Winchester Massachusetts Homes for Sale

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View 25 Canterbury Road Winchester, MA MLS# 73600361
  • Recently Listed with Virtual Tour
1 of 42
$3,499,000
6

Beds

5.1

Baths

6,327

Sq.Ft.

25 Canterbury Road

Winchester, MA

Listed By: Vita Realty Group Courtesy of COMPASS
View 9 Watson Pl Winchester, MA MLS# 73599800
  • Recently Listed
1 of 10
$1,599,000
3

Beds

2.1

Baths

1,920

Sq.Ft.

9 Watson Pl

Winchester, MA

Listed By: Pirani & Wile Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 15 Madison Ave W Winchester, MA MLS# 73599772
  • Recently Listed with Virtual Tour
1 of 42
$1,449,000
4

Beds

2.1

Baths

2,855

Sq.Ft.

15 Madison Ave W

Winchester, MA

Listed By: Andersen Group Realty Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST
The time to sell is now! THE TIME TO SELL IS NOW!
View 419 Washington Street # 419 Winchester, MA MLS# 73599604
$675,000
3

Beds

1.0

Baths

1,524

Sq.Ft.

419 Washington Street # 419

Winchester, MA

Listed By: The Marrocco Group Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 421 Washington Street # 421 Winchester, MA MLS# 73599605
$649,000
3

Beds

1.0

Baths

1,422

Sq.Ft.

421 Washington Street # 421

Winchester, MA

Listed By: The Marrocco Group Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 85 High Street Winchester, MA MLS# 73596915
  • Recently Listed
1 of 36
$1,749,000
4

Beds

2.1

Baths

3,757

Sq.Ft.

85 High Street

Winchester, MA

Listed By: Catherine Albiani Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 67-69 Hemingway St Winchester, MA MLS# 73595844
  • Recently Listed
1 of 6
$1,450,000
0.0

Baths

67-69 Hemingway St

Winchester, MA

Listed By: Pirani & Wile Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 28 Olive St Winchester, MA MLS# 73595417
  • Recently Listed
1 of 41
$1,049,900
3

Beds

2.0

Baths

1,783

Sq.Ft.

28 Olive St

Winchester, MA

Listed By: Ethan Forrest Courtesy of THE ALAND REALTY GROUP LLC
View 67-69 Hemingway St Winchester, MA MLS# 73594547
  • Recently Listed
1 of 6
$1,450,000
8

Beds

4.2

Baths

6,200

Sq.Ft.

67-69 Hemingway St

Winchester, MA

Listed By: Pirani & Wile Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 5 Forest Cir Winchester, MA MLS# 73594545
  • Recently Listed
1 of 10
$2,999,000
5

Beds

4.1

Baths

4,900

Sq.Ft.

5 Forest Cir

Winchester, MA

Listed By: Pirani & Wile Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 18 Middlesex St Winchester, MA MLS# 73593868
$2,650,000
4

Beds

4.1

Baths

5,233

Sq.Ft.

18 Middlesex St

Winchester, MA

Listed By: Jennifer Taves Courtesy of COLDWELL BANKER REALTY - BOSTON
View 15 Foxcroft Rd Winchester, MA MLS# 73593484
$3,799,000
8

Beds

4.2

Baths

7,081

Sq.Ft.

15 Foxcroft Rd

Winchester, MA

Listed By: Karen S. Garrett Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 419-421 Washington St Winchester, MA MLS# 73592723
$1,249,000
6

Beds

2.0

Baths

2,946

Sq.Ft.

419-421 Washington St

Winchester, MA

Listed By: The Marrocco Group Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 18 Surrey Road Winchester, MA MLS# 73592433
$2,950,000
6

Beds

4.0

Baths

4,752

Sq.Ft.

18 Surrey Road

Winchester, MA

Listed By: Mary Kelly Courtesy of CENTURY 21 PROPERTY CENTRAL INC.
View 80 Nelson St Winchester, MA MLS# 73591108
$815,000
2

Beds

1.0

Baths

1,489

Sq.Ft.

80 Nelson St

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 14 Nassau Drive Winchester, MA MLS# 73500890
$2,750,000
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 6 Aricia Ln Winchester, MA MLS# 73590311
$1,399,000
3

Beds

2.1

Baths

1,975

Sq.Ft.

6 Aricia Ln

Winchester, MA

Listed By: Pirani & Wile Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 21 Amberwood Dr Winchester, MA MLS# 73588059
  • Virtual Tour
1 of 42
$1,999,000
5

Beds

3.1

Baths

4,063

Sq.Ft.

21 Amberwood Dr

Winchester, MA

Listed By: Gayle Winters & Co. Team Courtesy of COMPASS
View 39 Henry Street Winchester, MA MLS# 73585414
  • Virtual Tour
1 of 22
$850,000
3

Beds

1.0

Baths

1,313

Sq.Ft.

39 Henry Street

Winchester, MA

Listed By: Kelly Batti Courtesy of COLDWELL BANKER REALTY - BELMONT
View 15 Vinson Circle Winchester, MA MLS# 73585235
$18,000,000
6

Beds

6.1

Baths

10,000

Sq.Ft.

15 Vinson Circle

Winchester, MA

Listed By: Anthony Marino Courtesy of THE MARINO GROUP COLLECTION

About Winchester

Listings in Winchester, MA

61

Estimated median home price

$1,450,000
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 4
$700K - 800K 2
$800K - 900K 3
$900K - 1M 4
$1M - Max 44

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 42
Townhouse 0
Condo 11
Commercial 4
Rental 33
Lots and Land 1
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 11/13/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 11/13/2026.

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