View 114 Johnson Rd Winchester, MA MLS# 73478721
  • Recently Listed with Virtual Tour
1 of 42
$1,795,000
3

Beds

3.0

Baths

3,182

Sq.Ft.

114 Johnson Rd

Winchester, MA

Listed By: Rosemary Kelleher Courtesy of LAER REALTY PARTNERS
View 149 Horn Pond Brook Road Winchester, MA MLS# 73478668
  • Recently Listed with Virtual Tour
1 of 33
$1,289,900
5

Beds

2.0

Baths

2,331

Sq.Ft.

149 Horn Pond Brook Road

Winchester, MA

Listed By: Nancy Ciampa McLaughlin Courtesy of REDFIN CORP.
View 9 Charles Road # 9 Winchester, MA MLS# 73478441
  • Recently Listed
1 of 33
$599,000
3

Beds

1.1

Baths

973

Sq.Ft.

9 Charles Road # 9

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
The time to sell is now! THE TIME TO SELL IS NOW!
View 76 Woodside Road Winchester, MA MLS# 73476558
$999,000
4

Beds

2.0

Baths

1,552

Sq.Ft.

76 Woodside Road

Winchester, MA

Listed By: Michael Pierce Courtesy of MYSTIC PROPERTIES REAL ESTATE
View 320 Washington St Winchester, MA MLS# 73476114
$1,000,000
3

Beds

1.1

Baths

1,749

Sq.Ft.

320 Washington St

Winchester, MA

Listed By: John D. Conroy Courtesy of EAST COAST REALTY, INC.
View 2 Canterbury Rd Winchester, MA MLS# 73475677
  • Virtual Tour
1 of 33
$1,399,000
3

Beds

2.1

Baths

2,370

Sq.Ft.

2 Canterbury Rd

Winchester, MA

Listed By: Paula R. Sughrue Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 37 Mayflower Road Winchester, MA MLS# 73475646
  • Recently Listed
1 of 42
$3,537,000
7

Beds

7.1

Baths

8,540

Sq.Ft.

37 Mayflower Road

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 8-10 Russell Road Winchester, MA MLS# 73475004
  • Recently Listed
1 of 39
$995,000
4

Beds

2.0

Baths

1,800

Sq.Ft.

8-10 Russell Road

Winchester, MA

Listed By: Rajive Dogra Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 54 Johnson Rd Winchester, MA MLS# 73474290
  • Recently Listed with Virtual Tour
1 of 42
$3,499,000
5

Beds

7.1

Baths

6,899

Sq.Ft.

54 Johnson Rd

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 15 Mayflower Rd Winchester, MA MLS# 73474189
  • Recently Listed
1 of 39
$3,425,000
7

Beds

7.1

Baths

7,226

Sq.Ft.

15 Mayflower Rd

Winchester, MA

Listed By: The Sarkis Team Courtesy of DOUGLAS ELLIMAN REAL ESTATE - THE SARKIS TEAM
View 6 Marchant Road Winchester, MA MLS# 73473803
  • Recently Listed with Virtual Tour
1 of 42
$1,350,000
3

Beds

2.1

Baths

2,153

Sq.Ft.

6 Marchant Road

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 5 Squire Rd Winchester, MA MLS# 73471882
  • Virtual Tour
1 of 42
$1,899,000
6

Beds

3.1

Baths

4,696

Sq.Ft.

5 Squire Rd

Winchester, MA

Listed By: Andersen Group Realty Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST
View 25 Myopia Road Winchester, MA MLS# 73471735
  • Virtual Tour
1 of 31
$3,390,000
4

Beds

3.1

Baths

4,847

Sq.Ft.

25 Myopia Road

Winchester, MA

Listed By: Wenjun Cao Courtesy of ENGEL & VOLKERS BOSTON
View 63 Shore Road # 14 Winchester, MA MLS# 73471078
$400,000
1.0

Baths

621

Sq.Ft.

63 Shore Road # 14

Winchester, MA

Listed By: Aldo Masciave Courtesy of LEADING EDGE REAL ESTATE
View 61 Grove Street Winchester, MA MLS# 73470986
  • Virtual Tour
1 of 42
$2,199,000
5

Beds

4.1

Baths

4,798

Sq.Ft.

61 Grove Street

Winchester, MA

Listed By: Dorothea Feffer Courtesy of CHURCHILL PROPERTIES
View 27 Everett Ave Winchester, MA MLS# 73468691
$3,599,000
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 10 Viking Rd Winchester, MA MLS# 73467030
  • Virtual Tour
1 of 42
$2,595,000
4

Beds

4.0

Baths

5,674

Sq.Ft.

10 Viking Rd

Winchester, MA

Listed By: Anne Spry Courtesy of BARRETT SOTHEBY'S INTERNATIONAL REALTY
View 1 Town Way Winchester, MA MLS# 73466233
  • Virtual Tour
1 of 40
$1,899,000
3

Beds

3.1

Baths

3,010

Sq.Ft.

1 Town Way

Winchester, MA

Listed By: Vita Realty Group Courtesy of COMPASS
View 263 Highland Ave Winchester, MA MLS# 73461480
  • Virtual Tour
1 of 42
$1,649,000
4

Beds

2.2

Baths

3,343

Sq.Ft.

263 Highland Ave

Winchester, MA

Listed By: Seeme Moreira Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 237 Swanton Street Winchester, MA MLS# 73459838
  • Virtual Tour
1 of 35
$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

About Winchester

Listings in Winchester, MA

25

Estimated median home price

$1,899,000
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 3
$400K - 500K 0
$500K - 600K 1
$600K - 700K 0
$700K - 800K 0
$800K - 900K 0
$900K - 1M 3
$1M - Max 18

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 20
Townhouse 0
Condo 3
Commercial 1
Rental 18
Lots and Land 0
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 2/20/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 2/20/2026.

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