Winchester, MA Homes & Real Estate for Sale

Page 1 of 8
157 listings
5 Stratford Road, Winchester, MA 01890New listing icon New - 1 day ago
Single-Family Home For Sale

$3,599,000

  • 6 bed |
  • 6 bath |
  • 5,876 sqft |
  • 0.35 acre lot
5 Stratford Road Winchester, MA 01890

#73386552 - Compass

10 Girard Rd, Winchester, MA 01890New listing icon New - 1 day ago
Single-Family Home For Sale

$1,349,000

  • 3 bed |
  • 2 bath |
  • 3,335 sqft |
  • 0.34 acre lot
10 Girard Rd Winchester, MA 01890

#73385982 - Coldwell Banker Realty - Lexington

71-73 George Rd 71, Winchester, MA 01890New listing icon New - 1 day ago
Rental Available

$3,300 /mo

  • 3 bed |
  • 2 bath |
  • 1,400 sqft |
  • 5,663 sqft lot
71-73 George Rd 71 Winchester, MA 01890

#73386187 - Baymaxx Realty, LLC

7 Wainwright Road 55, Winchester, MA 01890New listing icon New - 1 day ago
Condominium For Sale

$1,625,000

  • 3 bed |
  • 4 bath |
  • 4,228 sqft
7 Wainwright Road 55 Winchester, MA 01890

#73386110 - Leading Edge Real Estate

162 Swanton Street 162, Winchester, MA 01890New listing icon New - 1 day ago
Condominium For Sale

$1,299,000

  • 3 bed |
  • 4 bath |
  • 2,136 sqft
162 Swanton Street 162 Winchester, MA 01890

#73386065 - Coldwell Banker Realty - Lexington

9 Prospect St, Winchester, MA 01890New listing icon New - 1 day ago
Single-Family Home For Sale

$2,379,000

  • 5 bed |
  • 4 bath |
  • 4,667 sqft |
  • 0.26 acre lot
9 Prospect St Winchester, MA 01890

#73385985 - Advisors Living - Winchester

273 Cross St 273, Winchester, MA 01890New listing icon New - 2 days ago
Rental Available

$2,800 /mo

  • 2 bed |
  • 2 bath |
  • 1,452 sqft
273 Cross St 273 Winchester, MA 01890

#73385712 - Phoenix Real Estate Partners, LLC

518 Washington St, Winchester, MA 01890New listing icon New - 2 days ago
Single-Family Home For Sale

$1,199,900

  • 4 bed |
  • 3 bath |
  • 2,302 sqft |
  • 5,663 sqft lot
518 Washington St Winchester, MA 01890

#73385500 - Leading Edge Real Estate

44 Amberwood Drive, Winchester, MA 01890New listing icon New - 2 days ago
Single-Family Home For Sale

$1,920,000

  • 3 bed |
  • 3 bath |
  • 3,002 sqft |
  • 0.61 acre lot
44 Amberwood Drive Winchester, MA 01890

#73385650 - Keller Williams Realty Boston Northwest

109 Thornberry Rd, Winchester, MA 01890New listing icon New - 2 days ago
Single-Family Home For Sale

$1,799,000

  • 4 bed |
  • 4 bath |
  • 3,784 sqft |
  • 0.54 acre lot
109 Thornberry Rd Winchester, MA 01890

#73385735 - Compass

21 Fernway, Winchester, MA 01890New listing icon New - 2 days ago
Single-Family Home For Sale

$3,175,000

  • 5 bed |
  • 5 bath |
  • 5,386 sqft |
  • 0.46 acre lot
21 Fernway Winchester, MA 01890

#73385326 - Compass

19 Laurel Hill Ln, Winchester, MA 01890New listing icon New - 2 days ago
Single-Family Home For Sale

$2,550,000

  • 5 bed |
  • 5 bath |
  • 3,800 sqft |
  • 0.31 acre lot
19 Laurel Hill Ln Winchester, MA 01890

#73385211 - Advisors Living - Winchester

35 Rumford St 35, Winchester, MA 01890New listing icon New - 2 days ago
Single-Family Home For Sale

$1,458,000

  • 4 bed |
  • 3 bath |
  • 2,470 sqft |
  • 0.28 acre lot
35 Rumford St 35 Winchester, MA 01890

#73384905 - Compass

35 Rumford St 35, Winchester, MA 01890New listing icon New - 2 days ago
Condominium For Sale

$1,458,000

  • 4 bed |
  • 3 bath |
  • 2,470 sqft
35 Rumford St 35 Winchester, MA 01890

#73384904 - Compass

40 Florence Street 40, Winchester, MA 01890New listing icon New - 2 days ago
Rental Available

$3,300 /mo

  • 2 bed |
  • 1 bath |
  • 1,100 sqft |
  • 6,098 sqft lot
40 Florence Street 40 Winchester, MA 01890

#73384896 - WINN Real Estate & Consulting

5 Hastings Rd, Winchester, MA 01890New listing icon New - 3 days ago
Single-Family Home For Sale

$1,899,000

  • 4 bed |
  • 4 bath |
  • 4,195 sqft |
  • 10,454 sqft lot
5 Hastings Rd Winchester, MA 01890

#73384193 - Advisors Living - Winchester

163 Main St, Winchester, MA 01890New listing icon New - 3 days ago
Single-Family Home For Sale

$999,000

  • 4 bed |
  • 3 bath |
  • 2,335 sqft |
  • 0.25 acre lot
163 Main St Winchester, MA 01890

#73384584 - Keller Williams Realty Boston Northwest

200 Swanton St 428, Winchester, MA 01890
Rental Available

$2,100 /mo

  • 1 bed |
  • 1 bath |
  • 606 sqft |
  • 871 sqft lot
200 Swanton St 428 Winchester, MA 01890

#73384063 - WW Real Estate LLC

10 Sheffield Road, Winchester, MA 01890
Single-Family Home For Sale

$2,899,000

  • 7 bed |
  • 6 bath |
  • 5,864 sqft |
  • 0.28 acre lot
10 Sheffield Road Winchester, MA 01890

#73383662 - Keller Williams Realty Boston Northwest

4 Stratton Drive 301, Woburn, MA 01801
Rental Available

$5,000 /mo

  • 2 bed |
  • 2 bath |
  • 1,667 sqft |
  • 10,019 sqft lot
4 Stratton Drive 301 Woburn, MA 01801

#73383371 - J. Mulkerin Realty

Presented by James Burton - Marathon Real Estate LLC

Veterans United Homefront
IDX Disclaimer: The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein. We may make use of information provided by users of this website - see our Terms of Use for more details on our privacy policy. Data displayed may be a portion of, and not a complete set of all listings published in the MLS.

For questions call 1-833-252-8030

Copyright © 2025 Marathon Real Estate LLC and Did You Serve, LLC. Homefront.com is NOT affiliated with any government agencies, including the VA. Homefront.com is a service of Did You Serve, LLC. Veterans United and the Veterans United House logo are registered trademarks of Mortgage Research Center, LLC, used under license agreement. Terms of Use.