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Winchester, MA - homes for sale
52 of 52 results displayed
- New
Listed by BHGRE$1,150,000Active4 beds 3 baths2,126 sq. ft.189 High Street, Winchester, MA 01890
MLS# 73451954Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - New
$1,350,000Active3 beds 3 baths2,153 sq. ft.6 Marchant Road, Winchester, MA 01890
MLS# 73451603Listed by: Compass - New
$2,149,000Active5 beds 4 baths4,334 sq. ft.237 Swanton Street, Winchester, MA 01890
MLS# 73451061Listed by: Compass - New
$1,475,000Active3 beds 3 baths2,316 sq. ft.26 Berkshire Dr, Winchester, MA 01890
MLS# 73451080Listed by: OpenDoor Brokerage LLC - New
Listed by BHGRE$1,200,000Active3 beds 3 baths1,942 sq. ft.12 Canterbury Road, Winchester, MA 01890
MLS# 73450862Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - New
$899,900Active0.23 Acres18 Raymond Place, Winchester, MA 01890
MLS# 73450608Listed by: Compass - New
$1,950,000Active1.05 Acres5A Wood Lane, Winchester, MA 01890
MLS# 73450219Listed by: Compass - New
$999,000Active2 beds 2 baths2,033 sq. ft.446 Highland Ave, Winchester, MA 01890
MLS# 73449918Listed by: Keller Williams Realty Boston Northwest - New
$1,950,000Active3 beds 3 baths2,443 sq. ft.5 Wood Lane, Winchester, MA 01890
MLS# 73449729Listed by: Compass - New
$1,499,000Active5 beds 4 baths3,141 sq. ft.209 Washington St #209, Winchester, MA 01890
MLS# 73449686Listed by: Compass - New
$1,499,000Active5 beds 4 baths3,141 sq. ft.209 Washington St, Winchester, MA 01890
MLS# 73449645Listed by: Compass - New
$2,785,000Active4 beds 4 baths5,674 sq. ft.10 Viking Rd, Winchester, MA 01890
MLS# 73449343Listed by: Barrett Sotheby's International Realty - New
$1,549,000Active3 beds 3 baths2,587 sq. ft.32 Woodside Road, Winchester, MA 01890
MLS# 73449320Listed by: Compass - New
Listed by BHGRE$1,650,000Active3 beds 3 baths1,882 sq. ft.82 Hillcrest Parkway, Winchester, MA 01890
MLS# 73448388Listed by: Better Homes and Gardens Real Estate - The Shanahan Group 
$1,199,900Active4 beds 2 baths1,755 sq. ft.102 Hillcrest Pkwy, Winchester, MA 01890
MLS# 73447622Listed by: Howe Realty Group
$1,499,000Active3 beds 4 baths3,807 sq. ft.7 Wainwright Rd #118, Winchester, MA 01890
MLS# 73447418Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$3,250,000Active5 beds 6 baths6,500 sq. ft.8 Priscilla Ln, Winchester, MA 01890
MLS# 73445475Listed by: Rise Signature Homes- New
$385,000Active1 beds 1 baths634 sq. ft.200 Swanton St #T28, Winchester, MA 01890
MLS# 73450853Listed by: RE/MAX Andrew Realty Services 
$2,799,000Active5 beds 4 baths5,083 sq. ft.53 Winford Way, Winchester, MA 01890
MLS# 73444348Listed by: Keller Williams Realty Boston Northwest
$1,499,000Active3 beds 3 baths2,865 sq. ft.53 Bacon Street, Winchester, MA 01890
MLS# 73444073Listed by: Leading Edge Real Estate
$2,275,000Active6 beds 3 baths4,104 sq. ft.15 Wildwood Street, Winchester, MA 01890
MLS# 73443803Listed by: Compass
Listed by BHGRE$1,200,000Active4 beds 2 baths2,004 sq. ft.50 Lincoln Street, Winchester, MA 01890
MLS# 73442848Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$3,199,000Active6 beds 7 baths5,709 sq. ft.39 Town Way, Winchester, MA 01890
MLS# 73442521Listed by: Compass
$1,999,000Active5 beds 4 baths6,232 sq. ft.5 Azalea Road, Winchester, MA 01890
MLS# 73442291Listed by: The Marino Group Collection
$2,795,000Active4 beds 5 baths5,233 sq. ft.18 Middlesex St, Winchester, MA 01890
MLS# 73442182Listed by: Luxury Living Real Estate- Open Sat, 12:30 to 1:30pm
$3,799,000Active6 beds 5 baths6,367 sq. ft.40 Foxcroft Road, Winchester, MA 01890
MLS# 73441255Listed by: Coldwell Banker Realty - Lexington 
$299,000Active1 beds 1 baths394 sq. ft.200 Swanton St #636, Winchester, MA 01890
MLS# 73439236Listed by: North Atlantic Realty Group
$2,349,000Active6 beds 5 baths4,200 sq. ft.14 Grant Rd, Winchester, MA 01890
MLS# 73438521Listed by: Coldwell Banker Realty - Lexington
$1,149,000Active3 beds 3 baths1,844 sq. ft.16 Ridge Street, Winchester, MA 01890
MLS# 73442463Listed by: Compass
$1,285,000Active4 beds 2 baths2,696 sq. ft.104 Church Street, Winchester, MA 01890
MLS# 73435935Listed by: Compass
$949,000Active4 beds 2 baths1,938 sq. ft.380 Cross St, Winchester, MA 01890
MLS# 73429179Listed by: Realty ONE Group Nest
Listed by BHGRE$4,174,000Active7 beds 6 baths7,043 sq. ft.2 Everett Ave, Winchester, MA 01890
MLS# 73427282Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$3,299,000Active5 beds 7 baths7,101 sq. ft.257 High Street, Winchester, MA 01890
MLS# 73426449Listed by: Compass
$389,900Active2 beds 1 baths1,084 sq. ft.20 Arthur St #20, Winchester, MA 01890
MLS# 73425853Listed by: LAER Realty Partners
$3,600,000Active6 beds 7 baths8,866 sq. ft.20 Amberwood Dr, Winchester, MA 01890
MLS# 73423693Listed by: WW Real Estate LLC
$662,500Active3 beds 2 baths1,232 sq. ft.2 George Road #2, Winchester, MA 01890
MLS# 73420808Listed by: Coldwell Banker Realty - Lexington
$1,975,000Active6 beds 4 baths3,521 sq. ft.19 Glengarry Road, Winchester, MA 01890
MLS# 73418086Listed by: Compass
$2,190,000Active6 beds 4 baths4,385 sq. ft.5 Bacon St, Winchester, MA 01890
MLS# 73412059Listed by: Barrett Sotheby's International Realty
$2,190,000Active6 beds 4 baths4,385 sq. ft.5 Bacon St, Winchester, MA 01890
MLS# 73411839Listed by: Barrett Sotheby's International Realty
$2,299,000Active5 beds 4 baths5,006 sq. ft.276 High Street, Winchester, MA 01890
MLS# 73404344Listed by: Compass
$1,869,000Active5 beds 4 baths3,294 sq. ft.20 Grove Pl, Winchester, MA 01890
MLS# 73404144Listed by: Keller Williams Realty Boston Northwest
$2,239,000Active5 beds 5 baths4,798 sq. ft.61 Grove Street, Winchester, MA 01890
MLS# 73399772Listed by: Coldwell Banker Realty - Lexington
$1,990,000Active4 beds 5 baths4,474 sq. ft.4 Chestnut St, Winchester, MA 01890
MLS# 73396909Listed by: The Proper Nest Real Estate
$3,099,000Active6 beds 7 baths6,028 sq. ft.44 Cabot Street, Winchester, MA 01890
MLS# 73436302Listed by: Keller Williams Realty Boston Northwest
$898,000Active3 beds 1 baths1,425 sq. ft.571 Washington St, Winchester, MA 01890
MLS# 73428179Listed by: Keller Williams Realty
Listed by BHGRE$3,099,000Active5 beds 4 baths5,632 sq. ft.80 Arlington St, Winchester, MA 01890
MLS# 73438221Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$2,850,000Active6 beds 7 baths6,968 sq. ft.14 Nassau Drive, Winchester, MA 01890
MLS# 73434748Listed by: WINN Real Estate & Consulting
$2,000,000Active6 beds 4 baths4,696 sq. ft.5 Squire Rd, Winchester, MA 01890
MLS# 73356942Listed by: Coldwell Banker Realty - Lexington
$3,499,000Active7 beds 8 baths7,982 sq. ft.54 Johnson Road, Winchester, MA 01890
MLS# 73335471Listed by: Compass
$949,900Active4 beds 3 baths1,880 sq. ft.116 Forest St, Winchester, MA 01890
MLS# 73179157Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$2,799,000Active5 beds 6 baths6,067 sq. ft.10 North Gateway, Winchester, MA 01890
MLS# 73158946Listed by: Compass
$2,799,000Active5 beds 5 baths5,000 sq. ft.1 Alice Lane, Winchester, MA 01890
MLS# 73107072Listed by: Compass
Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
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Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.
Protect your home and budget with an American Home Shield© home warranty. Learn more© 2025 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.