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60+ Homes for Sale in Winchester, MA

66 results

Property at 7 Wainwright Road #113, Winchester, MA 01890
1 / 42
Active
Price

$1,999,000

7 Wainwright Road #113, Winchester, MA 01890

4 bds
|
3.5 ba
|
3640 sqft
MLS® 73556476Condominium
Compass - Kim Covino & Co. Team
Property at 39 Henry Street, Winchester, MA 01890
1 / 23
Active
New
Open

$899,000

39 Henry Street, Winchester, MA 01890

3 bds
|
1 ba
|
1313 sqft
MLS® 73585414Single Family Residence
Coldwell Banker Realty - Belmont - Kelly Batti
Property at 200 Swanton St #T14, Winchester, MA 01890
1 / 26
Active
Price

$319,000

200 Swanton St #T14, Winchester, MA 01890

1 bds
|
1 ba
|
602 sqft
MLS® 73580409Condominium
The Synergy Group - The Synergy Group
Property at 257 Cross Street, Winchester, MA 01890
1 / 40
Active

$1,050,000

257 Cross Street, Winchester, MA 01890

5 bds
|
2.5 ba
|
2801 sqft
MLS® 73571418Single Family Residence
Compass - Kim Covino & Co. Team
Property at 24 Richardson St, Winchester, MA 01890
1 / 40
Active
Price
Open

$1,069,000

24 Richardson St, Winchester, MA 01890

4 bds
|
2.5 ba
|
2411 sqft
MLS® 73571480Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty

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Property at 26 Mayflower Road, Winchester, MA 01890
1 / 42
Active
Open

$1,950,000

26 Mayflower Road, Winchester, MA 01890

5 bds
|
4 ba
|
3371 sqft
MLS® 73584117Single Family Residence
The Simply Sold Realty Co. - Nicole M. Condon
Property at 96 Loring Ave, Winchester, MA 01890
1 / 29
Active
Price

$919,999

96 Loring Ave, Winchester, MA 01890

4 bds
|
2 ba
|
2326 sqft
MLS® 73561829Single Family Residence
StartPoint Realty - Jeremy Smith
Property at 9 Priscilla Ln, Winchester, MA 01890
1 / 31
Active
Open

$1,325,000

9 Priscilla Ln, Winchester, MA 01890

4 bds
|
2 ba
|
1922 sqft
MLS® 73579538Single Family Residence
Compass - Robert Del Greco
Property at 666 Main Street #211, Winchester, MA 01890
1 / 42
Active
Price

$685,000

666 Main Street #211, Winchester, MA 01890

2 bds
|
2 ba
|
1170 sqft
MLS® 73553517Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 666 Main Street #217, Winchester, MA 01890
1 / 41
Active

$700,000

666 Main Street #217, Winchester, MA 01890

2 bds
|
2 ba
|
1240 sqft
MLS® 73581469Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 276 High Street, Winchester, MA 01890
1 / 36
Active
Price

$2,195,000

276 High Street, Winchester, MA 01890

5 bds
|
3.5 ba
|
5006 sqft
MLS® 73496396Single Family Residence
Compass - Kim Covino & Co. Team
Property at 6 Ivy Circle, Winchester, MA 01890
1 / 36
Active
Open

$2,100,000

6 Ivy Circle, Winchester, MA 01890

6 bds
|
4 ba
|
3403 sqft
MLS® 73510713Single Family Residence
Engel & Volkers Boston - Post Advisory Group
Property at 15 Vinson Circle, Winchester, MA 01890
1 / 42
Active
New

$18,000,000

15 Vinson Circle, Winchester, MA 01890

6 bds
|
6.5 ba
|
10000 sqft
MLS® 73585235Single Family Residence
The Marino Group Collection - Anthony Marino
Property at 4 Stone Ave, Winchester, MA 01890
1 / 38
Active
Open

$1,195,000

4 Stone Ave, Winchester, MA 01890

3 bds
|
1.5 ba
|
2239 sqft
MLS® 73582171Single Family Residence
The Synergy Group - The Synergy Group
Property at 60 Lake St #E, Winchester, MA 01890
1 / 20
Active
Price
Open

$660,000

60 Lake St #E, Winchester, MA 01890

2 bds
|
1.5 ba
|
1190 sqft
MLS® 73572854Condominium
Coldwell Banker Realty - Boston - Shaundize Moosavizadeh
Property at 54 Squire Road, Winchester, MA 01890
1 / 42
Active
Price
Open

$2,399,000

54 Squire Road, Winchester, MA 01890

4 bds
|
4.5 ba
|
4450 sqft
MLS® 73555666Single Family Residence
The Marino Group Collection - Anthony Marino
Property at 1 Plymouth Rd., Winchester, MA 01890
1 / 28
Active
New
Open

$3,299,000

1 Plymouth Rd., Winchester, MA 01890

7 bds
|
7.5 ba
|
7226 sqft
MLS® 73585058Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 4 Churchill Road, Winchester, MA 01890
1 / 42
Active
Price
Open

$1,649,000

4 Churchill Road, Winchester, MA 01890

3 bds
|
2 ba
|
2421 sqft
MLS® 73572661Single Family Residence
Compass - Kim Covino & Co. Team
Property at 143 Arlington Street, Winchester, MA 01890
1 / 42
Active

$1,599,000

143 Arlington Street, Winchester, MA 01890

5 bds
|
2 ba
|
2944 sqft
MLS® 73575069Single Family Residence
Compass - Kim Covino & Co. Team
Property at 7 Hutchinson Road, Winchester, MA 01890
1 / 42
Active

$3,450,000

7 Hutchinson Road, Winchester, MA 01890

6 bds
|
4.5 ba
|
5735 sqft
MLS® 73561703Single Family Residence
Compass - Kim Covino & Co. Team
Property at 8 North Gateway, Winchester, MA 01890
1 / 39
Active
Open

$1,299,000

8 North Gateway, Winchester, MA 01890

6 bds
|
2.5 ba
|
3910 sqft
MLS® 73584820Single Family Residence
Compass - Kim Covino & Co. Team
Property at 53 Lake Street, Winchester, MA 01890
1 / 42
Active
Price

$1,025,000

53 Lake Street, Winchester, MA 01890

3 bds
|
2.5 ba
|
2235 sqft
MLS® 73519082Single Family Residence
Compass - Kim Covino & Co. Team
Property at 25 Arlington St, Winchester, MA 01890
1 / 32
Active
Open

$1,529,000

25 Arlington St, Winchester, MA 01890

4 bds
|
3.5 ba
|
2709 sqft
MLS® 73584817Single Family Residence
Coldwell Banker Realty - Lexington - Domingo Medina
Property at 85 High St, Winchester, MA 01890
1 / 38
Active
Price
Open

$1,899,000

85 High St, Winchester, MA 01890

4 bds
|
2.5 ba
|
3757 sqft
MLS® 73565817Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Catherine Albiani
Property at 247 Washington St #11, Winchester, MA 01890
1 / 23
Active
Price

$610,000

247 Washington St #11, Winchester, MA 01890

3 bds
|
2.5 ba
|
1494 sqft
MLS® 73549877Condominium
Coldwell Banker Realty - Lexington - Heejeong Joo
Property at 1 Overlook Way, Winchester, MA 01890
1 / 40
Active
Open

$1,850,000

1 Overlook Way, Winchester, MA 01890

4 bds
|
2.5 ba
|
3092 sqft
MLS® 73581571Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Lynne Russo
Property at 465 Washington Street, Winchester, MA 01890
1 / 28
Active
Open

$1,300,000

465 Washington Street, Winchester, MA 01890

4 bds
|
2.5 ba
|
2666 sqft
MLS® 73574928Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 14 Nassau Drive, Winchester, MA 01890
1 / 30
Active
Price
Open

$2,799,000

14 Nassau Drive, Winchester, MA 01890

6 bds
|
6 ba
|
6968 sqft
MLS® 73500890Single Family Residence
WINN Real Estate & Consulting - Weidong Li
Property at 23 Stone Ave., Winchester, MA 01890
1 / 35
Active Under Contract

$1,000,000

23 Stone Ave., Winchester, MA 01890

3 bds
|
1 ba
|
1908 sqft
MLS® 73581744Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Dara Singleton
Property at 8 Priscilla Lane, Winchester, MA 01890
1 / 35
Active Under Contract

$2,995,000

8 Priscilla Lane, Winchester, MA 01890

5 bds
|
5.5 ba
|
6500 sqft
MLS® 73574330Single Family Residence
Rise Signature Homes - The Pezzano Group
Page 1 of 3

Brokerage Information

Gundersheim Group Real Estate

10 Lincoln St, Newton, MA, 02461

(617) 997-8272

Market Area Served

Boston, Somerville, Newton, Brookline, Wellesley, Needham and many more.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Melanie Gundersheim

Buy or sell in Boston, Newton, Needham, Brookline, Wellesley, and Somerville with clear guidance, local insight, and a calm, strategic process.

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Homes for sale in Winchester, MA: market at a glance

As of October 3, 2026, there are 66 homes for sale in Winchester, MA, with a median list price of $1,312,500. In July 2026, the median sale price for homes in Winchester, MA was $1,775,000, up 38.7% from a year earlier.

Homes for sale
66
Median list price
$1,312,500
Median sale price (July 2026)
$1,775,000
Median days on market (July 2026)
22 days
  • Winchester market report
  • Winchester single-family homes for sale
  • Winchester condos for sale
  • Winchester multi-family homes for sale

Homes for sale near Winchester

  • Woburn, MA
  • West Medford, MA
  • Arlington Heights, MA
  • Medford, MA
  • Stoneham, MA
  • Arlington, MA
  • Lexington, MA
  • Melrose, MA

Common questions about Winchester, MA real estate

How many homes are for sale in Winchester, MA?

As of October 3, 2026, there are 66 homes for sale in Winchester, MA, including 45 single-family homes, 19 condos and 1 multi-family home.

What is the median home price in Winchester, MA?

The median list price of homes for sale in Winchester, MA is $1,312,500. Homes that sold in July 2026 had a median sale price of $1,775,000, up 38.7% from a year earlier.

How long do homes take to sell in Winchester, MA?

Homes in Winchester, MA that sold in July 2026 had a median of 22 days on market. Homes currently for sale show a median of about 23 days on market.

What types of homes are for sale in Winchester, MA?

The homes for sale in Winchester, MA include 45 single-family homes, 19 condos and 1 multi-family home.