View 16 & 16A Glenwood Ave Winchester, MA MLS# 73507137
  • Virtual Tour
1 of 41
$2,099,000
6

Beds

4.1

Baths

6,900

Sq.Ft.

16 & 16A Glenwood Ave

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 16 Glenwood Ave Winchester, MA MLS# 73507145
  • Virtual Tour
1 of 41
$2,099,000
6

Beds

4.1

Baths

6,900

Sq.Ft.

16 Glenwood Ave

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 6 Ivy Circle Winchester, MA MLS# 73510713
$2,000,000
6

Beds

3.2

Baths

3,403

Sq.Ft.

6 Ivy Circle

Winchester, MA

Listed By: Post Advisory Group Courtesy of ENGEL & VOLKERS BOSTON
The time to sell is now! THE TIME TO SELL IS NOW!
View 15 Fieldstone Dr Winchester, MA MLS# 73537676
  • Recently Listed with Virtual Tour
1 of 42
$1,999,900
4

Beds

3.1

Baths

3,286

Sq.Ft.

15 Fieldstone Dr

Winchester, MA

Listed By: Anne Spry Courtesy of BARRETT SOTHEBY'S INTERNATIONAL REALTY
View 2 York Road Winchester, MA MLS# 73537657
  • Recently Listed with Virtual Tour
1 of 39
$1,949,000
4

Beds

3.1

Baths

3,494

Sq.Ft.

2 York Road

Winchester, MA

Listed By: Katie Tully Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 9 Wilson St Winchester, MA MLS# 73537143
  • Recently Listed
1 of 38
$1,900,000
4

Beds

3.1

Baths

2,943

Sq.Ft.

9 Wilson St

Winchester, MA

Listed By: Elena Langlois Courtesy of COMPASS
View 9 Brookside Place Winchester, MA MLS# 73534969
  • Recently Listed with Virtual Tour
1 of 41
$1,899,000
4

Beds

2.1

Baths

3,091

Sq.Ft.

9 Brookside Place

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 8 Hawthorne Road Winchester, MA MLS# 73522773
$1,885,000
5

Beds

2.2

Baths

3,315

Sq.Ft.

8 Hawthorne Road

Winchester, MA

Listed By: H. Elaine Song Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 1 Town Way Winchester, MA MLS# 73466233
  • Virtual Tour
1 of 40
$1,799,000
3

Beds

3.1

Baths

3,010

Sq.Ft.

1 Town Way

Winchester, MA

Listed By: Vita Realty Group Courtesy of COMPASS
View 94 Johnson Road Winchester, MA MLS# 73525571
  • Virtual Tour
1 of 40
$1,799,000
4

Beds

3.0

Baths

3,366

Sq.Ft.

94 Johnson Road

Winchester, MA

Listed By: Paula R. Sughrue Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 117 Highland Ave Winchester, MA MLS# 73538393
  • Recently Listed with Virtual Tour
1 of 41
$1,725,000
5

Beds

3.1

Baths

3,722

Sq.Ft.

117 Highland Ave

Winchester, MA

Listed By: Dara Singleton Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 11 Carriage Lane Winchester, MA MLS# 73537920
  • Recently Listed
1 of 38
$1,699,000
4

Beds

3.0

Baths

2,707

Sq.Ft.

11 Carriage Lane

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 10 Farrow Street Winchester, MA MLS# 73538441
  • Recently Listed with Virtual Tour
1 of 35
$1,649,000
4

Beds

3.1

Baths

2,768

Sq.Ft.

10 Farrow Street

Winchester, MA

Listed By: Collin Bray Courtesy of CENTURY 21 CITYSIDE
View 7-9 Ridge St Winchester, MA MLS# 73527738
  • Virtual Tour
1 of 39
$1,499,000
5

Beds

3.2

Baths

3,360

Sq.Ft.

7-9 Ridge St

Winchester, MA

Listed By: The Synergy Group Courtesy of THE SYNERGY GROUP
View 14 Rangeley Rdg Winchester, MA MLS# 73538612
  • Virtual Tour
1 of 39
$1,498,000
3

Beds

2.0

Baths

2,387

Sq.Ft.

14 Rangeley Rdg

Winchester, MA

Listed By: Peter Rooney Courtesy of COMPASS
View 7 Wainwright Road # 47 Winchester, MA MLS# 73534894
  • Recently Listed
1 of 32
$1,330,000
3

Beds

3.0

Baths

2,145

Sq.Ft.

7 Wainwright Road # 47

Winchester, MA

Listed By: Felicity F. Tuttle Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 38 Robinhood Rd Winchester, MA MLS# 73537786
  • Recently Listed
1 of 32
$1,225,000
3

Beds

1.2

Baths

1,736

Sq.Ft.

38 Robinhood Rd

Winchester, MA

Listed By: Catherine Albiani Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 129 Washington St # 129 Winchester, MA MLS# 73513572
$1,199,000
3

Beds

3.1

Baths

2,420

Sq.Ft.

129 Washington St # 129

Winchester, MA

Listed By: The Mary Scimemi Team Courtesy of LEADING EDGE REAL ESTATE
View 53 Lake Street Winchester, MA MLS# 73519082
$1,199,000
3

Beds

2.1

Baths

2,235

Sq.Ft.

53 Lake Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 955 Main St # 305 Winchester, MA MLS# 73507899
$1,150,000
2,054

Sq.Ft.

955 Main St # 305

Winchester, MA

Listed By: Zuby Singh Courtesy of COLDWELL BANKER REALTY - LEXINGTON

About Winchester

Listings in Winchester, MA

56

Estimated median home price

$1,799,000
Winchester MA Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Winchester, Massachusetts real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Winchester, MA.

Homes for Sale by Price in Winchester, MA

Price Count
$0 - 100K 0
$100K - 200K 0
$200K - 300K 0
$300K - 400K 5
$400K - 500K 1
$500K - 600K 1
$600K - 700K 3
$700K - 800K 1
$800K - 900K 0
$900K - 1M 3
$1M - Max 42

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 38
Townhouse 0
Condo 12
Commercial 2
Rental 33
Lots and Land 0
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/23/2026)

Information deemed reliable but not guaranteed.

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

Data is updated as of 6/23/2026.

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.