16

Recently Sold North Main Homes

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  • /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 $1,292,116

    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 $1,065,163

    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 $2,418,554

    Last Listing Agent Jody Geany Citylight Homes LLC

    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 $1,159,867

    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 $1,173,422

    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 $1,481,248

    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 $2,291,125

    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 $1,106,122

    Last Listing Agent Michael Pierce Mystic Properties Real Estate

    76 Woodside Rd, 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 $1,065,878

    Last Listing Agent Kim Covino Compass

    9 Sylvester Ct, Winchester, MA 01890
  • /39

    $1,149,000

    Sold Jul 31, 2025

    83 Canal St Unit 85, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,300 Sq Ft
    • Built 2017

    Last Sold Summary

    • $500/SF
    • 4 Days On Market

    Last Listing Agent Mary O'Hagan Barrett Sotheby's International Realty

    83 Canal St Unit 85, 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 $1,159,867

    Last Listing Agent Nancy McLaughlin Redfin Corp.

    149 Horn Pond Brook Rd, 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 $1,070,252

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

    198 Pond St, Winchester, MA 01890
  • /40

    $1,200,000

    Sold Aug 27, 2025

    70 Woodside Rd, Winchester, MA 01890

    • 4 Beds
    • 2.5 Baths
    • 2,566 Sq Ft
    • Built 1930

    Last Sold Summary

    • $468/SF
    • 5 Days On Market

    Current Estimated Value $1,294,760

    Last Listing Agent Carolyn Vernaglia Better Homes and Gardens Real Estate - The Shanahan Group

    70 Woodside Rd, 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 $1,264,687

    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 $1,620,822

    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
$1,200,000
Median Single Family Sale Price
$1,200,000
Median Townhouse Sale Price
$999,000
Median 2 Bedroom Sale Price
$799,000
Average Price Per Sq Ft
$562
Number of Homes for Sale
7
Last 12 months Home Sales
15
Months of Supply
5.60
Median List Price
$1,212,000
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
-21%
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