View 50 Brooks Street Winchester, MA MLS# 73510897
  • Recently Listed
1 of 42
$2,595,000
4

Beds

3.1

Baths

4,403

Sq.Ft.

50 Brooks Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 6 Ivy Circle Winchester, MA MLS# 73510713
  • Recently Listed
1 of 36
$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
View 15 Yale St Winchester, MA MLS# 73510619
  • Recently Listed
1 of 39
$2,750,000
7

Beds

3.1

Baths

3,676

Sq.Ft.

15 Yale St

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
The time to sell is now! THE TIME TO SELL IS NOW!
View 15 York Road Winchester, MA MLS# 73510389
  • Recently Listed
1 of 38
$2,500,000
5

Beds

3.1

Baths

4,500

Sq.Ft.

15 York Road

Winchester, MA

Listed By: Nannette Shanahan Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 2 George Road # 2 Winchester, MA MLS# 73510206
  • Recently Listed
1 of 26
$649,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

2 George Road # 2

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 6 Hancock St Winchester, MA MLS# 73510153
  • Recently Listed
1 of 31
$1,250,000
5

Beds

1.1

Baths

2,688

Sq.Ft.

6 Hancock St

Winchester, MA

Listed By: Pirani & Wile Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 7 Cliff Street Winchester, MA MLS# 73509698
  • Recently Listed with Virtual Tour
1 of 42
$2,490,000
6

Beds

3.1

Baths

4,573

Sq.Ft.

7 Cliff Street

Winchester, MA

Listed By: Elizabeth Darby Courtesy of BERKSHIRE HATHAWAY HOMESERVICES COMMONWEALTH REAL ESTATE
View 9 Governors Avenue # 2 Winchester, MA MLS# 73509305
  • Recently Listed with Virtual Tour
1 of 37
$899,000
3

Beds

1.1

Baths

1,799

Sq.Ft.

9 Governors Avenue # 2

Winchester, MA

Listed By: Vita Realty Group Courtesy of COMPASS
View 12 Hancock St Winchester, MA MLS# 73508959
  • Recently Listed
1 of 39
$1,299,000
3

Beds

1.1

Baths

2,030

Sq.Ft.

12 Hancock St

Winchester, MA

Listed By: Elena Langlois Courtesy of COMPASS
View 307 Cross Street Winchester, MA MLS# 73508927
  • Recently Listed with Virtual Tour
1 of 42
$1,700,000
5

Beds

5.0

Baths

3,500

Sq.Ft.

307 Cross Street

Winchester, MA

Listed By: Dara Singleton Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 10 Graystone Cir # 10 Winchester, MA MLS# 73508184
  • Recently Listed
1 of 32
$1,800,000
2

Beds

3.1

Baths

3,874

Sq.Ft.

10 Graystone Cir # 10

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 10 Graystone Cir # 10 Winchester, MA MLS# 73508182
  • Recently Listed
1 of 32
$1,800,000
2

Beds

3.1

Baths

3,874

Sq.Ft.

10 Graystone Cir # 10

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 955 Main St # 305 Winchester, MA MLS# 73507899
  • Recently Listed
1 of 33
$1,150,000
2,054

Sq.Ft.

955 Main St # 305

Winchester, MA

Listed By: Zuby Singh Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 71 Sargent Road Winchester, MA MLS# 73501230
  • Recently Listed with Virtual Tour
1 of 42
$1,399,000
3

Beds

3.1

Baths

2,936

Sq.Ft.

71 Sargent Road

Winchester, MA

Listed By: Bob Bittelari Courtesy of BERKSHIRE HATHAWAY HOMESERVICES COMMONWEALTH REAL ESTATE
View 16 Glenwood Ave Winchester, MA MLS# 73507145
  • Recently Listed
1 of 41
$2,200,000
6

Beds

4.1

Baths

6,900

Sq.Ft.

16 Glenwood Ave

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 16 Glenwood Ave Winchester, MA MLS# 73507137
  • Recently Listed
1 of 41
$2,200,000
6

Beds

4.1

Baths

6,900

Sq.Ft.

16 Glenwood Ave

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 7 Conant Road # 53 Winchester, MA MLS# 73507003
$725,000
2

Beds

2.0

Baths

1,588

Sq.Ft.

7 Conant Road # 53

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 21 Bellevue Avenue Winchester, MA MLS# 73506730
  • Recently Listed with Virtual Tour
1 of 42
$2,699,000
5

Beds

4.0

Baths

5,950

Sq.Ft.

21 Bellevue Avenue

Winchester, MA

Listed By: Giordana Fioravanti Smith Courtesy of BERKSHIRE HATHAWAY HOMESERVICES COMMONWEALTH REAL ESTATE
View 6 Oakland Circle Winchester, MA MLS# 73505351
  • Virtual Tour
1 of 40
$1,549,000
4

Beds

2.1

Baths

3,298

Sq.Ft.

6 Oakland Circle

Winchester, MA

Listed By: Seeme Moreira Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 205 Washington St. Winchester, MA MLS# 73503540
$1,349,000
3

Beds

2.0

Baths

2,355

Sq.Ft.

205 Washington St.

Winchester, MA

Listed By: Jayne Zeamer Courtesy of COLDWELL BANKER REALTY - BOSTON

About Winchester

Listings in Winchester, MA

49

Estimated median home price

$1,800,000
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 1
$300K - 400K 4
$400K - 500K 0
$500K - 600K 0
$600K - 700K 1
$700K - 800K 2
$800K - 900K 1
$900K - 1M 1
$1M - Max 39

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 34
Townhouse 0
Condo 12
Commercial 2
Rental 21
Lots and Land 0
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 4/30/2026)

Information deemed reliable but not guaranteed.

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

Data is updated as of 5/1/2026.

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.