49 total properties
View 65 High Street Winchester, MA MLS# 73498871
$1,399,800
6

Beds

3.0

Baths

2,658

Sq.Ft.

65 High Street

Winchester, MA

Listed By: Anna Jung Courtesy of K STADIUM REALTY INC
View 34 Robinhood Road Winchester, MA MLS# 73486878
$1,524,000
4

Beds

2.1

Baths

3,380

Sq.Ft.

34 Robinhood Road

Winchester, MA

Listed By: Janet Halloran Courtesy of RE/MAX REAL ESTATE CENTER
View 29 Pilgrim Dr Winchester, MA MLS# 73491480
  • Virtual Tour
1 of 42
$1,749,000
5

Beds

3.0

Baths

3,271

Sq.Ft.

29 Pilgrim Dr

Winchester, MA

Listed By: Anne Spry Courtesy of BARRETT SOTHEBY'S INTERNATIONAL REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 1 Town Way Winchester, MA MLS# 73466233
  • Virtual Tour
1 of 40
$1,874,000
3

Beds

3.1

Baths

3,010

Sq.Ft.

1 Town Way

Winchester, MA

Listed By: Vita Realty Group Courtesy of COMPASS
View 2 Gershon Way # 2 Winchester, MA MLS# 73496895
  • Virtual Tour
1 of 33
$1,899,000
3

Beds

2.1

Baths

2,306

Sq.Ft.

2 Gershon Way # 2

Winchester, MA

Listed By: The Marrocco Group Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 2 Gershon Way Winchester, MA MLS# 73496897
  • Virtual Tour
1 of 34
$1,899,000
3

Beds

2.1

Baths

2,306

Sq.Ft.

2 Gershon Way

Winchester, MA

Listed By: The Marrocco Group Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 94 Johnson Road Winchester, MA MLS# 73497889
  • Recently Listed with Virtual Tour
1 of 37
$1,899,999
4

Beds

3.0

Baths

3,512

Sq.Ft.

94 Johnson Road

Winchester, MA

Listed By: Vita Realty Group Courtesy of COMPASS
View 237 Swanton Street Winchester, MA MLS# 73496811
  • Recently Listed with Virtual Tour
1 of 34
$1,995,000
5

Beds

4.0

Baths

4,334

Sq.Ft.

237 Swanton Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 15 Cabot St Winchester, MA MLS# 73502658
  • Recently Listed
1 of 34
$2,149,000
4

Beds

2.1

Baths

3,123

Sq.Ft.

15 Cabot St

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 276 High Street Winchester, MA MLS# 73496396
  • Recently Listed with Virtual Tour
1 of 38
$2,299,000
5

Beds

3.1

Baths

5,006

Sq.Ft.

276 High Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 15 Gershon Way # 15 Winchester, MA MLS# 73495315
$2,395,000
3

Beds

3.1

Baths

4,087

Sq.Ft.

15 Gershon Way # 15

Winchester, MA

Listed By: Moira Lown Courtesy of COLDWELL BANKER REALTY - WELLESLEY
View 15 Gershon Way # 15 Winchester, MA MLS# 73495350
$2,395,000
3

Beds

3.1

Baths

4,087

Sq.Ft.

15 Gershon Way # 15

Winchester, MA

Listed By: Moira Lown Courtesy of COLDWELL BANKER REALTY - WELLESLEY
View 53 Winford Way Winchester, MA MLS# 73481323
  • Virtual Tour
1 of 16
$2,799,000
5

Beds

4.0

Baths

5,083

Sq.Ft.

53 Winford Way

Winchester, MA

Listed By: Andersen Group Realty Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST
View 2 Edgewater Place Winchester, MA MLS# 73498843
  • Recently Listed
1 of 32
$2,800,000
4

Beds

4.1

Baths

3,945

Sq.Ft.

2 Edgewater Place

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 14 Nassau Drive Winchester, MA MLS# 73500890
  • Recently Listed
1 of 36
$2,850,000
6

Beds

5.2

Baths

6,968

Sq.Ft.

14 Nassau Drive

Winchester, MA

Listed By: Weidong Li Courtesy of WINN REAL ESTATE & CONSULTING
View 10 Dartmouth Street Winchester, MA MLS# 73496399
  • Recently Listed
1 of 42
$2,999,000
5

Beds

2.2

Baths

4,028

Sq.Ft.

10 Dartmouth Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 12 Salisbury Street Winchester, MA MLS# 73496654
  • Virtual Tour
1 of 42
$3,200,000
6

Beds

4.1

Baths

5,107

Sq.Ft.

12 Salisbury Street

Winchester, MA

Listed By: Karen S. Garrett Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 257 High Street Winchester, MA MLS# 73499287
  • Virtual Tour
1 of 40
$3,250,000
5

Beds

5.2

Baths

7,101

Sq.Ft.

257 High Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 27 Everett Ave Winchester, MA MLS# 73468691
$3,290,000
6

Beds

5.1

Baths

7,431

Sq.Ft.

27 Everett Ave

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 74 Wedgemere Avenue Winchester, MA MLS# 73499151
  • Recently Listed
1 of 42
$3,299,000
5

Beds

4.1

Baths

5,202

Sq.Ft.

74 Wedgemere Avenue

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS

Information deemed reliable but not guaranteed.

Content © 2026 MLS Property Information Network, Inc. All Rights Reserved.

Data is updated as of 4/20/2026.

The real estate information and related content displayed on this site is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

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 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 or leasing 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 or leasing. 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.