North Main Homes

/38
$999,000 Pending
- 4 Beds
- 2 Baths
- 1,552 Sq Ft
76 Woodside Rd, Winchester, MA 01890

Welcome to this charming 4-bedroom, 2-bath home in desirable Winchester. Ideally located in one of the town’s most sought-after neighborhoods, this well-maintained residence offers the perfect blend of classic character and everyday comfort. The home features a bright and inviting layout with generous living spaces, hardwood floors, bookshelves and windows seats. The kitchen flows seamlessly into

Michael Pierce Mystic Properties Real Estate

76 Woodside Rd, Winchester, MA 01890
Explore North Main
/28
$2,900 total monthly price
- 2 Beds
- 1.5 Baths
- 1,000 Sq Ft
- Condo for Rent
17 Linden St Unit 17 Linden St, Winchester, MA 01890

Walk to Winchester center from this 2 bedroom, eat in kitchen with SS appliances and granite countertops, large living room, small office and 1 and 1/2 baths. Hard wood floors laundry hook up (previous tenant left washer/dryer in unit central AC gas heat. 2 off street parking spots.

17 Linden St Unit 17 Linden St, Winchester, MA 01890
/33
$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 $757,899

Last Listing Agent Rodrigo Serrano Leading Edge Real Estate

32 Clark St, Winchester, MA 01890

/39
Est $1,272,845 Not Listed For Sale

10 Chesterford Rd E, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 1,664 Sq Ft
- Built 1927
10 Chesterford Rd E, Winchester, MA 01890

Last Sold Summary
- 6% Above List Price
- $721/SF
- 3 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Kim Covino Compass

/33
$1,195,000 Open Sat 12:30PM - 2PM
- 5 Beds
- 2 Baths
- 2,331 Sq Ft
149 Horn Pond Brook Rd, Winchester, MA 01890

Picture-perfect Cape Cod single family home on a corner lot across the street from the brand new Lynch Elementary School. This special residence is much larger than it looks & has 4–5 spacious bedrooms across two levels & two full baths on each floor. Such space offers versatility with 2 beds on main level & 3 bedrooms on the upper floor. The sun-filled living room flows nicely to a charming

Nancy McLaughlin Redfin Corp.

149 Horn Pond Brook Rd, 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
Est $1,126,092 Not Listed For Sale

8 Chesterford Rd E, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 1,657 Sq Ft
- Built 1932
8 Chesterford Rd E, Winchester, MA 01890

Last Sold Summary
- 2% Above List Price
- $664/SF
- 19 Days On Market
Last Sold Price $1,100,000

Last Listing Agent Mei Zhou Coldwell Banker Realty - Andovers/Readings Regional

/35
$1,060,000 Pending
- 5 Beds
- 2.5 Baths
- 2,849 Sq Ft
62 Richardson St, Winchester, MA 01890

Stunning Two-Family home in idyllic Winchester - Ideal for multi-generational living, investors or buyers looking for a top rated School District. This home is perfectly situated on a large corner lot. Venture into Unit 1 through the all seasons porch. The kitchen offers ample cabinet space, center island, & breakfast nook. Two bedrooms on level 1, both w/ ample closet storage. Full bath w/

Frank Ventresca Strategy Street

62 Richardson St, 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 $2,338,223

Last Listing Agent Jody Geany Citylight Homes LLC

9 Norfolk Rd, Winchester, MA 01890

/42
Est $2,721,317 Not Listed For Sale

16 Ardley Place, Winchester, MA 01890
- 5 Beds
- 6 Baths
- 4,324 Sq Ft
- Built 1938
16 Ardley Place, Winchester, MA 01890

Last Sold Summary
- 3% Below List Price
- $647/SF
- 68 Days On Market
Last Sold Price $2,799,000

Last Listing Agent Ann Norberg Coldwell Banker Realty - Lexington

/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 $1,037,964

Last Listing Agent Anne Spry Barrett Sotheby's International Realty

136 Sylvester Ave, Winchester, MA 01890

/35
Est $1,919,852 Not Listed For Sale

12 Ardley Place, Winchester, MA 01890
- 3 Beds
- 4 Baths
- 2,846 Sq Ft
- Built 1940
12 Ardley Place, Winchester, MA 01890

Last Sold Summary
- 8% Above List Price
- $622/SF
- 18 Days On Market
Last Sold Price $1,771,500

Last Listing Agent Kim Covino Compass

/40
$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

35 Rumford St Unit 35, Winchester, MA 01890

/37
Est $1,369,449 Not Listed For Sale

8 Parker Rd, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 2,350 Sq Ft
- Built 1933
8 Parker Rd, Winchester, MA 01890

Last Sold Summary
- 9% Above List Price
- $536/SF
- 7 Days On Market
Last Sold Price $1,259,000

Last Listing Agent The Dovetail Group eXp Realty

/34
$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 $1,979,425

Last Listing Agent Joseph Pollack Redfin Corp.

11 Chesterford Rd E, Winchester, MA 01890

/39
Est $1,619,620 Not Listed For Sale

59 Woodside Rd, Winchester, MA 01890
- 5 Beds
- 2.5 Baths
- 2,592 Sq Ft
- Built 1930
59 Woodside Rd, Winchester, MA 01890

Last Sold Summary
- 4% Above List Price
- $598/SF
- 7 Days On Market
Last Sold Price $1,550,000

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

/32
$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 $1,273,833

Last Listing Agent Julia Xie Keller Williams Realty-Merrimack

18 Hemingway St, Winchester, MA 01890

/26
Est $1,786,208 Not Listed For Sale

7 Ardley Rd, Winchester, MA 01890
- 4 Beds
- 3.5 Baths
- 3,143 Sq Ft
- Built 1939
7 Ardley Rd, Winchester, MA 01890

Last Sold Summary
- 4% Above List Price
- $549/SF
- 75 Days On Market
Last Sold Price $1,725,000

Last Listing Agent Vantage Point Team William Raveis R.E. & Home Services

/39
$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 $2,214,292

Last Listing Agent Kim Covino Compass

4 Fairfield Place, Winchester, MA 01890

/40
Est $1,205,871 Not Listed For Sale

71 Woodside Rd, Winchester, MA 01890
- 4 Beds
- 1.5 Baths
- 2,202 Sq Ft
- Built 1927
71 Woodside Rd, Winchester, MA 01890

Last Sold Summary
- 27% Above List Price
- $431/SF
- 19 Days On Market
Last Sold Price $948,800

Last Listing Agent Kim Covino Compass

/42
$2,200,000 Sold Mar 07, 2025

6 Ardley Place, Winchester, MA 01890
- 5 Beds
- 3.5 Baths
- 3,676 Sq Ft
- Built 1940
Last Sold Summary
- 4% Below List Price
- $598/SF
- 12 Days On Market
Current Estimated Value $2,172,940

Last Listing Agent McGlynn Splaine Team Berkshire Hathaway HomeServices Commonwealth Real Estate

6 Ardley Place, Winchester, MA 01890

/42
Est $2,527,596 Not Listed For Sale

10 Norfolk Rd, Winchester, MA 01890
- 5 Beds
- 5.5 Baths
- 4,659 Sq Ft
- Built 2024
10 Norfolk Rd, Winchester, MA 01890

Last Sold Summary
- 10% Above List Price
- $494/SF
- 70 Days On Market
Last Sold Price $2,300,000

Last Listing Agent Stephen Stratford William Raveis R.E. & Home Services

/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 $1,010,403

Last Listing Agent Kim Covino Compass

9 Sylvester Ct, Winchester, MA 01890

/42
Est $1,676,830 Not Listed For Sale

64 Woodside Rd, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 2,887 Sq Ft
- Built 1931
64 Woodside Rd, Winchester, MA 01890

Last Sold Summary
- 2% Above List Price
- $572/SF
- 4 Days On Market
Last Sold Price $1,650,000

Last Listing Agent Kim Covino Compass

/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

/32
Est $1,341,093 Not Listed For Sale

114 Pond St, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 1,894 Sq Ft
- Built 1880
114 Pond St, Winchester, MA 01890

Last Sold Summary
- 3% Above List Price
- $686/SF
- 7 Days On Market
Last Sold Price $1,299,000

Last Listing Agent Jennifer Ryer Better Homes and Gardens Real Estate - The Shanahan Group

/36
$1,600,000 Sold Apr 30, 2025

24 Water St, Winchester, MA 01890
- 3 Beds
- 3.5 Baths
- 2,809 Sq Ft
- Built 2004
Last Sold Summary
- 5% Above List Price
- $570/SF
- 7 Days On Market
Current Estimated Value $1,567,501

Last Listing Agent Domingo Medina Coldwell Banker Realty - Lexington

24 Water St, Winchester, MA 01890

/42
Est $2,108,234 Not Listed For Sale

2 Fairfield Place, Winchester, MA 01890
- 5 Beds
- 2.5 Baths
- 3,746 Sq Ft
- Built 2005
2 Fairfield Place, Winchester, MA 01890

Last Sold Summary
- 11% Above List Price
- $507/SF
- 6 Days On Market
Last Sold Price $1,900,000

Last Listing Agent Kim Covino Compass

/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 $1,237,212

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

70 Woodside Rd, Winchester, MA 01890

/31
Est $1,060,814 Not Listed For Sale

47 Clark St Unit 49, Winchester, MA 01890
- 6 Beds
- 2.5 Baths
- 2,170 Sq Ft
- Built 1890
47 Clark St Unit 49, Winchester, MA 01890

Last Sold Summary
- 14% Above List Price
- $430/SF
- 4 Days On Market
Last Sold Price $932,700

Last Listing Agent Kristi Connors - Taylor Coldwell Banker Realty - Lexington

/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 $1,555,968

Last Listing Agent Kim Covino Compass

32 Woodside Rd, Winchester, MA 01890

/42
Est $1,004,898 Not Listed For Sale

30 Clark St, Winchester, MA 01890
- 2 Beds
- 1.5 Baths
- 1,370 Sq Ft
- Built 1890
30 Clark St, Winchester, MA 01890

Last Sold Summary
- 12% Above List Price
- $657/SF
- 27 Days On Market
Last Sold Price $900,000

Last Listing Agent Kim Covino Compass

/31
$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 $955,504

Last Listing Agent Anne Spry Barrett Sotheby's International Realty

79 Sylvester Ave, Winchester, MA 01890

/38
Est $923,447 Not Listed For Sale

46 Clark St, Winchester, MA 01890
- 4 Beds
- 1 Bath
- 1,616 Sq Ft
- Built 1921
46 Clark St, Winchester, MA 01890

Last Sold Summary
- 17% Above List Price
- $489/SF
- 6 Days On Market
Last Sold Price $790,000

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

/28
Est $1,019,965 Not Listed For Sale

63 Middlesex St, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 1,614 Sq Ft
- Built 1948
63 Middlesex St, Winchester, MA 01890

Last Sold Summary
- 11% Above List Price
- $567/SF
- 4 Days On Market
Last Sold Price $915,000

Last Listing Agent HMW Team HMW Real Estate, LLC

/34
Est $1,508,813 Not Listed For Sale

78 Middlesex St, Winchester, MA 01890
- 3 Beds
- 2.5 Baths
- 2,650 Sq Ft
- Built 1900
78 Middlesex St, Winchester, MA 01890

Last Sold Summary
- 5% Below List Price
- $596/SF
- 26 Days On Market
Last Sold Price $1,580,000

Last Listing Agent Marjie and Phil Gibson Sotheby's International Realty

/18
Est $1,152,071 Not Listed For Sale

44 Middlesex St Unit 46, Winchester, MA 01890
- 5 Beds
- 2 Baths
- 2,392 Sq Ft
- Built 1900
44 Middlesex St Unit 46, Winchester, MA 01890

Last Sold Summary
- 12% Above List Price
- $431/SF
- 39 Days On Market
Last Sold Price $1,030,000

Last Listing Agent Kim Covino Compass

/41
Est $1,194,937 Not Listed For Sale

61 Lake St, Winchester, MA 01890
- 4 Beds
- 1.5 Baths
- 1,985 Sq Ft
- Built 1931
61 Lake St, Winchester, MA 01890

Last Sold Summary
- 12% Above List Price
- $539/SF
- 10 Days On Market
Last Sold Price $1,070,000

Last Listing Agent Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

/41
Est $959,963 Not Listed For Sale

22 Water St, Winchester, MA 01890
- 4 Beds
- 2 Baths
- 1,932 Sq Ft
- Built 1912
22 Water St, Winchester, MA 01890

Last Sold Summary
- 8% Above List Price
- $458/SF
- 5 Days On Market
Last Sold Price $885,000

Last Listing Agent Kristin Weekley Leading Edge Real Estate

/24
Est $969,260 Not Listed For Sale

25 Hemingway St, Winchester, MA 01890
- 3 Beds
- 2 Baths
- 1,890 Sq Ft
- Built 1969
25 Hemingway St, Winchester, MA 01890

Last Sold Summary
- 1% Above List Price
- $509/SF
- 21 Days On Market
Last Sold Price $962,000

Last Listing Agent Andersen Group Realty Keller Williams Realty Boston Northwest

Showing Results 1 - 40, Page 1 of 18

Massachusetts Middlesex County Winchester North Main

Learn more about living in North Main

Home Trends in North Main, MA

On average, homes in North Main, Winchester sell after 7 days on the market compared to the national average of 54 days. The median sale price for homes in North Main, Winchester over the last 12 months is $1,464,500, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,464,500

Median Single Family Sale Price

$1,380,000

Median Townhouse Sale Price

$1,392,000

Average Price Per Sq Ft

$588

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

0.80

Median List Price

$1,359,900

Median Change From 1st List Price

Median Home Sale Price YoY Change

13%

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