18

Recently Sold North Main Homes

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  • /35

    $1,325,000

    Sold Aug 14, 2026

    3 Chesterford Terrace, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 2,006 Sq Ft
    • Built 1933

    Last Sold Summary

    • 2% Above List Price
    • $661/SF
    • 10 Days On Market

    Current Estimated Value $1,410,363

    Last Listing Agent Scott McNeill Compass

    3 Chesterford Terrace, Winchester, MA 01890
  • /42

    $1,330,000

    Sold Apr 14, 2026

    40 Pickering St, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,454 Sq Ft
    • Built 1870

    Last Sold Summary

    • 6% Above List Price
    • $542/SF
    • 0 Days On Market

    Current Estimated Value $1,300,556

    Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

    40 Pickering St, Winchester, MA 01890
  • /42

    $1,082,000

    Sold May 01, 2026

    38 Pickering St Unit A, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,056 Sq Ft
    • Built 1890

    Last Sold Summary

    • 8% Above List Price
    • $526/SF
    • 5 Days On Market

    Current Estimated Value $1,060,442

    Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

    38 Pickering St Unit A, Winchester, MA 01890
  • /32

    $1,380,000

    Sold Feb 26, 2026

    36 Middlesex St Unit 38, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,259 Sq Ft
    • Built 2020

    Last Sold Summary

    • 6% Above List Price
    • $611/SF
    • 6 Days On Market

    Last Listing Agent Pirani & Wile Group Gibson Sotheby's International Realty

    36 Middlesex St Unit 38, Winchester, MA 01890
  • /42

    $2,400,000

    Sold Dec 23, 2025

    9 Norfolk Rd, Winchester, MA 01890

    • 6 Beds
    • 3.5 Baths
    • 4,320 Sq Ft
    • Built 1952

    Last Sold Summary

    • $556/SF
    • 6 Days On Market

    Current Estimated Value $2,370,787

    Last Listing Agent Jody Geany Citylight Realty

    9 Norfolk Rd, Winchester, MA 01890
  • /22

    $1,641,000

    Sold Jan 30, 2026

    149 Horn Pond Brook Rd, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • Built 1954

    Last Sold Summary

    • 3% Above List Price
    • $704/SF
    • 0 Days On Market

    Current Estimated Value $1,134,921

    Last Listing Agent Nancy McLaughlin Redfin Corp.

    149 Horn Pond Brook Rd, Winchester, MA 01890
  • /36

    $1,156,000

    Sold Feb 25, 2026

    136 Sylvester Ave, Winchester, MA 01890

    • 3 Beds
    • 1.5 Baths
    • 1,608 Sq Ft
    • Built 1925

    Last Sold Summary

    • 16% Above List Price
    • $719/SF
    • 6 Days On Market

    Current Estimated Value $1,145,396

    Last Listing Agent Anne Spry Barrett Sotheby's International Realty

    136 Sylvester Ave, Winchester, MA 01890
  • /39

    $1,610,000

    Sold Jun 05, 2026

    38 Salem St Unit 40, Winchester, MA 01890

    • 5 Beds
    • 3.5 Baths
    • 3,362 Sq Ft
    • Built 2014

    Last Sold Summary

    • 7% Above List Price
    • $479/SF
    • 7 Days On Market

    Current Estimated Value $1,538,414

    Last Listing Agent Dara Singleton Better Homes and Gardens Real Estate - The Shanahan Group

    38 Salem St Unit 40, Winchester, MA 01890
  • /3

    $2,409,000

    Sold Jul 10, 2026

    49 Sheridan Cir, Winchester, MA 01890

    • 5 Beds
    • 4.5 Baths
    • 5,881 Sq Ft
    • Built 2014

    Last Sold Summary

    • $410/SF
    • 2 Days On Market

    Current Estimated Value $2,399,540

    Last Listing Agent Kim Covino Compass

    49 Sheridan Cir, Winchester, MA 01890
  • /25

    $1,080,000

    Sold May 12, 2026

    76 Woodside Rd, Winchester, MA 01890

    • 4 Beds
    • 2 Baths
    • 1,552 Sq Ft
    • Built 1920

    Last Sold Summary

    • 8% Above List Price
    • $696/SF
    • 5 Days On Market

    Current Estimated Value $1,088,550

    Last Listing Agent Michael Pierce Mystic Properties Real Estate

    76 Woodside Rd, Winchester, MA 01890
  • /28

    $1,160,000

    Sold Aug 27, 2026

    52 Salem St Unit 52, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,004 Sq Ft
    • Built 1880

    Last Sold Summary

    • 1% Above List Price
    • $579/SF
    • 7 Days On Market

    Last Listing Agent Michael Rauseo Better Homes and Gardens Real Estate - The Shanahan Group

    52 Salem St Unit 52, Winchester, MA 01890
  • /34

    $1,015,000

    Sold Dec 01, 2025

    9 Sylvester Ct, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 2,001 Sq Ft
    • Built 1963

    Last Sold Summary

    • 2% Above List Price
    • $507/SF
    • 9 Days On Market

    Current Estimated Value $1,060,820

    Last Listing Agent Kim Covino Compass

    9 Sylvester Ct, Winchester, MA 01890
  • /34

    $1,020,000

    Sold Jun 05, 2026

    149 Horn Pond Brook Rd, Winchester, MA 01890

    • 5 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • Built 1954

    Last Sold Summary

    • 21% Below List Price
    • $438/SF
    • 67 Days On Market

    Current Estimated Value $1,134,921

    Last Listing Agent Nancy McLaughlin Redfin Corp.

    149 Horn Pond Brook Rd, Winchester, MA 01890
  • /41

    $1,200,000

    Sold Aug 17, 2026

    52 Middlesex St Unit 52, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,303 Sq Ft
    • Built 1920

    Last Sold Summary

    • $521/SF
    • 8 Days On Market

    Last Listing Agent The North Star Group Keller Williams Realty Evolution

    52 Middlesex St Unit 52, Winchester, MA 01890
  • /35

    $1,660,000

    Sold Aug 07, 2026

    10 Farrow St, Winchester, MA 01890

    • 4 Beds
    • 3.5 Baths
    • 2,768 Sq Ft
    • Built 1955

    Last Sold Summary

    • 1% Above List Price
    • $600/SF
    • 6 Days On Market

    Current Estimated Value $1,644,353

    Last Listing Agent Collin Bray Century 21 Cityside

    10 Farrow St, Winchester, MA 01890
  • /24

    $1,070,000

    Sold May 20, 2026

    198 Pond St, Winchester, MA 01890

    • 4 Beds
    • 1.5 Baths
    • 1,917 Sq Ft
    • Built 1947

    Last Sold Summary

    • 7% Above List Price
    • $558/SF
    • 5 Days On Market

    Current Estimated Value $1,066,220

    Last Listing Agent The Murphy Group Lexington William Raveis R.E. & Home Services

    198 Pond St, Winchester, MA 01890
  • /35

    $1,060,000

    Sold Jun 09, 2026

    62 Richardson St, Winchester, MA 01890

    • 5 Beds
    • 2.5 Baths
    • 2,849 Sq Ft
    • Built 1870

    Last Sold Summary

    • $372/SF
    • 7 Days On Market

    Current Estimated Value $1,224,062

    Last Listing Agent Frank Ventresca Strategy Street

    62 Richardson St, Winchester, MA 01890
  • /42

    $1,549,000

    Sold Dec 15, 2025

    32 Woodside Rd, Winchester, MA 01890

    • 3 Beds
    • 2.5 Baths
    • 2,587 Sq Ft
    • Built 1933

    Last Sold Summary

    • $599/SF
    • 6 Days On Market

    Current Estimated Value $1,595,719

    Last Listing Agent Kim Covino Compass

    32 Woodside Rd, Winchester, MA 01890

Frequently Asked Questions

What is the average time to sell a house in North Main, MA?
The houses for sale in North Main, MA spend an average of 10 days on the market.
What is the number of active homes for sale in North Main, MA?
There are 7 active homes for sale in North Main, MA.

Home Price Trends

Median Sale Price
$1,325,000
Median Single Family Sale Price
$1,325,000
Median Townhouse Sale Price
$849,000
Median 2 Bedroom Sale Price
$789,000
Average Price Per Sq Ft
$579
Number of Homes for Sale
7
Last 12 months Home Sales
17
Months of Supply
4.90
Median List Price
$1,210,000
Median Change From 1st List Price
-2%
Median Home Sale Price YoY Change
-16%
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