View 22 Hollywood Rd Winchester, MA MLS# 73527768
  • Recently Listed with Virtual Tour
1 of 39
$1,999,000
5

Beds

2.2

Baths

3,136

Sq.Ft.

22 Hollywood Rd

Winchester, MA

Listed By: Andersen Group Realty Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST
View 7-9 Ridge St Winchester, MA MLS# 73527738
  • Recently Listed with Virtual Tour
1 of 39
$1,550,000
5

Beds

3.2

Baths

3,360

Sq.Ft.

7-9 Ridge St

Winchester, MA

Listed By: The Synergy Group Courtesy of THE SYNERGY GROUP
View 41 Cross St Winchester, MA MLS# 73527486
  • 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 18 Grayson Rd Winchester, MA MLS# 73526595
  • Recently Listed with Virtual Tour
1 of 37
$1,699,000
3

Beds

2.1

Baths

2,992

Sq.Ft.

18 Grayson Rd

Winchester, MA

Listed By: Andersen Group Realty Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST
View 78 Bacon Street Winchester, MA MLS# 73526460
  • Recently Listed
1 of 42
$2,599,000
5

Beds

3.1

Baths

5,230

Sq.Ft.

78 Bacon Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 303 Washington Street Winchester, MA MLS# 73526417
  • Recently Listed
1 of 42
$1,375,000
6

Beds

2.0

Baths

5,047

Sq.Ft.

303 Washington Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 30 Rangeley Road Winchester, MA MLS# 73526416
  • Recently Listed
1 of 42
$2,200,000
5

Beds

3.1

Baths

4,744

Sq.Ft.

30 Rangeley Road

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 94 Johnson Road Winchester, MA MLS# 73525571
  • Recently Listed with Virtual Tour
1 of 40
$1,799,000
4

Beds

3.0

Baths

3,366

Sq.Ft.

94 Johnson Road

Winchester, MA

Listed By: Paula R. Sughrue Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 53 Winford Way Winchester, MA MLS# 73525195
  • Recently Listed with Virtual Tour
1 of 16
$2,799,000
5

Beds

4.0

Baths

5,083

Sq.Ft.

53 Winford Way

Winchester, MA

Listed By: Andersen Group Realty Courtesy of KELLER WILLIAMS REALTY BOSTON NORTHWEST
View 4 Lawrence St Winchester, MA MLS# 73524328
  • Recently Listed
1 of 40
$3,099,000
6

Beds

8.0

Baths

7,168

Sq.Ft.

4 Lawrence St

Winchester, MA

Listed By: Burbs to Boston Courtesy of COMPASS
View 200 Swanton St # 303 Winchester, MA MLS# 73524262
  • Recently Listed
1 of 19
$505,000
2

Beds

1.0

Baths

822

Sq.Ft.

200 Swanton St # 303

Winchester, MA

Listed By: Joan Powell Courtesy of REMAX ANDREW REALTY SERVICES
View 105 Thornberry Rd Winchester, MA MLS# 73523785
  • Recently Listed with Virtual Tour
1 of 35
$1,899,000
5

Beds

2.1

Baths

3,278

Sq.Ft.

105 Thornberry Rd

Winchester, MA

Listed By: The Marrocco Group Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 8 Hawthorne Winchester, MA MLS# 73522773
  • Recently Listed
1 of 24
$1,925,000
5

Beds

2.2

Baths

3,315

Sq.Ft.

8 Hawthorne

Winchester, MA

Listed By: H. Elaine Song Courtesy of COLDWELL BANKER REALTY - LEXINGTON
View 22 Arthur St # 22 Winchester, MA MLS# 73522504
  • Recently Listed
1 of 13
$414,500
2

Beds

1.0

Baths

1,121

Sq.Ft.

22 Arthur St # 22

Winchester, MA

Listed By: Karen Morand Courtesy of MCO REALTY SERVICE, LLC
View 2 Eaton Ct Winchester, MA MLS# 73522338
  • Virtual Tour
1 of 36
$1,250,000
3

Beds

2.0

Baths

2,192

Sq.Ft.

2 Eaton Ct

Winchester, MA

Listed By: Robert Ellington Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
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 41 Sunset Road Winchester, MA MLS# 73520906
  • 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 2 Atherton Rd Winchester, MA MLS# 73519229
  • Recently Listed
1 of 38
$3,600,000
6

Beds

6.1

Baths

7,400

Sq.Ft.

2 Atherton Rd

Winchester, MA

Listed By: Brooke Zarbano Courtesy of REGATTA 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 18 Middlesex St Winchester, MA MLS# 73518621
  • Recently Listed
1 of 32
$2,795,000
4

Beds

4.1

Baths

5,233

Sq.Ft.

18 Middlesex St

Winchester, MA

Listed By: Tina Natale Courtesy of LUXURY LIVING REAL ESTATE

About Winchester

Listings in Winchester, MA

56

Estimated median home price

$1,749,000
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 5
$400K - 500K 1
$500K - 600K 1
$600K - 700K 1
$700K - 800K 1
$800K - 900K 0
$900K - 1M 2
$1M - Max 45

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 39
Townhouse 0
Condo 11
Commercial 2
Rental 33
Lots and Land 0
Condo/Town/CoOp 0
CoOp 0
Multi Family 4
Mobile Home 0
Farms 0

(Data as of 6/2/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 6/2/2026.

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