View 112 Highland Avenue Winchester, MA MLS# 73515135
  • Recently Listed
1 of 42
$2,495,000
6

Beds

3.1

Baths

5,121

Sq.Ft.

112 Highland Avenue

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 16 Glenwood Ave Winchester, MA MLS# 73507137
  • Virtual Tour
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# 73507145
  • Virtual Tour
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 276 High Street Winchester, MA MLS# 73496396
  • Virtual Tour
1 of 38
$2,195,000
5

Beds

3.1

Baths

5,006

Sq.Ft.

276 High 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 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 12 Cox Rd Winchester, MA MLS# 73511596
  • Recently Listed
1 of 41
$1,699,000
4

Beds

2.1

Baths

2,818

Sq.Ft.

12 Cox Rd

Winchester, MA

Listed By: Darryl E. Brian Courtesy of RE/MAX BENTLEY'S
View 41 Sunset Road Winchester, MA MLS# 73520906
  • Recently Listed with Virtual Tour
1 of 42
$1,689,000
3

Beds

2.0

Baths

3,090

Sq.Ft.

41 Sunset Road

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 7 Sherman Place # 7 Winchester, MA MLS# 73514887
  • Recently Listed with Virtual Tour
1 of 40
$1,495,000
4

Beds

2.1

Baths

2,605

Sq.Ft.

7 Sherman Place # 7

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 7 Sherman Place # 7 Winchester, MA MLS# 73514945
  • Recently Listed with Virtual Tour
1 of 40
$1,495,000
4

Beds

2.1

Baths

2,605

Sq.Ft.

7 Sherman Place # 7

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 465 Washington St # 465 Winchester, MA MLS# 73516536
  • Recently Listed
1 of 26
$1,300,000
4

Beds

2.1

Baths

2,666

Sq.Ft.

465 Washington St # 465

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 465 Washington St Winchester, MA MLS# 73516539
  • Recently Listed
1 of 26
$1,300,000
4

Beds

2.1

Baths

2,666

Sq.Ft.

465 Washington St

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 6 Alden Lane Winchester, MA MLS# 73520993
  • Recently Listed
1 of 24
$1,300,000
3

Beds

2.0

Baths

1,511

Sq.Ft.

6 Alden Lane

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 129 Washington St # 129 Winchester, MA MLS# 73513572
  • Recently Listed with Virtual Tour
1 of 31
$1,299,000
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 6 Hancock St Winchester, MA MLS# 73510153
$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 53 Lake Street Winchester, MA MLS# 73519082
  • Recently Listed
1 of 36
$1,225,000
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
View 63-65 Harvard Street Winchester, MA MLS# 73515601
  • Recently Listed
1 of 33
$1,150,000
5

Beds

3.0

Baths

2,186

Sq.Ft.

63-65 Harvard Street

Winchester, MA

Listed By: Beth Sager Group Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST
View 83 Church Street # 15 Winchester, MA MLS# 73497739
  • Virtual Tour
1 of 34
$1,100,000
2

Beds

1.1

Baths

1,365

Sq.Ft.

83 Church Street # 15

Winchester, MA

Listed By: Paula R. Sughrue Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 41 Cross St Winchester, MA MLS# 73520534
  • Recently Listed with Virtual Tour
1 of 42
$999,000
4

Beds

2.0

Baths

2,085

Sq.Ft.

41 Cross St

Winchester, MA

Listed By: Andersen Group Realty Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST

About Winchester

Listings in Winchester, MA

54

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 1
$300K - 400K 5
$400K - 500K 0
$500K - 600K 0
$600K - 700K 2
$700K - 800K 2
$800K - 900K 0
$900K - 1M 2
$1M - Max 42

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 36
Townhouse 0
Condo 14
Commercial 2
Rental 31
Lots and Land 0
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 5/20/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 5/21/2026.

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