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Winchester, MA - homes for sale
56 of 56 results displayed
- Open Sat, 11am to 12:30pmNew
$1,549,000Active3 beds 3 baths2,640 sq. ft.50 Holland Street, Winchester, MA 01890
MLS# 73556633Listed by: Compass - Open Sat, 11:30am to 1pmNew
$3,600,000Active7 beds 8 baths7,429 sq. ft.11 Viking Road, Winchester, MA 01890
MLS# 73556474Listed by: Engel & Volkers Boston - Open Sat, 1 to 2:30pmNew
$2,100,000Active4 beds 4 baths3,640 sq. ft.7 Wainwright Road #113, Winchester, MA 01890
MLS# 73556476Listed by: Compass - Open Sat, 12 to 1:30pmNew
$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 - Open Sun, 11:30am to 1pmNew
$1,799,000Active3 beds 4 baths3,010 sq. ft.1 Town Way, Winchester, MA 01890
MLS# 73555777Listed by: Compass - Open Sat, 12 to 1:30pmNew
$1,125,000Active5 beds 3 baths2,391 sq. ft.8 Oak Street, Winchester, MA 01890
MLS# 73555597Listed by: The Synergy Group - Open Sat, 12 to 1:30pmNew
$1,125,000Active5 beds 3 baths2,391 sq. ft.8-10 Oak St, Winchester, MA 01890
MLS# 73555245Listed by: The Synergy Group - New
$2,225,000Active4 beds 4 baths4,210 sq. ft.6 Davey Ln, Winchester, MA 01890
MLS# 73554545Listed by: Coldwell Banker Realty - Andovers/Readings Regional - New
$1,150,000Active4 beds 3 baths2,392 sq. ft.11 Williams Cir, Winchester, MA 01890
MLS# 73554139Listed by: Barrett Sotheby's International Realty - New
$849,000Active3 beds 2 baths1,340 sq. ft.15 Clark St, Winchester, MA 01890
MLS# 73555218Listed by: Coldwell Banker Realty - Milton - New
$700,000Active2 beds 2 baths1,170 sq. ft.666 Main #211, Winchester, MA 01890
MLS# 73553517Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate - Open Sat, 11am to 12pmNew
$1,099,000Active5 beds 3 baths2,801 sq. ft.257 Cross St, Winchester, MA 01890
MLS# 73553083Listed 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, 11am to 12pm
$729,000Active3 beds 3 baths1,494 sq. ft.247 Washington St #11, Winchester, MA 01890
MLS# 73549877Listed by: Coldwell Banker Realty - Lexington 
$1,150,000Active3 beds 3 baths2,004 sq. ft.52 Salem Street #52, Winchester, MA 01890
MLS# 73549484Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$288,750Active1 beds 1 baths388 sq. ft.200 Swanton #L8, Winchester, MA 01890
MLS# 73548413Listed by: Cameron Real Estate Group- Open Sun, 1 to 2pm
$2,999,000Active5 beds 4 baths4,028 sq. ft.10 Dartmouth Street, Winchester, MA 01890
MLS# 73548103Listed by: Compass - Open Sat, 11am to 12pm
$1,064,000Active4 beds 2 baths1,777 sq. ft.46 Clark St, Winchester, MA 01890
MLS# 73547513Listed by: Keller Williams Realty Boston Northwest - Open Sat, 11am to 1pmNew
$1,599,000Active4 beds 4 baths2,480 sq. ft.241 Ridge St, Winchester, MA 01890
MLS# 73554036Listed by: Lillian Montalto Signature Properties - Open Sat, 11am to 1pm
$799,000Active2 beds 2 baths1,036 sq. ft.50 Middlesex Street #50, Winchester, MA 01890
MLS# 73546074Listed by: Keller Williams Realty Evolution - 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 - Open Sun, 12:30 to 1:30pm
$2,500,000Active5 beds 3 baths4,071 sq. ft.9 Plymouth Rd, Winchester, MA 01890
MLS# 73544924Listed by: Real Broker MA, LLC 
$649,900Active2 beds 2 baths1,025 sq. ft.666 Main Street #315, Winchester, MA 01890
MLS# 73543744Listed by: Compass- Open Sat, 11:30am to 1pm
$888,000Active4 beds 2 baths2,083 sq. ft.84 Oak Street, Winchester, MA 01890
MLS# 73542597Listed by: Charlesgate Realty Group LLC 
$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- Open Sun, 2 to 3:30pm
$2,300,000Active4 beds 5 baths3,881 sq. ft.14 Hillside Ave, Winchester, MA 01890
MLS# 73541163Listed by: William Raveis R.E. & Home Services 
$1,099,000Active3 beds 2 baths1,711 sq. ft.150 Cambridge Street, Winchester, MA 01890
MLS# 73530959Listed by: Plunkett Properties- Open Sun, 12:30 to 2pm
$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 - Open Sun, 11am to 12pm
$2,099,000Active4 beds 4 baths3,210 sq. ft.26 N Gateway, Winchester, MA 01890
MLS# 73538052Listed by: Gibson Sotheby's International Realty - Open Sun, 1 to 2pm
$1,175,000Active3 beds 3 baths1,736 sq. ft.38 Robinhood Rd, Winchester, MA 01890
MLS# 73537786Listed by: Better Homes and Gardens Real Estate - The Shanahan Group 
$3,199,000Active5 beds 5 baths5,406 sq. ft.10 Rangeley Road, Winchester, MA 01890
MLS# 73535697Listed by: Compass
$1,299,000Active3 beds 3 baths2,145 sq. ft.7 Wainwright Road #47, Winchester, MA 01890
MLS# 73534894Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$1,899,000Active6 beds 5 baths6,900 sq. ft.16 Glenwood Ave, Winchester, MA 01890
MLS# 73507145Listed by: Compass
$1,899,000Active6 beds 5 baths6,900 sq. ft.16 & 16A Glenwood Ave, Winchester, MA 01890
MLS# 73507137Listed by: Compass
$2,499,000Active5 beds 4 baths5,230 sq. ft.78 Bacon Street, Winchester, MA 01890
MLS# 73526460Listed by: Compass- Open Sat, 12:30 to 1:30pm
$2,399,000Active5 beds 4 baths5,083 sq. ft.53 Winford Way, Winchester, MA 01890
MLS# 73525195Listed by: Keller Williams Realty Boston Northwest 
$499,999Active2 beds 1 baths822 sq. ft.200 Swanton St #303, Winchester, MA 01890
MLS# 73524262Listed by: REMAX Andrew Realty Services
$1,825,000Active5 beds 4 baths3,315 sq. ft.8 Hawthorne Road, Winchester, MA 01890
MLS# 73522773Listed by: Coldwell Banker Realty - Lexington- Open Sun, 1 to 2pm
$1,199,000Active3 beds 3 baths2,235 sq. ft.53 Lake Street, Winchester, MA 01890
MLS# 73519082Listed by: Compass 
$2,795,000Active4 beds 5 baths5,233 sq. ft.18 Middlesex St, Winchester, MA 01890
MLS# 73518621Listed by: Luxury Living Real Estate
$1,150,000Active5 beds 3 baths2,186 sq. ft.63-65 Harvard Street, Winchester, MA 01890
MLS# 73515601Listed by: Keller Williams Realty Boston Northwest- 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 - Open Sat, 1:30 to 3pm
$1,099,000Active3 beds 4 baths2,420 sq. ft.129 Washington St #129, Winchester, MA 01890
MLS# 73513572Listed by: Leading Edge Real Estate 
$3,179,000Active7 beds 8 baths8,540 sq. ft.37 Mayflower Road, Winchester, MA 01890
MLS# 73502853Listed by: Compass
$349,900Active1 beds 1 baths613 sq. ft.200 Swanton St #717, Winchester, MA 01890
MLS# 73500952Listed by: Coldwell Banker Realty - Lexington
$2,799,000Active6 beds 7 baths6,968 sq. ft.14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting
$929,900Active4 beds 2 baths1,938 sq. ft.380 Cross Street, Winchester, MA 01890
MLS# 73498603Listed by: Coldwell Banker Realty - Lexington- Open Sun, 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 - Open Sun, 11:30am to 12:30pm
$999,000Active2 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
$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:CENTURY 21 The Real Estate Group
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©2026 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.
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 Century 21 Real Estate LLC. All rights reserved. CENTURY 21®, the CENTURY 21 Logo and C21® are service marks owned by Century 21 Real Estate LLC. Century 21 Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Each office is independently owned and operated. Listing information is deemed reliable but not guaranteed accurate.