Winchester, MA Homes & Real Estate for Sale

Page 5 of 6
105 listings
257 High Street, Winchester, MA 01890
Single-Family Home For Sale

$3,299,000

  • 5 bed |
  • 7 bath |
  • 7,101 sqft |
  • 1.68 acre lot
257 High Street Winchester, MA 01890

#73426449 - Compass

20 Amberwood Dr, Winchester, MA 01890
Single-Family Home For Sale

$3,600,000

  • 6 bed |
  • 7 bath |
  • 8,866 sqft |
  • 0.53 acre lot
20 Amberwood Dr Winchester, MA 01890

#73423693 - WW Real Estate LLC

52 North Border Rd. 52, Winchester, MA 01890
Rental Available

$11,000 /mo

  • 6 bed |
  • 5 bath |
  • 5,000 sqft |
52 North Border Rd. 52 Winchester, MA 01890

#73423296 - Archambault Real Estate

171 Swanton St 73, Winchester, MA 01890
Pending

$715,000

  • 2 bed |
  • 3 bath |
  • 1,596 sqft |
171 Swanton St 73 Winchester, MA 01890

#73420948 - JMR Real Estate Group LLC

2 Stratton Dr 102, Woburn, MA 01801
Condominium For Sale

$789,900

  • 2 bed |
  • 2 bath |
  • 1,424 sqft |
2 Stratton Dr 102 Woburn, MA 01801

#73421024 - Leading Edge Real Estate

2 George Road 2, Winchester, MA 01890
Condominium For Sale

$662,500

  • 3 bed |
  • 2 bath |
  • 1,232 sqft |
2 George Road 2 Winchester, MA 01890

#73420808 - Coldwell Banker Realty - Lexington

19 Glengarry Road, Winchester, MA 01890
Pending

$1,975,000

  • 6 bed |
  • 4 bath |
  • 3,521 sqft |
  • 0.25 acre lot
19 Glengarry Road Winchester, MA 01890

#73418086 - Compass

7 Thornberry Road, Winchester, MA 01890
Pending

$1,359,000

  • 5 bed |
  • 2 bath |
  • 3,033 sqft |
  • 0.35 acre lot
7 Thornberry Road Winchester, MA 01890

#73417760 - Compass

6 Skillings 2, Winchester, MA 01890
Rental Available

$2,350 /mo

  • 2 bed |
  • 1 bath |
  • 700 sqft |
6 Skillings 2 Winchester, MA 01890

#73415894 - RE/MAX Realty Plus

211 Forest St, Winchester, MA 01890
Rental Available

$7,500 /mo

  • 5 bed |
  • 4 bath |
  • 3,474 sqft |
211 Forest St Winchester, MA 01890

#73414521 - Stuart St James, Inc.

5 Bacon St, Winchester, MA 01890
Pending

$2,190,000

  • 6 bed |
  • 4 bath |
  • 4,385 sqft |
  • 0.25 acre lot
5 Bacon St Winchester, MA 01890

#73411839 - Barrett Sotheby's International Realty

5 Bacon St, Winchester, MA 01890
Pending

$2,190,000

  • 6 bed |
  • 4 bath |
  • 4,385 sqft |
  • 0.25 acre lot
5 Bacon St Winchester, MA 01890

#73412059 - Barrett Sotheby's International Realty

10 Farrow Street, Winchester, MA 01890
Rental Available

$6,450 /mo

  • 4 bed |
  • 4 bath |
  • 3,500 sqft |
10 Farrow Street Winchester, MA 01890

#73407482 - Century 21 Cityside

26 Swan Road, Winchester, MA 01890
Pending

$2,995,000

  • 6 bed |
  • 7 bath |
  • 8,463 sqft |
  • 0.52 acre lot
26 Swan Road Winchester, MA 01890

#73404870 - Compass

276 High Street, Winchester, MA 01890
Single-Family Home For Sale

$2,299,000

  • 5 bed |
  • 4 bath |
  • 5,006 sqft |
  • 0.46 acre lot
276 High Street Winchester, MA 01890

#73404344 - Compass

9 Lakeview Terrace, Winchester, MA 01890
Pending

$3,750,000

  • 6 bed |
  • 4 bath |
  • 4,484 sqft |
9 Lakeview Terrace Winchester, MA 01890

#73390942 - Compass

10 Sheffield Road, Winchester, MA 01890
Pending

$2,799,000

  • 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

$3,999 /mo

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

#73383371 - J. Mulkerin Realty

7 Mckay Ave, Winchester, MA 01890
Commercial Property

$1

  • 2.38 acre lot
7 Mckay Ave Winchester, MA 01890

#73363490 - The Stubblebine Company

19 Cox Road, Winchester, MA 01890
Pending

$1,499,000

  • 3 bed |
  • 2 bath |
  • 2,351 sqft |
  • 0.47 acre lot
19 Cox Road Winchester, MA 01890

#73363545 - Compass

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.

Connect with an Agent
Get paired with a top VA-friendly agentGet an Agent