Recently Sold North Main Homes

$699,900 Sold May 30, 2025

32 Clark St, Winchester, MA 01890

• 2 Beds
• 1.5 Baths
• 1,326 Sq Ft
• Built 1890

Last Sold Summary

• $528/SF
• 4 Days On Market

Current Estimated Value $760,022

Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

$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 $1,232,664

Last Listing Agent Timothy Haynes Keller Williams Realty Signature Properties

$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 $1,003,423

Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

$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

$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 $2,381,241

Last Listing Agent Jody Geany Citylight Homes LLC

$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 $1,182,534

Last Listing Agent Nancy McLaughlin Redfin Corp.

$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 $1,057,620

Last Listing Agent Anne Spry Barrett Sotheby's International Realty

$1,635,000 Sold Jul 11, 2025

35 Rumford St Unit 35, Winchester, MA 01890

• 4 Beds
• 2.5 Baths
• 2,470 Sq Ft
• Built 2012

Last Sold Summary

• 12% Above List Price
• $662/SF
• 6 Days On Market

Last Listing Agent Elena Langlois Compass

$2,000,000 Sold Jun 02, 2025

11 Chesterford Rd E, Winchester, MA 01890

• 4 Beds
• 3.5 Baths
• 3,039 Sq Ft
• Built 1927

Last Sold Summary

• 9% Below List Price
• $658/SF
• 7 Days On Market

Current Estimated Value $1,980,699

Last Listing Agent Joseph Pollack Redfin Corp.

$1,280,000 Sold Jul 16, 2025

18 Hemingway St, Winchester, MA 01890

• 5 Beds
• 3.5 Baths
• 2,137 Sq Ft
• Built 2015

Last Sold Summary

• 6% Below List Price
• $599/SF
• 21 Days On Market

Current Estimated Value $1,320,154

Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

$2,200,000 Sold Jul 14, 2025

4 Fairfield Place, Winchester, MA 01890

• 4 Beds
• 3.5 Baths
• 3,896 Sq Ft
• Built 2016

Last Sold Summary

• 4% Below List Price
• $565/SF
• 11 Days On Market

Current Estimated Value $2,227,887

Last Listing Agent Kim Covino Compass

$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 $1,010,170

Last Listing Agent Kim Covino Compass

$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

$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 $1,279,537

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

$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 $1,550,416

Last Listing Agent Kim Covino Compass

$948,000 Sold May 29, 2025

79 Sylvester Ave, Winchester, MA 01890

• 3 Beds
• 2 Baths
• 1,469 Sq Ft
• Built 1928

Last Sold Summary

• 9% Above List Price
• $645/SF
• 5 Days On Market

Current Estimated Value $947,982

Last Listing Agent Anne Spry Barrett Sotheby's International Realty