43 Sargent Ave Unit 2, Somerville, MA 02145

    Spacious 4-bedroom apartment ideally situated between Somerville’s Winter Hill and East Somerville neighborhoods. Offering approximately 1,200 sq ft of living space, this well-maintained home features generously sized bedrooms, wood floors, abundant closet space, and an open living and kitchen layout designed for comfortable everyday living. The updated kitchen includes stainless steel

    Agent Photo

    Sabbor Sheikh

    Coldwell Banker Realty - Boston

    43 Sargent Ave Unit 2, Somerville, MA 02145
  • /41

    $945,000

    Sold Feb 20, 2026

    59 Dartmouth St Unit A, Somerville, MA 02145

    • 4 Beds
    • 3 Baths
    • 2,081 Sq Ft
    • Built 1900

    Last Sold Summary

    • 16% Below List Price
    • $454/SF
    • 180 Days On Market

    Last Listing Agent Tal Klayman Velney Realty LLC

    59 Dartmouth St Unit A, Somerville, MA 02145
    • /33

      Est $986,017

      Not Listed For Sale

      40 Dartmouth St Unit 1, Somerville, MA 02145

      • 2 Beds
      • 2 Baths
      • 1,747 Sq Ft
      • Built 1895
      40 Dartmouth St Unit 1, Somerville, MA 02145

      Last Sold Summary

      • 6 Days On Market

  • /36

    $1,099,000

    • 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
  • /20

    $4,350 Plus Fees

    • 3 Beds
    • 1 Bath
    • Condo for Rent

    14 Stickney Ave Unit 2, Somerville, MA 02145

    EXCEPTIONAL 3 BED 1 BATH IN SOMERVILLE / WINTER HILL!STREET PARKING AVAILABLE!CALL SAMANTHA TO TOUR THIS SPACE TODAY! Boston Pads is not accountable 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

    14 Stickney Ave Unit 2, Somerville, MA 02145
  • /28

    $1,400,000

    Sold Mar 05, 2026

    12 Montgomery Ave, Somerville, MA 02145

    • 4 Beds
    • 2 Baths
    • 2,054 Sq Ft
    • Built 1915

    Last Sold Summary

    • 8% Above List Price
    • $682/SF
    • 5 Days On Market

    Current Estimated Value $1,420,099

    Last Listing Agent Tom Fitzpatrick Flow Realty, Inc.

    12 Montgomery Ave, Somerville, MA 02145
    • /32

      Not Listed For Sale

      53 Sargent Ave, Somerville, MA 02145

      • 5 Beds
      • 4 Baths
      • 3,644 Sq Ft
      • Built 1905
      53 Sargent Ave, Somerville, MA 02145

      Last Sold Summary

      • 4 Days On Market

  • /19

    $635,000

    Open Sun 1PM - 2:30PM
    • 2 Beds
    • 1 Bath
    • 905 Sq Ft

    400 Broadway Unit 3, Somerville, MA 02145

    Perched atop the historic crest of Winter Hill, this 2 bed/ 1 bath residence lives within a magnificent Mansard Victorian, a testament to the architectural grandeur of Somerville’s storied past. Inside, the heritage of the home meets modern grace. Soaring 10-foot ceilings and expansive windows bathe the open-concept living space in natural light, creating an airy sanctuary. The kitchen, finished

    Patti Brainard Compass

    400 Broadway Unit 3, Somerville, MA 02145
  • /16

    $3,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,255 Sq Ft
    • Apartment for Rent

    43 Sargent Ave Unit 1, Somerville, MA 02145

    Spacious 3-bedroom apartment ideally located between Somerville's Winter Hill and East Somerville neighborhoods. Offering over 1,250 sq ft of living space, this well-maintained home features hardwood floors, generously sized bedrooms, abundant closet space, and an open living and kitchen layout. The updated kitchen includes stainless steel appliances, ample cabinetry, and plenty of counter space.

    Agent Photo

    Sabbor Sheikh

    Coldwell Banker Realty - Boston

    43 Sargent Ave Unit 1, Somerville, MA 02145
  • /26

    $1,395,000

    Sold Jul 11, 2025

    8 Lee St Unit 2, Somerville, MA 02145

    • 5 Beds
    • 3 Baths
    • 2,258 Sq Ft
    • Built 1905

    Last Sold Summary

    • 4% Below List Price
    • $618/SF
    • 33 Days On Market

    Last Listing Agent Amy Kirsch Leading Edge Real Estate

    8 Lee St Unit 2, Somerville, MA 02145
    • /13

      Est $1,039,524

      Not Listed For Sale

      1 Richdale Ave Unit 5, Somerville, MA 02145

      • 2 Beds
      • 2 Baths
      • 1,515 Sq Ft
      • Built 2014
      1 Richdale Ave Unit 5, Somerville, MA 02145

      Last Sold Summary

      • 11 Days On Market

  • /34

    $450,000

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft

    326 Broadway Unit 6, Somerville, MA 02145

    A stylish, move-in-ready lifestyle condo in one of Somerville’s most vibrant urban neighborhoods. This updated home features new flooring, fresh paint, a 100% new kitchen with new countertops, new cabinets, and new stainless steel appliances, plus new AC units, an updated bathroom, and an updated electrical panel. Enjoy in-building laundry, pet-friendly living, and bike storage for added

    John Dean Engel & Volkers Boston

    326 Broadway Unit 6, Somerville, MA 02145
  • /20

    $4,500 Plus Fees

    • 5 Beds
    • 2 Baths
    • Condo for Rent

    151 Central St Unit 2, Somerville, MA 02145

    SpaciousRoom for rentApply NowBoston 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 to this letter and

    151 Central St Unit 2, Somerville, MA 02145
  • /39

    $1,080,000

    Sold Aug 15, 2025

    20 Richdale Ave Unit 2, Somerville, MA 02145

    • 4 Beds
    • 3.5 Baths
    • 1,750 Sq Ft
    • Built 1900

    Last Sold Summary

    • 10% Below List Price
    • $617/SF
    • 71 Days On Market

    Current Estimated Value $1,124,589

    Last Listing Agent Selina Yin MacDonald Keller Williams Boston MetroWest

    20 Richdale Ave Unit 2, Somerville, MA 02145
    • /27

      Est $1,190,822

      Not Listed For Sale

      402 Medford St Unit 2, Somerville, MA 02145

      • 3 Beds
      • 2 Baths
      • 1,690 Sq Ft
      • Built 1910
      402 Medford St Unit 2, Somerville, MA 02145

      Last Sold Summary

      • 5 Days On Market

  • /39

    $1,669,900

    $80K PRICE DROP
    • 6 Beds
    • 3 Baths
    • 3,028 Sq Ft

    9 Dartmouth St, Somerville, MA 02145

    SPECIAL 3.75% FINANCING! LESS THAN A QUARTER MILE TO THE GREEN LINE! VICTORIAN 3 FAMILY CHARMER with GROWTH potential! INCLUDES DETACHED 2 STORY 856 SQ FT CARRIAGE HOUSE W/ LOFT which can be a FOURTH unit ADU (incl structural plans, sprinkler plans & contractor est). Units 1, 2, & 3 VACANT 6/30/2026 ($3600 Unit 1 potential rent / $3200 Unit 2 potential rent/ $2700 Unit 3 potential rent). Classic

    Steve Bremis Steve Bremis Realty Group

    9 Dartmouth St, Somerville, MA 02145
  • /26

    $3,300

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 9,999 Sq Ft
    • Condo for Rent

    43 Dartmouth St Unit 2, Somerville, MA 02145

    Charming duplex 3.5 bedroom apartment located in Somerville. Step into a thoughtfully designed apartment that maximizes both style and functionality. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating an inviting space for relaxation and entertainment. One parking spot included in the rent and free laundry in the building. Commute with ease using nearby

    43 Dartmouth St Unit 2, Somerville, MA 02145
  • /34

    $975,000

    Sold Nov 05, 2025

    38 Richdale Ave, Somerville, MA 02145

    • 4 Beds
    • 2 Baths
    • 1,971 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $495/SF
    • 16 Days On Market

    Current Estimated Value $985,926

    Last Listing Agent The Paradigm Team Coldwell Banker Realty - Newton

    38 Richdale Ave, Somerville, MA 02145
    • /40

      Est $668,027

      Not Listed For Sale

      357 Medford St Unit 2, Somerville, MA 02145

      • 2 Beds
      • 1 Bath
      • 1,053 Sq Ft
      • Built 1900
      357 Medford St Unit 2, Somerville, MA 02145

      Last Sold Summary

      • 86 Days On Market

  • /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
  • /22

    $4,650

    Total Monthly Price

    • 4 Beds
    • 1 Bath
    • 1,400 Sq Ft
    • Condo for Rent

    10 Evergreen Ave Unit uni2 4-bed 1-bath, Somerville, MA 02145

    Welcome to 10 Evergreen Ave, a stunning residence located in the vibrant Winter Hill neighborhood of Somerville, Massachusetts. This spacious and sunny 4-bedroom, 7-room condo-style apartment combines modern amenities with charming vintage character, making it an ideal home for those seeking comfort and style.As you enter, you’ll be immediately impressed by the large, inviting layout that

    10 Evergreen Ave Unit uni2 4-bed 1-bath, Somerville, MA 02145
  • /19

    $762,000

    Sold Jun 26, 2026

    14 Kenneson Rd Unit A, Somerville, MA 02145

    • 2 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • Built 1980

    Last Sold Summary

    • 4% Above List Price
    • $543/SF
    • 7 Days On Market

    Current Estimated Value $732,678

    Last Listing Agent Karen Dame Century 21 North East

    14 Kenneson Rd Unit A, Somerville, MA 02145
    • /29

      Est $675,956

      Not Listed For Sale

      24 Wigglesworth St Unit 1, Somerville, MA 02145

      • 2 Beds
      • 1 Bath
      • 770 Sq Ft
      • Built 1900
      24 Wigglesworth St Unit 1, Somerville, MA 02145

      Last Sold Summary

      • 5 Days On Market

  • /15

    $3,260,000

    $100K PRICE DROP
    • 18 Beds
    • 6 Baths
    • 8,060 Sq Ft

    109 Walnut St, Somerville, MA 02145

    Introducing a fully renovated and stabilized massive 6-unit building in the extremely desirable Winter Hill neighborhood of Somerville! This 8,060 sq foot building is nestled on a tree-lined one-way street and is directly across from the new Gilman Square green line stop and has a gross rent roll of $20,400 per month! The building has undergone extensive renovations including kitchen/bath/laundry

    Lior Rozhansky Keller Williams Realty Evolution

    109 Walnut St, Somerville, MA 02145
  • /10

    $4,600

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Condo for Rent

    88 Gilman St Unit 2, Somerville, MA 02145

    88 Gilman St Unit 2, Somerville, MA 02145
  • /27

    $650,000

    Sold Jan 29, 2026

    9 Montgomery Ave Unit 1, Somerville, MA 02145

    • 2 Beds
    • 1 Bath
    • 784 Sq Ft
    • Built 1915

    Last Sold Summary

    • $829/SF
    • 27 Days On Market

    Current Estimated Value $658,481

    Last Listing Agent Nicole Bradford Prestige Homes Real Estate, LLC

    9 Montgomery Ave Unit 1, Somerville, MA 02145
    • /31

      Est $1,090,173

      Not Listed For Sale

      42 Marshall St Unit 1, Somerville, MA 02145

      • 3 Beds
      • 2 Baths
      • 1,795 Sq Ft
      • Built 1915
      42 Marshall St Unit 1, Somerville, MA 02145

      Last Sold Summary

      • 5 Days On Market

  • /14

    $689,999

    $49K PRICE DROP Pending
    • 2 Beds
    • 1.5 Baths
    • 1,142 Sq Ft

    60 Bradley St, Somerville, MA 02145

    Discover a smart and stylish home at 60 Bradley St offering a condo alternative with a single-family feel. Located just 10 minutes from Copley Square, this property is close to train and bus lines for convenient commuting. The first floor features a fully remodeled eat-in kitchen with modern finishes, ideal for daily living and entertaining. A spacious living room with sliding patio doors opens

    Kathryn Sallis Redfin Corp.

    60 Bradley St, Somerville, MA 02145
  • /10

    $2,400

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 999 Sq Ft
    • Condo for Rent

    50 Dartmouth St Unit 3, Somerville, MA 02145

    Huge 1 Bedroom, newly updated apartment for an amazing price! This penthouse style 3rd floor apartment includes cathedral ceilings, freshly refinished gleaming hard wood floors, and lots of Victorian details. You will enjoy coming home to this spacious loft style apartment with many period features inclusive of built in cabinets in the living/dining room area, hard wood floors, a skylit room, a

    50 Dartmouth St Unit 3, Somerville, MA 02145
  • /19

    $559,000

    Sold Apr 15, 2026

    74 Gilman St Unit 1, Somerville, MA 02145

    • 2 Beds
    • 2 Baths
    • 885 Sq Ft
    • Built 1920

    Last Sold Summary

    • 3% Below List Price
    • $632/SF
    • 82 Days On Market

    Current Estimated Value $561,083

    Last Listing Agent Brian Fortier Joyce Lebedew Real Estate

    74 Gilman St Unit 1, Somerville, MA 02145
    • /19

      Est $1,097,767

      Not Listed For Sale

      4 Virginia St, Somerville, MA 02145

      • 3 Beds
      • 1.5 Baths
      • 1,723 Sq Ft
      • Built 1900
      4 Virginia St, Somerville, MA 02145

      Last Sold Summary

      • 5 Days On Market

  • /39

    $699,900

    $59K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 798 Sq Ft

    115 Thurston St Unit I, Somerville, MA 02145

    NEW CONSTRUCTION...LAST UNIT LEFT...EXCLUSIVE USE ROOF DECK AND STUNNING PANORAMIC VIEWS OF BOSTON WITH A NON TANDEM GARAGE SPOT. Skylight, big windows, breakfast bar and designer bath...Less than a half to the Green Line!... Fantastic quality, incredible value...Stunning Sun Splashed Luxurious top flr unit has a beautiful livinig room with 9 ft clngs, skylight & custom paneled walls. Wide plank

    Steve Bremis Steve Bremis Realty Group

    115 Thurston St Unit I, Somerville, MA 02145
  • /15

    $5,000

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    135 Walnut St Unit 1A, Somerville, MA 02145

    Spacious and sun filled 4 bedroom, 2 bathroom apartment in a desirable Winter Hill location. This well kept unit features hardwood floors throughout, generously sized bedrooms, two full bathrooms, and a bright, open living and dining layout with great natural light.The apartment offers convenient access to major highways, shopping, restaurants, public transportation, and Assembly Row. Heat, hot

    135 Walnut St Unit 1A, Somerville, MA 02145
  • /28

    $1,515,000

    Sold Aug 29, 2025

    6 Mortimer Place, Somerville, MA 02145

    • 6 Beds
    • 3 Baths
    • 2,850 Sq Ft
    • Built 1920

    Last Sold Summary

    • 5% Below List Price
    • $532/SF
    • 8 Days On Market

    Current Estimated Value $1,546,998

    Last Listing Agent Jerome Bibuld Red Tree Real Estate

    6 Mortimer Place, Somerville, MA 02145
    • /38

      Est $1,028,845

      Not Listed For Sale

      16 Virginia St, Somerville, MA 02145

      • 4 Beds
      • 2 Baths
      • 1,511 Sq Ft
      • Built 1900
      16 Virginia St, Somerville, MA 02145

      Last Sold Summary

      • 5 Days On Market

  • /19

    $1,099,750

    Pending
    • 4 Beds
    • 3 Baths
    • 2,573 Sq Ft

    8 Sargent Ave, Somerville, MA 02145

    Contractor, builder, investor opportunity for those seeking a full-scale renovation, expansion, or teardown/redevelopment project. This expansive property offers 2573 square feet of living space, poised on a generous lot w/ample parking. Representing a significant investment opportunity in burgeoning Winter Hill, a desirable, established neighborhood still ripe with upside potential. Commuter

    Lynne Thompson Gibson Sotheby's International Realty

    8 Sargent Ave, Somerville, MA 02145
  • /13

    $3,500

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 9,999 Sq Ft
    • Condo for Rent

    15 Sargent Ave Unit 2, Somerville, MA 02145

    This property at 15 Sargent Ave features 2 bedrooms and 1 bathroom. The living room provides ample space for relaxation and entertainment. The bathroom is equipped with standard fixtures, ensuring functionality. Each bedroom offers sufficient room for furniture and personal items. Additional amenities include on-site laundry facilities for convenience.

    15 Sargent Ave Unit 2, Somerville, MA 02145
  • /18

    $455,000

    Sold Jan 30, 2026

    390 Broadway Unit 24, Somerville, MA 02145

    • 1 Bed
    • 1 Bath
    • 644 Sq Ft
    • Built 1978

    Last Sold Summary

    • 2% Above List Price
    • $707/SF
    • 5 Days On Market

    Current Estimated Value $461,755

    Last Listing Agent Gary S. Vrotsos Coldwell Banker Realty - Cambridge

    390 Broadway Unit 24, Somerville, MA 02145
    • /33

      Est $1,199,482

      Not Listed For Sale

      192 Pearl St, Somerville, MA 02145

      • 3 Beds
      • 3 Baths
      • 2,602 Sq Ft
      • Built 1900
      192 Pearl St, Somerville, MA 02145

      Last Sold Summary

      • 9 Days On Market

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$875,000
Median Single Family Sale Price
$1,099,000
Median 2 Bedroom Sale Price
$647,500
Median 1 Bedroom Sale Price
$438,788
Average Price Per Sq Ft
$662
Number of Homes for Sale
10
Last 12 months Home Sales
39
Months of Supply
3.10
Median List Price
$849,000
Median Change From 1st List Price
2%
Median Home Sale Price YoY Change
9%
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