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Winchester, MA Homes for Sale — Page 2 | Realty.com
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53 listings
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Homes for Sale in Winchester, MA

Homes for Sale in Winchester, MA

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24 of 53 Listings
Map

Homes for Sale in Winchester, MA

24 of 53 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #1000018

Call Thomas
  1. 189 Washington St #2 — photoPrice Reduced38Active

    $765,000

    3 bd · 2 ba · 1,643 sqft

    189 Washington St #2, Winchester, MA

    Kim Covino & Co. Team · Compass

  2. 117 Highland — photo42Active

    $1,650,000

    5 bd · 4 ba · 3,722 sqft

    117 Highland, Winchester, MA

    Dara Singleton · Better Homes and Gardens Real Estate - The Shanahan Group

  3. 17 Churchill Rd — photo37Active

    $1,749,000

    5 bd · 4 ba · 3,508 sqft

    17 Churchill Rd, Winchester, MA

    Domingo Medina · Coldwell Banker Realty - Lexington

  4. 37 Mayflower Road — photo42Active

    $3,149,000

    7 bd · 8 ba · 8,540 sqft

    37 Mayflower Road, Winchester, MA

    Kim Covino & Co. Team · Compass

  5. 19 Hancock Street — photoPrice Reduced40Active

    $2,149,000

    4 bd · 4 ba · 3,570 sqft

    19 Hancock Street, Winchester, MA

    Vita Realty Group · Compass

  6. 60 Lake St Unit E — photoPrice Reduced20Active

    $660,000

    2 bd · 2 ba · 1,190 sqft

    60 Lake St Unit E, Winchester, MA

    Shaundize Moosavizadeh · Coldwell Banker Realty - Boston

  7. 4 Churchill Road — photoPrice Reduced42Active

    $1,599,000

    4 bd · 2 ba · 2,421 sqft

    4 Churchill Road, Winchester, MA

    Kim Covino & Co. Team · Compass

  8. 24 Richardson St — photoPrice Reduced40Active

    $1,049,000

    4 bd · 3 ba · 2,411 sqft

    24 Richardson St, Winchester, MA

    Andersen Group Realty · Keller Williams Realty Boston Northwest

  9. 257 Cross Street — photo40Active

    $1,050,000

    5 bd · 3 ba · 2,801 sqft

    257 Cross Street, Winchester, MA

    Kim Covino & Co. Team · Compass

  10. 17 Russell Rd — photo25Active

    $1,098,000

    3 bd · 2 ba · 1,657 sqft

    17 Russell Rd, Winchester, MA

    Tsz Mui Kwan · Kwan Realty Inc.

  11. 96 Loring Ave — photoPrice Reduced29Active

    $919,999

    4 bd · 2 ba · 2,326 sqft

    96 Loring Ave, Winchester, MA

    Jeremy Smith · StartPoint Realty

  12. 54 Squire Road — photoPrice Reduced42Active

    $2,299,000

    4 bd · 5 ba · 4,450 sqft

    54 Squire Road, Winchester, MA

    Anthony Marino · The Marino Group Collection

  13. 18 Ridge St — photo4Active

    $3,200,000

    5 bd · 6 ba · 5,295 sqft

    18 Ridge St, Winchester, MA

    Gayle Winters & Co. Team · Compass

  14. 7 Hutchinson Road — photo42Active

    $3,450,000

    6 bd · 5 ba · 5,735 sqft

    7 Hutchinson Road, Winchester, MA

    Kim Covino & Co. Team · Compass

  15. 11 Viking Road — photo36Active

    $3,600,000

    7 bd · 8 ba · 7,429 sqft

    11 Viking Road, Winchester, MA

    Post Advisory Group · Engel & Volkers Boston

  16. 50 Holland Street — photo42Active

    $1,549,000

    3 bd · 3 ba · 2,640 sqft

    50 Holland Street, Winchester, MA

    Kim Covino & Co. Team · Compass

  17. 1 Town Way — photoPrice Reduced41Active

    $1,744,000

    3 bd · 4 ba · 3,010 sqft

    1 Town Way, Winchester, MA

    Vita Realty Group · Compass

  18. 666 Main Street #211 — photoPrice Reduced42Active

    $664,000

    2 bd · 2 ba · 1,170 sqft

    666 Main Street #211, Winchester, MA

    Elizabeth Darby · Berkshire Hathaway HomeServices Commonwealth Real Estate

  19. 47 Water Street — photoPrice Reduced30Active

    $899,000

    3 bd · 2 ba · 1,356 sqft

    47 Water Street, Winchester, MA

    The Mary Scimemi Team · Leading Edge Real Estate

  20. 247 Washington St #11 — photoPrice Reduced23Active

    $600,000

    3 bd · 3 ba · 1,494 sqft

    247 Washington St #11, Winchester, MA

    Heejeong Joo · Coldwell Banker Realty - Lexington

  21. 50 Middlesex Street #50 — photoPrice Reduced21Active

    $769,000

    2 bd · 2 ba · 1,036 sqft

    50 Middlesex Street #50, Winchester, MA

    The North Star Group · Keller Williams Realty Evolution

  22. 9 Plymouth Rd — photoPrice Reduced37Active

    $2,175,000

    5 bd · 3 ba · 4,071 sqft

    9 Plymouth Rd, Winchester, MA

    Steph Crawford Group · Real Broker MA, LLC

  23. 53 Lake Street — photoPrice Reduced42Active

    $1,025,000

    3 bd · 3 ba · 2,235 sqft

    53 Lake Street, Winchester, MA

    Kim Covino & Co. Team · Compass

  24. 6 Ivy Circle — photo36Active

    $2,100,000

    6 bd · 5 ba · 3,403 sqft

    6 Ivy Circle, Winchester, MA

    Post Advisory Group · Engel & Volkers Boston

123
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  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #1000018

    Call Thomas

    Winchester, MA community profile

    Area
    6.5 sq. mi.

    Source: HJN community data

    Winchester housing market

    October 2026 · This period is still settling

    Selling at 99.7% of asking price

    Sales here are closing essentially at asking. MLS · 16 sales · as of Oct 30, 2026

    Homes on the market · MLS, as of Oct 25, 2026

    Median list price
    $1,549,000
    Homes for sale
    57

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    2,706 sq. ft.