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Winchester, MA - single-family homes for sale
37 of 37 results displayed
- Open Sat, 12:30 to 2pmNew
$3,295,000Active6 beds 7 baths6,100 sq. ft.2 Atherton Rd, Winchester, MA 01890
MLS# 73563095Listed by: Serhant - Open Sat, 1:30 to 3pmNew
$1,529,000Active3 beds 3 baths1,956 sq. ft.20 Sargent Rd, Winchester, MA 01890
MLS# 73562422Listed by: Barrett Sotheby's International Realty - Open Sat, 11am to 1pmNew
$1,499,995Active3 beds 3 baths2,459 sq. ft.110 Thornberry Road, Winchester, MA 01890
MLS# 73562273Listed by: Kiklis Real Estate, LLC - Open Sat, 1 to 2:30pmNew
$2,499,000Active4 beds 5 baths4,450 sq. ft.54 Squire Road, Winchester, MA 01890
MLS# 73555666Listed by: The Marino Group Collection - Open Sat, 11am to 12:30pmNew
$3,450,000Active6 beds 5 baths5,735 sq. ft.7 Hutchinson Road, Winchester, MA 01890
MLS# 73561703Listed by: Compass - New
$3,200,000Active5 beds 6 baths5,295 sq. ft.18 Ridge St, Winchester, MA 01890
MLS# 73561372Listed by: Compass - New
$2,999,000Active4 beds 4 baths4,500 sq. ft.5 Forest Cir, Winchester, MA 01890
MLS# 73560088Listed by: Gibson Sotheby's International Realty - Open Sat, 11:30am to 12:30pm
$1,549,000Active3 beds 3 baths2,640 sq. ft.50 Holland Street, Winchester, MA 01890
MLS# 73556633Listed by: Compass - Open Sat, 1 to 2:30pm
$3,600,000Active7 beds 8 baths7,429 sq. ft.11 Viking Road, Winchester, MA 01890
MLS# 73556474Listed by: Engel & Volkers Boston - Open Sat, 12 to 1:30pm
Listed by BHGRE$2,299,000Active7 beds 5 baths4,930 sq. ft.42 Wildwood Street, Winchester, MA 01890
MLS# 73556122Listed by: Better Homes and Gardens Real Estate - The Shanahan Group 
$1,794,000Active3 beds 4 baths3,010 sq. ft.1 Town Way, Winchester, MA 01890
MLS# 73555777Listed by: Compass
$950,000Active3 beds 1 baths1,356 sq. ft.47 Water Street, Winchester, MA 01890
MLS# 73549935Listed by: Leading Edge Real Estate- Open Sat, 1 to 2pm
$2,999,000Active5 beds 4 baths4,028 sq. ft.10 Dartmouth Street, Winchester, MA 01890
MLS# 73548103Listed by: Compass - Open Sat, 12:30 to 1:30pm
$1,064,000Active4 beds 2 baths1,777 sq. ft.46 Clark St, Winchester, MA 01890
MLS# 73547513Listed by: Keller Williams Realty Boston Northwest - Open Sun, 11am to 1pm
$1,599,000Active4 beds 4 baths2,480 sq. ft.241 Ridge St, Winchester, MA 01890
MLS# 73554036Listed by: Lillian Montalto Signature Properties - Open Sat, 12 to 1:30pm
$1,899,000Active5 beds 4 baths3,210 sq. ft.79 Grove St, Winchester, MA 01890
MLS# 73545952Listed by: Gibson Sotheby's International Realty 
$2,500,000Active5 beds 3 baths4,071 sq. ft.9 Plymouth Rd, Winchester, MA 01890
MLS# 73544924Listed by: Real Broker MA, LLC- Open Sat, 12 to 1:30pm
$849,000Active4 beds 2 baths2,083 sq. ft.84 Oak Street, Winchester, MA 01890
MLS# 73542597Listed by: Charlesgate Realty Group LLC - Open Sun, 12 to 1pm
$1,350,000Active4 beds 3 baths2,690 sq. ft.423 Washington St, Winchester, MA 01890
MLS# 73541775Listed by: MA Properties 
$999,900Active4 beds 2 baths1,719 sq. ft.258 Cross Street, Winchester, MA 01890
MLS# 73541288Listed by: Fiv Realty Co
$1,099,000Active3 beds 2 baths1,711 sq. ft.150 Cambridge Street, Winchester, MA 01890
MLS# 73530959Listed by: Plunkett Properties- Open Sun, 12 to 1:30pm
Listed by BHGRE$1,675,000Active5 beds 4 baths3,722 sq. ft.117 Highland Ave, Winchester, MA 01890
MLS# 73538393Listed by: Better Homes and Gardens Real Estate - The Shanahan Group 
Listed by BHGRE$1,125,000Active3 beds 3 baths1,736 sq. ft.38 Robinhood Rd, Winchester, MA 01890
MLS# 73537786Listed by: Better Homes and Gardens Real Estate - The Shanahan Group- Open Sun, 11:30am to 1pm
$1,925,000Active4 beds 4 baths3,286 sq. ft.15 Fieldstone Dr, Winchester, MA 01890
MLS# 73537676Listed by: Barrett Sotheby's International Realty - Open Sat, 3 to 4pm
$2,399,000Active5 beds 4 baths5,083 sq. ft.53 Winford Way, Winchester, MA 01890
MLS# 73525195Listed by: Keller Williams Realty Boston Northwest - Open Sat, 11am to 12pm
$1,150,000Active3 beds 3 baths2,235 sq. ft.53 Lake Street, Winchester, MA 01890
MLS# 73519082Listed by: Compass 
$2,695,000Active4 beds 5 baths5,233 sq. ft.18 Middlesex St, Winchester, MA 01890
MLS# 73518621Listed by: Luxury Living Real Estate- Open Sat, 12 to 1pm
$3,149,000Active5 beds 6 baths6,500 sq. ft.8 Priscilla Ln, Winchester, MA 01890
MLS# 73513501Listed by: Rise Signature Homes 
$2,100,000Active6 beds 5 baths3,403 sq. ft.6 Ivy Circle, Winchester, MA 01890
MLS# 73510713Listed by: Engel & Volkers Boston
$3,179,000Active7 beds 8 baths8,540 sq. ft.37 Mayflower Road, Winchester, MA 01890
MLS# 73502853Listed by: Compass
$2,799,000Active6 beds 7 baths6,968 sq. ft.14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting- Open Sat, 1 to 2:30pm
$3,299,000Active7 beds 8 baths7,226 sq. ft.1 Plymouth Rd, Winchester, MA 01890
MLS# 73498293Listed by: Douglas Elliman Real Estate - The Sarkis Team 
$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 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.