View 15 Englewood Road Winchester, MA MLS# 73480343
  • Recently Listed with Virtual Tour
1 of 29
$1,399,900
4

Beds

3.0

Baths

1,903

Sq.Ft.

15 Englewood Road

Winchester, MA

Listed By: Dara Singleton Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 17 Cranston Rd Winchester, MA MLS# 73480220
  • Recently Listed
1 of 39
$1,560,000
4

Beds

2.1

Baths

2,578

Sq.Ft.

17 Cranston Rd

Winchester, MA

Listed By: Anne Spry Courtesy of BARRETT SOTHEBY'S INTERNATIONAL REALTY
View 259 Washington Street Winchester, MA MLS# 73480199
  • Recently Listed with Virtual Tour
1 of 42
$1,349,900
4

Beds

3.1

Baths

2,590

Sq.Ft.

259 Washington Street

Winchester, MA

Listed By: Laurie Cappuccio Courtesy of CLASSIFIED REALTY GROUP
The time to sell is now! THE TIME TO SELL IS NOW!
View 45 Bacon Street Winchester, MA MLS# 73479961
  • Recently Listed
1 of 42
$2,965,000
7

Beds

6.2

Baths

7,043

Sq.Ft.

45 Bacon Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 115 Washington Street # 2A Winchester, MA MLS# 73479959
  • Recently Listed
1 of 24
$749,000
2

Beds

1.0

Baths

1,029

Sq.Ft.

115 Washington Street # 2A

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 12 Thornberry Road Winchester, MA MLS# 73479658
  • Recently Listed
1 of 31
$1,200,000
3

Beds

2.0

Baths

2,087

Sq.Ft.

12 Thornberry Road

Winchester, MA

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

About Winchester

Listings in Winchester, MA

24

Estimated median home price

$1,847,000
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 2
$1M - Max 18

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 19
Townhouse 0
Condo 3
Commercial 1
Rental 20
Lots and Land 0
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 2/25/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 2/26/2026.

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