Current Winchester, MA Market Report

Includes
• Market Trends for Winchester
• Detailed Reports including inventory and pricing.
• Homes that have an accepted offer ( Contingent, Under Agreement / Contract )

• Homes that have sold in Winchester, MA in the past 180 Days ( 6 Months )

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134 Properties

134 Featured Properties Available

Name: Open House - 12:00PM-1:00PM
Start: 2026-10-23T12:00:00
End: 2026-10-23T13:00:00
Location: 419-421 Washington St, Winchester, MA 01890

1/16 16

Open Fri 12PM-1PM

$ 1,299,000

6 Beds2 Baths2,946 SqFt

419-421 Washington St, Winchester, MA 01890

Multi-Family

Listed by The Marrocco Group of Coldwell Banker Realty - Lexington
1/34 34

Open Sun 11:30AM-1PM

$ 890,000

2 Beds1 Bath1,489 SqFt

80 Nelson St, Winchester, MA 01890

Single Family Home

Listed by Kim Covino & Co. Team of Compass
3D

Open Sun 1PM-2:30PM

$ 1,985,000

4 Beds3.5 Baths4,241 SqFt

30 Surrey Rd, Winchester, MA 01890

Single Family Home

Listed by Anne Spry of Barrett Sotheby's International Realty
1/34 34

Open Sat 12PM-1:30PM

$ 1,399,000

3 Beds2.5 Baths1,975 SqFt

6 Aricia Ln, Winchester, MA 01890

Single Family Home

Listed by Pirani & Wile Group of Gibson Sotheby's International Realty
1/42 42

Open Sat 11:30AM-1PM

$ 2,049,000

5 Beds3.5 Baths4,063 SqFt

21 Amberwood Dr, Winchester, MA 01890

Single Family Home

Listed by Gayle Winters & Co. Team of Compass
1/41 41

Open Sat 12PM-1PM

$ 700,000

2 Beds2 Baths1,240 SqFt

666 Main Street #217, Winchester, MA 01890

Condo

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate
1/16 16

Open Sat 10AM-11AM

$ 399,000

1 Bed1 Bath613 SqFt

200 Swanton St #727, Winchester, MA 01890

Condo

Listed by Alice Zheng of Shore Real Estate LLC
1/42 42

Open Sat 1:30PM-2:30PM

$ 2,400,000

6 Beds3 Baths3,534 SqFt

7 Lakeview Terrace, Winchester, MA 01890

Single Family Home

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate
1/28 28

Open Sat 12:30PM-2PM

$ 1,250,000

4 Beds2.5 Baths2,666 SqFt

465 Washington Street, Winchester, MA 01890

Single Family Home

Listed by The Pallotta Group of Gibson Sotheby's International Realty
1/28 28

Open Sat 12:30PM-2PM

$ 1,250,000

4 Beds2.5 Baths2,666 SqFt

465 Washington Street #465, Winchester, MA 01890

Condo

Listed by The Pallotta Group of Gibson Sotheby's International Realty
3D

Open Sun 11:30AM-1PM

$ 2,199,000

4 Beds3.5 Baths3,570 SqFt

19 Hancock Street, Winchester, MA 01890

Single Family Home

Listed by Vita Realty Group of Compass
3D

Open Sat 12:30PM-1:30PM

$ 1,069,000

4 Beds2.5 Baths2,411 SqFt

24 Richardson St, Winchester, MA 01890

Single Family Home

Listed by Andersen Group Realty of Keller Williams Realty Boston Northwest
1/38 38

Open Sat 12PM-1PM

$ 1,899,000

4 Beds2.5 Baths3,757 SqFt

85 High St, Winchester, MA 01890

Single Family Home

Listed by Catherine Albiani of Better Homes and Gardens Real Estate - The Shanahan Group
1/36 36

Open Sat 12:30PM-1:30PM

$ 3,600,000

7 Beds7.5 Baths7,429 SqFt

11 Viking Road, Winchester, MA 01890

Single Family Home

Listed by Post Advisory Group of Engel & Volkers Boston
3D

Open Sun 11:30AM-1PM

$ 1,749,000

3 Beds3.5 Baths3,010 SqFt

1 Town Way, Winchester, MA 01890

Single Family Home

Listed by Vita Realty Group of Compass
1/42 42

Open Sat 12PM-1PM

$ 685,000

2 Beds2 Baths1,170 SqFt

666 Main Street #211, Winchester, MA 01890

Condo

Listed by Elizabeth Darby of Berkshire Hathaway HomeServices Commonwealth Real Estate
1/36 36

Open Sat 11AM-12PM

$ 2,100,000

6 Beds4 Baths3,403 SqFt

6 Ivy Circle, Winchester, MA 01890

Single Family Home

Listed by Post Advisory Group of Engel & Volkers Boston
1/40 40

New

$ 3,799,000

8 Beds5 Baths7,081 SqFt

15 Foxcroft Rd, Winchester, MA 01890

Single Family Home

Listed by Karen S. Garrett of Better Homes and Gardens Real Estate - The Shanahan Group
1/24 24

New

$ 3,600

3 Beds2 Baths1,600 SqFt

38-40 Florence Street #2, Winchester, MA 01890

Multi-Family, Townhouse

Listed by WINN Rental Team of WINN Real Estate & Consulting
1/11 11

New

$ 2,600

2 Beds1 Bath800 SqFt

200 Swanton St #635, Winchester, MA 01890

Condo

Listed by Joan Powell of REMAX Andrew Realty Services
1/41 41

New

$ 2,950,000

6 Beds4 Baths4,752 SqFt

18 Surrey Road, Winchester, MA 01890

Single Family Home

Listed by Mary Kelly of Century 21 Property Central Inc.
1/22 22

New

$ 1,125,000

3 Beds1.5 Baths1,684 SqFt

8 Stone Ave, Winchester, MA 01890

Single Family Home

Listed by Lesley Smith of Barrett Sotheby's International Realty
1/40 40

Pending

$ 1,599,000

3 Beds2 Baths2,966 SqFt

4 Harrington Road, Winchester, MA 01890

Single Family Home

Listed by Vita Realty Group of Compass
1/23 23

New

$ 4,500

4 Beds2.5 Baths1,719 SqFt

258 Cross Street #0, Winchester, MA 01890

Single Family Home

Listed by Justin Blankenship of Fiv Realty Co