2,502

Winter Hill Homes

Section Image
  • /19

    $559,000 Pending

    • 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 location. 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

    Brian Fortier Joyce Lebedew Real Estate

    74 Gilman St Unit 1, Somerville, MA 02145
  • /20

    $4,000 plus fees

    • 3 Beds
    • 1 Bath
    • Condo for Rent

    358 Broadway Unit 2, Somerville, MA 02145

    This nice 3 Bedrooms 1 Bath place in the Somerville - Winter Hill area is available for 09-01-2026.Boston 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

    358 Broadway 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 Stuart St James, Inc.

    59 Dartmouth St Unit A, Somerville, MA 02145
    • /28

      Est $738,685 Not Listed For Sale

      108 Gilman St Unit 1, Somerville, MA 02145

      • 2 Beds
      • 1.5 Baths
      • 797 Sq Ft
      • Built 2023
      108 Gilman St Unit 1, Somerville, MA 02145

      Last Sold Summary

      • 2% Below List Price
      • $941/SF
      • 6 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Nick Cuevas Compass

  • /42

    $1,750,000

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

    9 Dartmouth St, Somerville, MA 02145

    LESS THAN A QUARTER MILE TO THE GREEN LINE! Hard to find Winter Hill VICTORIAN THREE FAMILY CHARMER with growth potential! INCLUDES DETACHED TWO STORY 856 SQ FT CARRIAGE HOUSE WITH LOFT which can be turned into a FOURTH unit ADU (incl all structural engineer plans, sprinkler plans and contractor estimate). All the little things you love like Bostonian moldings, medallion ceilings, original oak

    Steve Bremis Steve Bremis Realty Group

    9 Dartmouth St, Somerville, MA 02145
  • /8

    $3,100 per month

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

    6 Dana St Unit 1, Somerville, MA 02145

    Welcome to this beautifully renovated 2-bedroom, 1-bathroom home in the heart of Somerville! This bright and inviting unit features gleaming hardwood floors throughout, adding warmth and character to every room. The spacious layout offers generously sized bedrooms, a comfortable living area, and plenty of natural light, making it perfect for both relaxing and entertaining.The kitchen and bath

    Carly Gundersen Atlas Group, LLC

    6 Dana St Unit 1, Somerville, MA 02145
  • /41

    $859,900 Sold May 05, 2025

    115 Thurston St Unit G, Somerville, MA 02145

    • 3 Beds
    • 2 Baths
    • 914 Sq Ft
    • Built 2023

    Last Sold Summary

    • $941/SF
    • 6 Days On Market

    Last Listing Agent Steve Bremis Steve Bremis Realty Group

    115 Thurston St Unit G, 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

      • $288/SF
      • 4 Days On Market

      Last Sold Price $1,050,000

      Last Listing Agent Rodney Sinclair J. Barrett & Company

  • /42

    $1,199,900 Pending

    • 3 Beds
    • 3.5 Baths
    • 1,678 Sq Ft

    15 Stickney Ave Unit C, Somerville, MA 02145

    AWESOME NEW CONSTRUCTION LUXURY THREE BEDROOM DETACHED COTTAGE...JUST A BLOCK FROM THE GREEN LINE! I hate to say cute and cozy but... if you have a hankering for the single family lifestyle, look no further. Fantastic Three Level Cottage with 3 bdrms, 3.5 bths, ONE CAR NON TNDM PARKING. EXCL USE PATIO AND YARD AREA. Open Living - Kitchen area has a gas log fireplace, softly stained wide plank

    Steve Bremis Steve Bremis Realty Group

    15 Stickney Ave Unit C, Somerville, MA 02145
  • /17

    $3,700 plus fees

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    358 Broadway Unit 6, Somerville, MA 02145

    This nice 2 Bedrooms 1 Bath place in the Somerville - Winter Hill area is available for 09-01-2026. Included Features are: Deck, and Laundry in Common Area.Boston 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

    358 Broadway Unit 6, 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 $1,318,141

    Last Listing Agent Tom Fitzpatrick Flow Realty, Inc.

    12 Montgomery Ave, Somerville, MA 02145
    • /13

      Est $949,295 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

      • 1% Below List Price
      • $634/SF
      • 11 Days On Market

      Last Sold Price $960,000

      Last Listing Agent Holly Almgren Coldwell Banker Realty - Cambridge

  • /26

    $999,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,806 Sq Ft

    41 Sargent Ave Unit 2, Somerville, MA 02145

    Situated on a quiet side street with two coveted, deeded off-street parking spaces, this beautifully renovated upper level Condo features open concept living and exceptional craftsmanship with soaring 9'6" ceilings, lovely crown moldings and handsome oak flooring.The stunning chef's kitchen wiith quartz counters, large island, SS appliances and abundance of custom cabinetry seamlessly adjoins the

    The Walsh Team And Partners William Raveis R.E. & Home Services

    41 Sargent Ave Unit 2, Somerville, MA 02145
  • /10

    $5,450 per month

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Apartment for Rent

    14 Stickney Ave Unit 1, Somerville, MA 02145

    Location! Location! Location! Just a ~5-minute walk to the new Gilman Square Green Line station.Beautiful condo-quality 4-bedroom in Somerville featuring spacious, comfortable bedrooms and a modern open floor plan. The home has undergone a complete high-end renovation from floor to ceiling, including an incredible kitchen and updated baths. Enjoy in-unit laundry, central air with efficient gas

    Shane Marrion Benoit Real Estate Group ,LLC

    14 Stickney 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
    • /40

      Est $651,923 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

      • 2% Above List Price
      • $608/SF
      • 86 Days On Market

      Last Sold Price $640,000

      Last Listing Agent Susan Kadilak Fiv Realty Co.

  • /40

    $1,299,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,076 Sq Ft

    15 Stickney Ave Unit A, Somerville, MA 02145

    Seeing is believing! STUNNING NEW LUXURY CONSTRUCTION...JUST A BLOCK FROM THE GREEN LINE... with NON TANDEM PARKING. Exceptional Quality and Design! A sunny spacious modern escape that's perfect for entertaining. Fantastic Open Fireplace Living Room with hardwood floors and an abundance of large beautifully appointed Black Composite Marvin Windows throughout. Delightful well thought out 3 bedroom

    Steve Bremis Steve Bremis Realty Group

    15 Stickney Ave Unit A, Somerville, MA 02145
  • /20

    $3,475 plus fees

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    358 Broadway Unit 5, Somerville, MA 02145

    This nice 2 Bedrooms 1 Bath place in the Somerville - Winter Hill area is available for 09-01-2026. Included Features are: Deck. 1.Boston 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

    358 Broadway Unit 5, 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 $1,095,198

    Last Listing Agent Selina Yin MacDonald Keller Williams Boston MetroWest

    20 Richdale Ave Unit 2, Somerville, MA 02145
    • /29

      Est $652,540 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

      • 1% Below List Price
      • $857/SF
      • 5 Days On Market

      Last Sold Price $660,000

      Last Listing Agent Daniel Deychman Helix Real Estate

  • /39

    $1,369,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,930 Sq Ft

    52 Thurston St Unit 3, Somerville, MA 02145

    Welcome to the beautifully appointed and sophisticated living at the transformed St. Ann's Convent. The exclusive use 330+ sf rooftop deck in Somerville, not unheard of but something to see! Your foyer is it's own living space outside your front door. Once you enter, the space is breath taking with open living space, hardwood flooring, custom built-ins, fire placed living room, custom metal

    Alice Sahakian Century 21 North East

    52 Thurston St Unit 3, Somerville, MA 02145
  • /8

    $2,825 per month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Condo for Rent

    326 Broadway Unit 21, Somerville, MA 02145

    This top floor is impossible to miss. A fully equipped modern kitchen with tiled back-splash, dishwasher, microwave, and disposal has recently been added to this sun-drenched 2 bed 1 bath condo. This property has hardwood floors in the main living area and carpet in the bedrooms, as well as hot water, two built-in air conditioners, and one deeded off-street parking space. Take advantage of the

    Jarrett Lau Profitable Properties Boston LLC

    326 Broadway Unit 21, Somerville, MA 02145
  • /19

    $1,099,000 Sold Apr 17, 2025

    171 Walnut St Unit 173, Somerville, MA 02145

    • 4 Beds
    • 2.5 Baths
    • 2,991 Sq Ft
    • Built 2015

    Last Sold Summary

    • $367/SF
    • 3 Days On Market

    Last Listing Agent Jerome Bibuld Red Tree Real Estate

    171 Walnut St Unit 173, Somerville, MA 02145
    • /31

      Est $1,039,054 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

      • 6% Below List Price
      • $613/SF
      • 5 Days On Market

      Last Sold Price $1,100,000

      Last Listing Agent Julie McClure Coldwell Banker Realty - Cambridge

  • /41

    $1,399,900 Pending

    • 4 Beds
    • 3.5 Baths
    • 2,161 Sq Ft

    15 Stickney Ave Unit B, Somerville, MA 02145

    EXCEPTIONAL IN ITS DESIGN...NEW LUXURY CONSTRUCTION ...JUST A BLOCK FROM THE GREEN LINE... with NON TANDEM PARKING. Discover a stunning spacious modern escape with custom finishes throughout. A sunny spacious modern oasis that's perfect for entertaining. Fantastic Incredibly Sunny Open Fireplace Living Room with hardwood wide plank floors and an abundance of large beautifully appointed Black

    Steve Bremis Steve Bremis Realty Group

    15 Stickney Ave Unit B, Somerville, MA 02145
  • /10

    $1,100 plus fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    43 Bradley St Unit 2, Somerville, MA 02145

    Property Id: 2416731Please read the full description before reaching out.This spacious two-floor unit (approximately 2,400 sq ft) offers comfortable shared living. Conveniently located 0.4 miles from the Gilman Square Green Line station. Walker’s paradise, with walking distance to a shopping center and grocery store. Amenities include in-unit laundry, ample street parking with a

    43 Bradley 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 $976,403

    Last Listing Agent The Paradigm Team Coldwell Banker Realty - Newton

    38 Richdale Ave, Somerville, MA 02145
    • /16

      Est $667,843 Not Listed For Sale

      9 James St Unit 1, Somerville, MA 02145

      • 2 Beds
      • 2 Baths
      • 1,100 Sq Ft
      • Built 1905
      9 James St Unit 1, Somerville, MA 02145

      Last Sold Summary

      • $609/SF
      • 5 Days On Market

      Last Sold Price $670,000

      Last Listing Agent Stefanie Clifford Keller Williams Realty Boston Northwest

  • /39

    $749,900

    • 1 Bed
    • 1 Bath
    • 798 Sq Ft

    115 Thurston St Unit I, Somerville, MA 02145

    FANTASTIC NEW CONSTRUCTION WITH HUGE EXCLUSIVE USE ROOF DECK AND STUNNING PANORAMIC VIEWS OF BOSTON. GREAT FINANCING... 5.5% on a 10/6 (fixed for 10 yrs @ 5.5% , turns into a 6 month adjustable) - No Points... Less than a half to the Green Line!... Also includes RARE EXCLUSIVE GARAGE PARKING SPOT. Fantastic quality, incredible value... Stunning Sun Splashed Luxurious top flr unit w/ 9 ft clngs,

    Steve Bremis Steve Bremis Realty Group

    115 Thurston St Unit I, Somerville, MA 02145
  • /14

    $2,400 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Apartment for Rent

    12 Lee St Unit 3, Somerville, MA 02145

    6 MINUTES WALKING TO GILMAN SQUARE. 9 MINUTES DRIVE TO TUFT UNIVERSITY. Available from May 1, 2026. This THIRD FLOOR apartment has TWO large Bedrooms, large Living Room, Large Dinning cum Kitchen area and one Bathroom. The kitchen has gas stove & refrigerator. NO dishwasher. The apt has beautiful hardwood floors and the HEATING system is all ELECTRIC. No Storage allowed in the basement, This unit

    Susan Chopra Homes Realty

    12 Lee St Unit 3, Somerville, MA 02145
  • /40

    $900,000 Sold May 21, 2025

    115 Thurston St Unit H, Somerville, MA 02145

    • 3 Beds
    • 2 Baths
    • 1,018 Sq Ft
    • Built 2023

    Last Sold Summary

    • $884/SF
    • 14 Days On Market

    Last Listing Agent Steve Bremis Steve Bremis Realty Group

    115 Thurston St Unit H, Somerville, MA 02145
    • /31

      Est $526,644 Not Listed For Sale

      369 Medford St Unit 3, Somerville, MA 02145

      • 2 Beds
      • 1 Bath
      • 731 Sq Ft
      • Built 1900
      369 Medford St Unit 3, Somerville, MA 02145

      Last Sold Summary

      • 5% Above List Price
      • $684/SF
      • 153 Days On Market

      Last Sold Price $500,000

      Last Listing Agent Kevin Bergin RE/MAX

  • /15

    $1,079,999 Open Sat 1PM - 2:30PM

    • 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
  • /8

    $4,599 total monthly price

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

    110 Walnut St Unit 1, Somerville, MA 02145

    Welcome to this spacious 4-bedroom, 2-bath apartment located on a quiet residential street in Newton. With approximately 2,800 square feet of thoughtfully designed living space, this unit offers a comfortable and functional layout.Enjoy a spacious living area filled with natural light, a well-equipped kitchen, and generously sized bedrooms. Laundry is conveniently located in the building

    110 Walnut St Unit 1, Somerville, MA 02145
  • /13

    $800,000 Sold May 09, 2025

    28 Dana St Unit 1, Somerville, MA 02145

    • 2 Beds
    • 3 Baths
    • 1,898 Sq Ft
    • Built 1910

    Last Sold Summary

    • 3% Above List Price
    • $421/SF
    • 22 Days On Market

    Current Estimated Value $841,866

    Last Listing Agent Darin Thompson Stuart St James, Inc.

    28 Dana St Unit 1, Somerville, MA 02145
    • /19

      Est $1,044,908 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

      • 6% Above List Price
      • $573/SF
      • 5 Days On Market

      Last Sold Price $988,000

      Last Listing Agent Currier, Lane & Young Compass

  • /27

    $320,000 Pending

    • 1 Bed
    • 1 Bath
    • 429 Sq Ft

    7 Mortimer Place Unit 2, Somerville, MA 02145

    Convenience and efficiency are key in this perfectly located studio condo situated between Winter Hill, Assembly Square, Spring Hill and East Somerville. Featuring gleaming hardwood floors, a well-appointed kitchen with granite countertops, coffee bar and stainless steel appliances, plenty of closet space and a murphy bed for flexible use of the living area, this efficient unit punches well above

    Paul Reeves Coldwell Banker Realty - Newton

    7 Mortimer Place Unit 2, Somerville, MA 02145
  • /12

    $2,500 per month

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

    116 Sycamore St Unit 26, Somerville, MA 02145

    Well-maintained one-bedroom, one-bath apartment with hardwood floors throughout, a flexible layout, and one off-street parking space included, ideally located near the Gilman Square Green Line station in Somerville. The spacious living room features air conditioning and provides enough room for both a comfortable living area and a work-from-home setup or dining area. The kitchen, located just off

    Jason Niles Coldwell Banker Realty - Framingham

    116 Sycamore St Unit 26, 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 $650,179

    Last Listing Agent Nicole Bradford Prestige Homes Real Estate, LLC

    9 Montgomery Ave Unit 1, Somerville, MA 02145
    • /38

      Est $999,121 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

      • $662/SF
      • 5 Days On Market

      Last Sold Price $1,000,000

      Last Listing Agent Alicia Robillard Century 21 North East

Showing Results 1 - 40, Page 1 of 18

Home Trends in Winter Hill, MA

Housing Trends

Median Sale Price
$867,450
Median Single Family Sale Price
$1,099,000
Median 2 Bedroom Sale Price
$725,000
Median 1 Bedroom Sale Price
$500,000
Average Price Per Sq Ft
$677
Number of Homes for Sale
3
Last 12 months Home Sales
42
Months of Supply
0.90
Median List Price
$848,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
7%
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