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60+ Homes for Sale in Winchester, MA

67 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 63 Wedgemere Avenue, Winchester, MA 01890
1 / 39
Active
New
Open

$2,399,000

63 Wedgemere Avenue, Winchester, MA 01890

4 bds
|
3 ba
|
3550 sqft
MLS® 73587441Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Paula R. Sughrue
Property at 7 Wainwright Rd. ##47, Winchester, MA 01890
1 / 37
Active Under Contract

$1,295,000

7 Wainwright Rd. ##47, Winchester, MA 01890

3 bds
|
3 ba
|
2145 sqft
MLS® 73580454Condominium
Better Homes and Gardens Real Estate - The Shanahan Group - Felicity F. Tuttle
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 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

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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 26 Mayflower Road, Winchester, MA 01890
1 / 42
Active Under Contract

$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 79 Grove St, Winchester, MA 01890
1 / 42
Active Under Contract
Price

$1,870,000

79 Grove St, Winchester, MA 01890

5 bds
|
3.5 ba
|
3210 sqft
MLS® 73545952Single Family Residence
Gibson Sotheby's International Realty - Pirani & Wile Group
Property at 1 Overlook Way, Winchester, MA 01890
1 / 41
Active

$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 4 Dartmouth, Winchester, MA 01890
1 / 38
Active

$4,299,000

4 Dartmouth, Winchester, MA 01890

5 bds
|
5.5 ba
|
6526 sqft
MLS® 73574948Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 117 Highland, Winchester, MA 01890
1 / 42
Active

$1,650,000

117 Highland, Winchester, MA 01890

5 bds
|
3.5 ba
|
3722 sqft
MLS® 73573887Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Dara Singleton
Property at 666 Main St #310, Winchester, MA 01890
1 / 41
Active

$769,000

666 Main St #310, Winchester, MA 01890

2 bds
|
2 ba
|
1170 sqft
MLS® 73575558Condominium
RE/MAX Bentley's - Darryl E. Brian
Property at 200 Swanton St #717, Winchester, MA 01890
1 / 30
Active
Price

$349,900

200 Swanton St #717, Winchester, MA 01890

1 bds
|
1 ba
|
613 sqft
MLS® 73500952Condominium
Coldwell Banker Realty - Lexington - Cameron Moniz
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 4 Stone Ave, Winchester, MA 01890
1 / 38
Active

$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 39 Henry Street, Winchester, MA 01890
1 / 23
Active

$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 54 Squire Road, Winchester, MA 01890
1 / 42
Active
Price

$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 15 Vinson Circle, Winchester, MA 01890
1 / 42
Active

$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 1 Plymouth Rd., Winchester, MA 01890
1 / 28
Active

$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 60 Lake St #E, Winchester, MA 01890
1 / 20
Active
Price

$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 7 Lakeview Terrace, Winchester, MA 01890
1 / 42
Active

$2,600,000

7 Lakeview Terrace, Winchester, MA 01890

6 bds
|
3 ba
|
3534 sqft
MLS® 73578443Single Family Residence
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 25 Arlington St, Winchester, MA 01890
1 / 32
Active

$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 4 Churchill Road, Winchester, MA 01890
1 / 42
Active
Price

$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 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 8 North Gateway, Winchester, MA 01890
1 / 39
Active

$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 85 High St, Winchester, MA 01890
1 / 38
Active
Price

$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 14 Nassau Drive, Winchester, MA 01890
1 / 30
Active
Price

$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 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
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
Page 1 of 3

Brokerage Information

Commonwealth Standard Realty

10 Lincoln Street, Newton, MA 02461, USA

(617) 645-4086

Market Area Served

Newton, Brookline, Belmont, Lexington, Wellesley, Medfield, Needham, Natick, Westwood, Dedham, Boston, Wayland, Watertown 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.

Gundersheim Group Real Estate

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

As of October 7, 2026, there are 67 homes for sale in Winchester, MA, with a median list price of $1,325,000. 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
67
Median list price
$1,325,000
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 7, 2026, there are 67 homes for sale in Winchester, MA, including 46 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 $1,325,000. 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 26 days on market.

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

The homes for sale in Winchester, MA include 46 single-family homes, 19 condos and 1 multi-family home.