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Winchester, MA - homes for sale
52 of 52 results displayed
- New
$1,799,000Active4 beds 3 baths2,818 sq. ft.12 Cox Rd, Winchester, MA 01890
MLS# 73511596Listed by: RE/MAX Bentley's - New
Listed by BHGRE$2,299,000Active5 beds 4 baths4,822 sq. ft.216 Highland Avenue, Winchester, MA 01890
MLS# 73511014Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - New
$3,099,000Active5 beds 5 baths5,406 sq. ft.10 Rangeley Road, Winchester, MA 01890
MLS# 73511033Listed by: Compass - New
$2,595,000Active4 beds 4 baths4,403 sq. ft.50 Brooks Street, Winchester, MA 01890
MLS# 73510897Listed by: Compass - New
$2,750,000Active7 beds 4 baths3,676 sq. ft.15 Yale St, Winchester, MA 01890
MLS# 73510619Listed by: Compass - New
$2,000,000Active6 beds 5 baths3,403 sq. ft.6 Ivy Circle, Winchester, MA 01890
MLS# 73510713Listed by: Engel & Volkers Boston - New
Listed by BHGRE$2,500,000Active5 beds 4 baths4,500 sq. ft.15 York Road, Winchester, MA 01890
MLS# 73510389Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - New
$649,000Active3 beds 2 baths1,300 sq. ft.2 George Road #2, Winchester, MA 01890
MLS# 73510206Listed by: Compass - New
$1,250,000Active5 beds 2 baths2,688 sq. ft.6 Hancock St, Winchester, MA 01890
MLS# 73510153Listed by: Gibson Sotheby's International Realty - New
$2,490,000Active6 beds 4 baths4,573 sq. ft.7 Cliff Street, Winchester, MA 01890
MLS# 73509698Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate - New
$899,000Active3 beds 2 baths1,799 sq. ft.9 Governors Avenue #2, Winchester, MA 01890
MLS# 73509305Listed by: Compass - New
$1,299,000Active3 beds 2 baths2,030 sq. ft.12 Hancock St, Winchester, MA 01890
MLS# 73508959Listed by: Compass - New
$1,399,000Active3 beds 4 baths2,936 sq. ft.71 Sargent Road, Winchester, MA 01890
MLS# 73501230Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate - New
Listed by BHGRE$1,700,000Active5 beds 5 baths3,500 sq. ft.307 Cross Street, Winchester, MA 01890
MLS# 73508927Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - New
$1,800,000Active2 beds 4 baths3,874 sq. ft.10 Graystone Cir #10, Winchester, MA 01890
MLS# 73508182Listed by: Gibson Sotheby's International Realty - New
$2,200,000Active6 beds 5 baths6,900 sq. ft.16 Glenwood Ave, Winchester, MA 01890
MLS# 73507145Listed by: Compass - New
$725,000Active2 beds 2 baths1,588 sq. ft.7 Conant Road #53, Winchester, MA 01890
MLS# 73507003Listed by: Compass - New
$2,699,000Active5 beds 4 baths5,950 sq. ft.21 Bellevue Avenue, Winchester, MA 01890
MLS# 73506730Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate - New
$1,349,000Active3 beds 2 baths2,355 sq. ft.205 Washington St., Winchester, MA 01890
MLS# 73503540Listed by: Coldwell Banker Realty - Boston 
$1,549,000Active4 beds 3 baths3,298 sq. ft.6 Oakland Circle, Winchester, MA 01890
MLS# 73505351Listed by: Coldwell Banker Realty - Lexington
$3,379,000Active7 beds 8 baths8,540 sq. ft.37 Mayflower Road, Winchester, MA 01890
MLS# 73502853Listed by: Compass
$364,900Active1 beds 1 baths613 sq. ft.200 Swanton St #717, Winchester, MA 01890
MLS# 73500952Listed by: Coldwell Banker Realty - Lexington
$2,850,000Active6 beds 7 baths6,968 sq. ft.14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting
$1,199,000Active4 beds 2 baths2,129 sq. ft.31 Mystic Ave #31, Winchester, MA 01890
MLS# 73499537Listed by: Compass
$3,299,000Active5 beds 5 baths5,202 sq. ft.74 Wedgemere Avenue, Winchester, MA 01890
MLS# 73499151Listed by: Compass
$2,800,000Active4 beds 5 baths3,945 sq. ft.2 Edgewater Place, Winchester, MA 01890
MLS# 73498843Listed by: Gibson Sotheby's International Realty
$939,900Active4 beds 2 baths1,938 sq. ft.380 Cross Street, Winchester, MA 01890
MLS# 73498603Listed by: Coldwell Banker Realty - Lexington
$3,399,000Active7 beds 8 baths7,226 sq. ft.1 Plymouth Rd, Winchester, MA 01890
MLS# 73498293Listed by: Douglas Elliman Real Estate - The Sarkis Team
$1,899,999Active4 beds 3 baths3,512 sq. ft.94 Johnson Road, Winchester, MA 01890
MLS# 73497889Listed by: Compass
Listed by BHGRE$1,100,000Active2 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
$400,000Active2 beds 1 baths810 sq. ft.200 Swanton Street #T35, Winchester, MA 01890
MLS# 73496844Listed by: Tirana Real Estate Group
$727,000Active2 beds 1 baths1,029 sq. ft.115 Washington Street #2A, Winchester, MA 01890
MLS# 73496388Listed by: Compass
$2,299,000Active5 beds 4 baths5,006 sq. ft.276 High Street, Winchester, MA 01890
MLS# 73496396Listed by: Compass
$2,999,000Active5 beds 4 baths4,028 sq. ft.10 Dartmouth Street, Winchester, MA 01890
MLS# 73496399Listed by: Compass
$279,000Active-- beds 1 baths394 sq. ft.200 Swanton St #538, Winchester, MA 01890
MLS# 73496212Listed by: North Atlantic Realty Group
$1,099,000Active3 beds 2 baths1,973 sq. ft.15 East Street, Winchester, MA 01890
MLS# 73493684Listed by: Compass
Listed by BHGRE$3,747,000Active7 beds 6 baths7,043 sq. ft.2 Everett Ave, Winchester, MA 01890
MLS# 73488991Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$3,650,000Active6 beds 5 baths6,460 sq. ft.40 Foxcroft Rd, Winchester, MA 01890
MLS# 73485774Listed by: Serhant
$4,449,000Active5 beds 6 baths6,526 sq. ft.4 Dartmouth St, Winchester, MA 01890
MLS# 73482952Listed by: Gibson Sotheby's International Realty
$3,400,000Active6 beds 6 baths6,100 sq. ft.9 Albamont Road, Winchester, MA 01890
MLS# 73482275Listed by: Compass
$1,095,000Active5 beds 2 baths2,331 sq. ft.149 Horn Pond Brook Road, Winchester, MA 01890
MLS# 73478668Listed by: Redfin Corp.
$3,390,000Active4 beds 4 baths4,847 sq. ft.25 Myopia Road, Winchester, MA 01890
MLS# 73471735Listed by: Engel & Volkers Boston
$1,874,000Active3 beds 4 baths3,010 sq. ft.1 Town Way, Winchester, MA 01890
MLS# 73466233Listed by: Compass
$688,000Active2 beds 2 baths1,025 sq. ft.666 Main St #315, Winchester, MA 01890
MLS# 73485732Listed by: Peace of Mind Realty
$375,000Active1 beds 1 baths606 sq. ft.200 Swanton St #228, Winchester, MA 01890
MLS# 73459781Listed by: RE/MAX Andrew Realty Services
$2,799,000Active5 beds 4 baths5,083 sq. ft.53 Winford Way, Winchester, MA 01890
MLS# 73481323Listed by: Keller Williams Realty Boston Northwest
$3,600,000Active6 beds 7 baths8,866 sq. ft.20 Amberwood Dr, Winchester, MA 01890
MLS# 73423693Listed by: WW Real Estate LLC
$3,290,000Active6 beds 6 baths7,431 sq. ft.27 Everett Ave, Winchester, MA 01890
MLS# 73468691Listed by: Gibson Sotheby's International Realty
$3,499,000Active5 beds 8 baths6,899 sq. ft.54 Johnson Rd, Winchester, MA 01890
MLS# 73474290Listed 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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© 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.