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Winchester, MA - homes for sale
66 of 66 results displayed
- New
$1,699,000Active4 beds 3 baths2,736 sq. ft.3 Sunset Road, Winchester, MA 01890
MLS# 73596720Listed by: Compass - Open Sat, 11am to 12:30pmNew
$1,049,900Active3 beds 2 baths1,783 sq. ft.28 Olive St, Winchester, MA 01890
MLS# 73595417Listed by: The Aland Realty Group LLC - Open Sat, 11am to 12pmNew
$1,049,000Active4 beds 2 baths2,226 sq. ft.16-18 Russell Rd, Winchester, MA 01890
MLS# 73594513Listed by: Keller Williams Realty Boston Northwest - New
$2,999,000Active5 beds 5 baths4,900 sq. ft.5 Forest Cir, Winchester, MA 01890
MLS# 73594545Listed by: Gibson Sotheby's International Realty - New
$1,450,000Active0.51 Acres67-69 Hemingway St, Winchester, MA 01890
MLS# 73595844Listed by: Gibson Sotheby's International Realty - Open Sat, 11am to 12:30pmNew
$2,650,000Active4 beds 5 baths5,233 sq. ft.18 Middlesex St, Winchester, MA 01890
MLS# 73593868Listed by: Coldwell Banker Realty - Boston - New
Listed by BHGRE$3,799,000Active8 beds 6 baths7,081 sq. ft.15 Foxcroft Rd, Winchester, MA 01890
MLS# 73593484Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - Open Sun, 12 to 1pmNew
$1,299,000Active6 beds 2 baths2,946 sq. ft.419-421 Washington St, Winchester, MA 01890
MLS# 73592723Listed by: Coldwell Banker Realty - Lexington - New
$2,950,000Active6 beds 4 baths4,752 sq. ft.18 Surrey Road, Winchester, MA 01890
MLS# 73592433Listed by: Century 21 Property Central Inc. - Open Sun, 2 to 3:30pm
$890,000Active2 beds 1 baths1,489 sq. ft.80 Nelson St, Winchester, MA 01890
MLS# 73591108Listed by: Compass - Open Sat, 12 to 1:30pm
$1,399,000Active3 beds 3 baths1,975 sq. ft.6 Aricia Ln, Winchester, MA 01890
MLS# 73590311Listed by: Gibson Sotheby's International Realty 
$1,985,000Active4 beds 4 baths4,241 sq. ft.30 Surrey Rd, Winchester, MA 01890
MLS# 73589478Listed by: Barrett Sotheby's International Realty
$1,299,000Active3 beds 2 baths2,350 sq. ft.39 Forest St, Winchester, MA 01890
MLS# 73588863Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$1,999,000Active5 beds 4 baths4,063 sq. ft.21 Amberwood Dr, Winchester, MA 01890
MLS# 73588059Listed by: Compass
$329,900Active2 beds 1 baths1,084 sq. ft.20 Arthur St #20, Winchester, MA 01890
MLS# 73587970Listed by: LAER Realty Partners
$850,000Active3 beds 1 baths1,313 sq. ft.39 Henry Street, Winchester, MA 01890
MLS# 73585414Listed by: Coldwell Banker Realty - Belmont
$18,000,000Active6 beds 7 baths10,000 sq. ft.15 Vinson Circle, Winchester, MA 01890
MLS# 73585235Listed by: The Marino Group Collection
$3,299,000Active7 beds 8 baths7,226 sq. ft.1 Plymouth Rd., Winchester, MA 01890
MLS# 73585058Listed by: Gibson Sotheby's International Realty
$1,529,000Active4 beds 4 baths2,709 sq. ft.25 Arlington St, Winchester, MA 01890
MLS# 73584817Listed by: Coldwell Banker Realty - Lexington- Open Sun, 12 to 1:30pm
Listed by BHGRE$1,750,000Active4 beds 3 baths3,604 sq. ft.1 Overlook Way, Winchester, MA 01890
MLS# 73581571Listed by: Better Homes and Gardens Real Estate - The Shanahan Group 
$700,000Active2 beds 2 baths1,240 sq. ft.666 Main Street #217, Winchester, MA 01890
MLS# 73581469Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$1,325,000Active4 beds 2 baths1,922 sq. ft.9 Priscilla Ln, Winchester, MA 01890
MLS# 73579538Listed by: Compass
$399,000Active1 beds 1 baths613 sq. ft.200 Swanton St #727, Winchester, MA 01890
MLS# 73579389Listed by: Shore Real Estate LLC
$2,400,000Active6 beds 4 baths3,534 sq. ft.7 Lakeview Terrace, Winchester, MA 01890
MLS# 73578443Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$495,000Active2 beds 1 baths822 sq. ft.200 Swanton St #303, Winchester, MA 01890
MLS# 73578112Listed by: Redfin Corp.
$3,200,000Active8 beds 7 baths5,750 sq. ft.30 Willowdale Rd, Winchester, MA 01890
MLS# 73577116Listed by: Gibson Sotheby's International Realty
$974,900Active3 beds 3 baths1,719 sq. ft.258 Cross St, Winchester, MA 01890
MLS# 73575764Listed by: Fiv Realty Co- Open Sun, 12 to 1:30pm
$765,000Active3 beds 2 baths1,643 sq. ft.189 Washington St #2, Winchester, MA 01890
MLS# 73575116Listed by: Compass 
$1,250,000Active4 beds 3 baths2,666 sq. ft.465 Washington Street, Winchester, MA 01890
MLS# 73574928Listed by: Gibson Sotheby's International Realty- Open Sun, 1 to 2pm
$4,299,000Active5 beds 6 baths6,526 sq. ft.4 Dartmouth, Winchester, MA 01890
MLS# 73574948Listed by: Gibson Sotheby's International Realty 
$3,149,000Active7 beds 8 baths8,540 sq. ft.37 Mayflower Road, Winchester, MA 01890
MLS# 73573670Listed by: Compass- Open Sun, 12 to 1:30pm
Listed by BHGRE$1,650,000Active5 beds 4 baths3,722 sq. ft.117 Highland, Winchester, MA 01890
MLS# 73573887Listed by: Better Homes and Gardens Real Estate - The Shanahan Group 
$1,749,000Active5 beds 4 baths3,508 sq. ft.17 Churchill Rd, Winchester, MA 01890
MLS# 73572890Listed by: Coldwell Banker Realty - Lexington
$2,199,000Active4 beds 4 baths3,570 sq. ft.19 Hancock Street, Winchester, MA 01890
MLS# 73572955Listed by: Compass
$660,000Active2 beds 2 baths1,190 sq. ft.60 Lake St #E, Winchester, MA 01890
MLS# 73572854Listed by: Coldwell Banker Realty - Boston
$1,599,000Active4 beds 2 baths2,421 sq. ft.4 Churchill Road, Winchester, MA 01890
MLS# 73572661Listed by: Compass- Open Sat, 12:30 to 1:30pm
$1,049,000Active4 beds 3 baths2,411 sq. ft.24 Richardson St, Winchester, MA 01890
MLS# 73571480Listed by: Keller Williams Realty Boston Northwest 
$1,050,000Active5 beds 3 baths2,801 sq. ft.257 Cross Street, Winchester, MA 01890
MLS# 73571418Listed by: Compass
$1,098,000Active3 beds 2 baths1,657 sq. ft.17 Russell Rd, Winchester, MA 01890
MLS# 73566405Listed by: Kwan Realty Inc.
Listed by BHGRE$1,899,000Active4 beds 3 baths3,757 sq. ft.85 High St, Winchester, MA 01890
MLS# 73565817Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$1,289,000Active3 beds 3 baths2,459 sq. ft.110 Thornberry Road, Winchester, MA 01890
MLS# 73562273Listed by: Kiklis Real Estate, LLC
$2,299,000Active4 beds 5 baths4,450 sq. ft.54 Squire Road, Winchester, MA 01890
MLS# 73555666Listed by: The Marino Group Collection
$919,999Active4 beds 2 baths2,326 sq. ft.96 Loring Ave, Winchester, MA 01890
MLS# 73561829Listed by: StartPoint Realty
$3,450,000Active6 beds 5 baths5,735 sq. ft.7 Hutchinson Road, Winchester, MA 01890
MLS# 73561703Listed by: Compass
$3,200,000Active5 beds 6 baths5,295 sq. ft.18 Ridge St, Winchester, MA 01890
MLS# 73561372Listed by: Compass
$1,549,000Active3 beds 3 baths2,640 sq. ft.50 Holland Street, Winchester, MA 01890
MLS# 73556633Listed by: Compass
$3,600,000Active7 beds 8 baths7,429 sq. ft.11 Viking Road, Winchester, MA 01890
MLS# 73556474Listed by: Engel & Volkers Boston
$1,999,000Active4 beds 4 baths3,640 sq. ft.7 Wainwright Road #113, Winchester, MA 01890
MLS# 73556476Listed by: Compass
$1,749,000Active3 beds 4 baths3,010 sq. ft.1 Town Way, Winchester, MA 01890
MLS# 73555777Listed by: Compass
$664,000Active2 beds 2 baths1,170 sq. ft.666 Main Street #211, Winchester, MA 01890
MLS# 73553517Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$899,000Active3 beds 2 baths1,356 sq. ft.47 Water Street, Winchester, MA 01890
MLS# 73549935Listed by: Leading Edge Real Estate
$600,000Active3 beds 3 baths1,494 sq. ft.247 Washington St #11, Winchester, MA 01890
MLS# 73549877Listed by: Coldwell Banker Realty - Lexington
$769,000Active2 beds 2 baths1,036 sq. ft.50 Middlesex Street #50, Winchester, MA 01890
MLS# 73546074Listed by: Keller Williams Realty Evolution
$2,175,000Active5 beds 3 baths4,071 sq. ft.9 Plymouth Rd, Winchester, MA 01890
MLS# 73544924Listed by: Real Broker MA, LLC
$1,025,000Active3 beds 3 baths2,235 sq. ft.53 Lake Street, Winchester, MA 01890
MLS# 73519082Listed by: Compass
$1,110,000Active5 beds 3 baths2,186 sq. ft.63-65 Harvard Street, Winchester, MA 01890
MLS# 73515601Listed by: Keller Williams Realty Boston Northwest
$2,100,000Active6 beds 5 baths3,403 sq. ft.6 Ivy Circle, Winchester, MA 01890
MLS# 73510713Listed by: Engel & Volkers Boston
$349,900Active1 beds 1 baths613 sq. ft.200 Swanton St #717, Winchester, MA 01890
MLS# 73500952Listed by: Coldwell Banker Realty - Lexington
$2,750,000Active6 beds 7 baths6,968 sq. ft.14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting
Listed by BHGRE$950,000Active2 beds 2 baths1,365 sq. ft.83 Church Street #15, Winchester, MA 01890
MLS# 73497739Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$450,000Active2 beds 1 baths810 sq. ft.200 Swanton Street #T35, Winchester, MA 01890
MLS# 73496844Listed by: Tirana Real Estate Group
$2,195,000Active5 beds 4 baths5,006 sq. ft.276 High Street, Winchester, MA 01890
MLS# 73496396Listed by: Compass
$3,200,000Active6 beds 6 baths6,100 sq. ft.9 Albamont Road, Winchester, MA 01890
MLS# 73482275Listed 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 Shanahan Group
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© 2026 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.
Protect your home and budget from life's surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans.
© 2026 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.