View 4 Dartmouth St Winchester, MA MLS# 73482952
$4,449,000
5

Beds

5.1

Baths

6,526

Sq.Ft.

4 Dartmouth St

Winchester, MA

Listed By: The Pallotta Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
View 29 Ginn Rd Winchester, MA MLS# 73534577
  • Recently Listed
1 of 39
$3,799,000
6

Beds

7.1

Baths

6,000

Sq.Ft.

29 Ginn Rd

Winchester, MA

Listed By: The Boston ONE Team Courtesy of SERHANT
View 2 Atherton Rd Winchester, MA MLS# 73519229
$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
The time to sell is now! THE TIME TO SELL IS NOW!
View 2 Everett Ave Winchester, MA MLS# 73488991
  • Virtual Tour
1 of 41
$3,475,000
7

Beds

3.3

Baths

7,043

Sq.Ft.

2 Everett Ave

Winchester, MA

Listed By: Joan Francis Sullivan Courtesy of BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP
View 37 Mayflower Road Winchester, MA MLS# 73502853
  • Virtual Tour
1 of 40
$3,379,000
7

Beds

7.1

Baths

8,540

Sq.Ft.

37 Mayflower Road

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 1 Plymouth Rd Winchester, MA MLS# 73498293
$3,299,000
7

Beds

7.1

Baths

7,226

Sq.Ft.

1 Plymouth Rd

Winchester, MA

Listed By: The Sarkis Team Courtesy of DOUGLAS ELLIMAN REAL ESTATE - THE SARKIS TEAM
View 9 Albamont Road Winchester, MA MLS# 73482275
$3,200,000
6

Beds

5.1

Baths

6,100

Sq.Ft.

9 Albamont Road

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 10 Rangeley Road Winchester, MA MLS# 73535697
  • Recently Listed
1 of 42
$3,199,000
5

Beds

4.1

Baths

5,406

Sq.Ft.

10 Rangeley Road

Winchester, MA

Listed By: Karima Alami Courtesy of COMPASS
View 8 Priscilla Ln Winchester, MA MLS# 73513501
  • Virtual Tour
1 of 35
$3,149,000
5

Beds

5.1

Baths

6,500

Sq.Ft.

8 Priscilla Ln

Winchester, MA

Listed By: The Pezzano Group Courtesy of RISE SIGNATURE HOMES
View 14 Nassau Drive Winchester, MA MLS# 73500890
$2,799,000
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 18 Middlesex St Winchester, MA MLS# 73518621
$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
View 78 Bacon Street Winchester, MA MLS# 73526460
$2,529,000
5

Beds

3.1

Baths

5,230

Sq.Ft.

78 Bacon Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 50 Brooks Street Winchester, MA MLS# 73510897
  • Virtual Tour
1 of 42
$2,450,000
4

Beds

3.1

Baths

4,403

Sq.Ft.

50 Brooks Street

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 21 Willowdale Road Winchester, MA MLS# 73534988
  • Recently Listed
1 of 42
$2,400,000
5

Beds

3.1

Baths

4,591

Sq.Ft.

21 Willowdale Road

Winchester, MA

Listed By: Kim Covino & Co. Team Courtesy of COMPASS
View 53 Winford Way Winchester, MA MLS# 73525195
  • Virtual Tour
1 of 12
$2,399,000
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 14 Hillside Ave Winchester, MA MLS# 73541163
  • Recently Listed
1 of 40
$2,380,000
4

Beds

4.1

Baths

3,881

Sq.Ft.

14 Hillside Ave

Winchester, MA

Listed By: Rebecca Huang Courtesy of WILLIAM RAVEIS R.E. & HOME SERVICES
View 211 Forest St Winchester, MA MLS# 73532996
$2,199,000
5

Beds

3.1

Baths

3,474

Sq.Ft.

211 Forest St

Winchester, MA

Listed By: Michael Gilbert Courtesy of STUART ST JAMES, INC.
View 26 N Gateway Winchester, MA MLS# 73538052
  • Recently Listed with Virtual Tour
1 of 36
$2,199,000
4

Beds

3.1

Baths

3,210

Sq.Ft.

26 N Gateway

Winchester, MA

Listed By: Pirani & Wile Group Courtesy of GIBSON SOTHEBY'S INTERNATIONAL REALTY
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 16 & 16A Glenwood Ave Winchester, MA MLS# 73507137
  • Virtual Tour
1 of 41
$2,099,000
6

Beds

4.1

Baths

6,900

Sq.Ft.

16 & 16A Glenwood Ave

Winchester, MA

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

About Winchester

Listings in Winchester, MA

58

Estimated median home price

$1,762,000
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 3
$700K - 800K 1
$800K - 900K 0
$900K - 1M 3
$1M - Max 44

Homes for Sale by Type in Winchester, MA

Property Type Count
Single Family 41
Townhouse 0
Condo 12
Commercial 2
Rental 32
Lots and Land 0
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 0

(Data as of 6/26/2026)

Information deemed reliable but not guaranteed.

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Data is updated as of 6/26/2026.

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