2,529

Winter Hill Homes

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  • /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
  • /10

    $2,900

    Total Monthly Price

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

    376 Medford St Unit 1, Somerville, MA 02145

    This property at 376 Medford St features 2 bedrooms and 1 bathroom within a total of 1,000 square feet. The living room offers ample space for relaxation and is complemented by hardwood floors. The large eatin kitchen is equipped with stainless steel appliances, including a dishwasher and microwave, as well as granite countertops for durability and style. Laundry facilities are conveniently

    376 Medford St Unit 1, Somerville, MA 02145
  • /34

    $437,500

    Sold Jul 27, 2026

    326 Broadway Unit 6, Somerville, MA 02145

    • 2 Beds
    • 1 Bath
    • 696 Sq Ft
    • Built 1970

    Last Sold Summary

    • 3% Below List Price
    • $629/SF
    • 43 Days On Market

    Current Estimated Value $450,893

    Last Listing Agent John Dean Engel & Volkers Boston

    326 Broadway Unit 6, Somerville, MA 02145
    • /28

      Est $989,984

      Not Listed For Sale

      102 Gilman St, Somerville, MA 02145

      • 6 Beds
      • 2 Baths
      • 1,659 Sq Ft
      • Built 1890
      102 Gilman St, Somerville, MA 02145

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Brett Sillari Berkshire Hathaway HomeServices Commonwealth Real Estate

  • /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
  • /11

    $3,600 Plus Fees

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

    394 Broadway Unit 2, Somerville, MA 02145

    Bright, spacious, and ideally located in Somervilles sought-after Winter Hill neighborhood, this owner-occupied two-bedroom apartment offers exceptional natural light, hardwood floors, and unbeatable public transportation access.With 11 oversized windows, including a beautiful bay window, sunlight fills every room throughout the day. The apartment features approximately 1,000 square feet

    394 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 Velney Realty LLC

    59 Dartmouth St Unit A, Somerville, MA 02145
    • /14

      Est $402,983

      Not Listed For Sale

      7 Mortimer Place Unit 6, Somerville, MA 02145

      • 1 Bed
      • 1 Bath
      • 536 Sq Ft
      • Built 1970
      7 Mortimer Place Unit 6, Somerville, MA 02145

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Emily Gan Boston Value Realty

  • /42

    $1,649,900

    Open Sat 11:30AM - 1PM
    • 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
  • /20

    $2,995 Plus Fees

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    326 Broadway Unit 21, Somerville, MA 02145

    This nice 2 Bedrooms 1 Bath place in the Somerville - East Somerville area is available for 09-01-2026. Included Features are: Laundry in Basement.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

    326 Broadway Unit 21, 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 $1,171,227

    Last Listing Agent Tom Fitzpatrick Flow Realty, Inc.

    12 Montgomery Ave, Somerville, MA 02145
    • /13

      Est $482,697

      Not Listed For Sale

      280 Broadway Unit 5, Somerville, MA 02145

      • 1 Bed
      • 1 Bath
      • 635 Sq Ft
      • Built 1900
      280 Broadway Unit 5, Somerville, MA 02145

      Last Sold Summary

      • 55 Days On Market

      Last Listing Agent Joseph Pollack Redfin Corp.

  • /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
  • /20

    $4,200 Plus Fees

    • 4 Beds
    • 2 Baths
    • Condo for Rent

    8 Wesley St Unit 2, Somerville, MA 02145

    This nice 4 Bedrooms 2 Bath place in the Somerville - East Somerville area is available for 09-01-2026. Included Features are: Gas Heat, Gas Hot Water, Yard, Deck, and Laundry in Basement, Free. 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.

    8 Wesley 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 $1,114,714

    Last Listing Agent Selina Yin MacDonald Keller Williams Boston MetroWest

    20 Richdale Ave Unit 2, 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

      Last Listing Agent Rodney Sinclair J. Barrett & Company

  • /19

    $1,099,750

    • 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
  • /20

    $2,985 Plus Fees

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

    358 Broadway Unit 5, Somerville, MA 02145

    Move-In Costs Fees:First Month Rent: $2,985Security Deposit: $2,985Parking Fee: $125 / month (optional)Disclaimer: The information in this listing may have been gathered from third-party sources including the owner and/or public records. Listings are subject to errors and omissions. Encore Realty disclaims any and all representations or warranties as to the accuracy of this

    358 Broadway Unit 5, 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 $995,935

    Last Listing Agent The Paradigm Team Coldwell Banker Realty - Newton

    38 Richdale Ave, Somerville, MA 02145
    • /27

      Est $1,087,726

      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

      Last Listing Agent Hudson Santana Keller Williams Realty Boston Northwest

  • /18

    $1,099,000

    $89K PRICE DROP Pending
    • 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
  • /8

    $2,275 Plus Fees

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    111 Walnut St Unit 21, Somerville, MA 02145

    Recently updated 1 bedroom 1 bathroom with a lovely kitchen, a wall ac unit and heat and hot water included in the rent. The building has coin op laundry in the basement and is close to the new Gilman green line stop. 1 cat allowed per unit. Upfront cost- first and security.Move-In Costs Fees:First Month Rent: $2,275Security Deposit: $2,350Disclaimer: Advertised listings

    111 Walnut St Unit 21, 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
    • /40

      Est $668,322

      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

      Last Listing Agent Susan Kadilak Fiv Realty Co.

  • /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
  • /17

    $3,000

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,332 Sq Ft
    • Condo for Rent

    11 Pembroke St Unit 2, Somerville, MA 02145

    Winter Hill 2-bed condo For Rent!! Sept. 1st (or sooner!) Property Features:- Huge layout, approx. 1,332 SF of living space - Second floor unit - Tons of charm, corner lot victorian building- 2 bedrooms- Custom plantation shutters throughout - Hardwood flooring - High ceilings - Large bathroom with oversized vanity and nice linen closet- Rear porch

    11 Pembroke 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 $656,279

    Last Listing Agent Nicole Bradford Prestige Homes Real Estate, LLC

    9 Montgomery Ave Unit 1, Somerville, MA 02145
    • /29

      Est $611,583

      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

      Last Listing Agent Daniel Deychman Helix Real Estate

  • /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
  • /10

    $4,700

    Total Monthly Price

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

    86 Gilman St Unit 3, Somerville, MA 02145

    86 Gilman 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 $560,326

    Last Listing Agent Brian Fortier Joyce Lebedew Real Estate

    74 Gilman St Unit 1, Somerville, MA 02145
    • /31

      Est $1,099,714

      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

      Last Listing Agent Julie McClure Coldwell Banker Realty - Cambridge

  • /39

    $699,500

    Open Sat 11:30AM - 1PM
    • 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
  • /26

    $3,400

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,000 Sq Ft
    • Condo for Rent

    171 Walnut St Unit 2, Somerville, MA 02145

    Beds:3 BedsBaths:2 BathsIncluded:WaterPet:NegotiableLaundry:Washer/Dryer in UnitUnit Level:2

    171 Walnut St Unit 2, Somerville, MA 02145
  • /14

    $655,000

    Sold Jul 08, 2026

    60 Bradley St, Somerville, MA 02145

    • 2 Beds
    • 1.5 Baths
    • 1,142 Sq Ft
    • Built 1985

    Last Sold Summary

    • 11% Below List Price
    • $574/SF
    • 46 Days On Market

    Current Estimated Value $727,247

    Last Listing Agent Kathryn Sallis Redfin Corp.

    60 Bradley St, Somerville, MA 02145
    • /19

      Est $1,034,400

      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

      Last Listing Agent Currier, Lane & Young Compass

  • /19

    $449,000

    Open Sun 10:30AM - 12PM
    • 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
  • /10

    $3,700

    Total Monthly Price

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    358 Broadway Unit 2, Somerville, MA 02145

    In compliance with the new Massachusetts regulation—940 CMR 38.00, the move-in costs are charged as follows:First Month's Rent: $3700Last Month's Rent: $3700Security Deposit: $3700Lock & Key Fee: $N/ATotal: $11,100Move-in costs may be negotiable for well-qualified applicants. Additional fees (non-mandatory):Cat Rent: $ dependent on weight and breed Dog

    358 Broadway Unit 2, 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 $1,533,322

    Last Listing Agent Jerome Bibuld Red Tree Real Estate

    6 Mortimer Place, Somerville, MA 02145
    • /38

      Est $1,034,630

      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

      Last Listing Agent Alicia Robillard Century 21 North East

Showing Results 1 - 40, Page 1 of 18

Home Price Trends

Median Sale Price
$785,000
Median Single Family Sale Price
$997,000
Median 2 Bedroom Sale Price
$640,000
Median 1 Bedroom Sale Price
$450,750
Average Price Per Sq Ft
$650
Number of Homes for Sale
8
Last 12 months Home Sales
37
Months of Supply
2.60
Median List Price
$785,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-3%
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