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Winchester, MA - homes for sale
58 of 58 results displayed
- Open Sat, 12 to 2pmNew
$624,900Active3 beds 2 baths1,168 sq. ft.14 Bradford Rd #14, Winchester, MA 01890
MLS# 73538704Listed by: Keller Williams Elite - Open Sat, 11am to 2pmNew
$1,498,000Active3 beds 2 baths2,387 sq. ft.14 Rangeley Rdg, Winchester, MA 01890
MLS# 73538612Listed by: Compass - Open Sat, 12 to 2pmNew
$1,649,000Active4 beds 4 baths2,768 sq. ft.10 Farrow Street, Winchester, MA 01890
MLS# 73538441Listed by: Century 21 Cityside - Open Sat, 11:30am to 1pmNew
Listed by BHGRE$1,725,000Active5 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 Sat, 12 to 1:30pmNew
$2,199,000Active4 beds 4 baths3,210 sq. ft.26 N Gateway, Winchester, MA 01890
MLS# 73538052Listed by: Gibson Sotheby's International Realty - Open Sat, 11am to 12:30pmNew
$1,699,000Active4 beds 3 baths2,707 sq. ft.11 Carriage Lane, Winchester, MA 01890
MLS# 73537920Listed by: Compass - Open Sat, 11:30am to 1:30pmNew
Listed by BHGRE$1,225,000Active3 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 Sat, 11am to 12:30pmNew
$1,999,900Active4 beds 4 baths3,286 sq. ft.15 Fieldstone Dr, Winchester, MA 01890
MLS# 73537676Listed by: Barrett Sotheby's International Realty - Open Sat, 12 to 1:30pmNew
Listed by BHGRE$1,949,000Active4 beds 4 baths3,494 sq. ft.2 York Road, Winchester, MA 01890
MLS# 73537657Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - Open Sat, 11am to 12:30pmNew
$999,000Active3 beds 2 baths1,996 sq. ft.70 Grove St, Winchester, MA 01890
MLS# 73537575Listed by: William Raveis R.E. & Home Services - Open Sat, 11am to 1pmNew
$1,900,000Active4 beds 4 baths2,943 sq. ft.9 Wilson St, Winchester, MA 01890
MLS# 73537143Listed by: Compass - New
$3,199,000Active5 beds 5 baths5,406 sq. ft.10 Rangeley Road, Winchester, MA 01890
MLS# 73535697Listed by: Compass - Open Sun, 11am to 12pmNew
$1,899,000Active4 beds 3 baths3,091 sq. ft.9 Brookside Place, Winchester, MA 01890
MLS# 73534969Listed by: Compass - Open Sat, 1 to 2pmNew
$2,400,000Active5 beds 4 baths4,591 sq. ft.21 Willowdale Road, Winchester, MA 01890
MLS# 73534988Listed by: Compass - Open Sat, 11:30am to 1pmNew
Listed by BHGRE$1,330,000Active3 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 - Open Sat, 11am to 12:30pmNew
$3,799,000Active6 beds 8 baths6,000 sq. ft.29 Ginn Rd, Winchester, MA 01890
MLS# 73534577Listed by: Serhant - Open Sun, 12 to 1:30pmNew
$999,000Active5 beds 2 baths2,160 sq. ft.339-341 Washington Street, Winchester, MA 01890
MLS# 73534223Listed by: Gibson Sotheby's International Realty - Open Sun, 10 to 11am
$2,099,000Active6 beds 5 baths6,900 sq. ft.16 Glenwood Ave, Winchester, MA 01890
MLS# 73507145Listed by: Compass - Open Sat, 11am to 1pmNew
$2,199,000Active5 beds 4 baths3,474 sq. ft.211 Forest St, Winchester, MA 01890
MLS# 73532996Listed by: Stuart St James, Inc. - Open Sun, 10 to 11am
$2,099,000Active6 beds 5 baths6,900 sq. ft.16 & 16A Glenwood Ave, Winchester, MA 01890
MLS# 73507137Listed by: Compass - Open Sat, 12 to 1:30pmNew
$729,000Active2 beds 3 baths1,431 sq. ft.171 Swanton St #7, Winchester, MA 01890
MLS# 73532218Listed by: Gibson Sotheby's International Realty - Open Sat, 2:30 to 4pm
$699,900Active3 beds 4 baths1,380 sq. ft.23 Shepard Ct #U23, Winchester, MA 01890
MLS# 73530920Listed by: Fairview Partners International LLC 
$659,000Active3 beds 2 baths1,331 sq. ft.18 Bradford Road #18, Winchester, MA 01890
MLS# 73528641Listed by: Phoenix Real Estate
$1,499,000Active5 beds 5 baths3,360 sq. ft.7-9 Ridge St, Winchester, MA 01890
MLS# 73527738Listed by: The Synergy Group- Open Sat, 12 to 1:30pm
$2,529,000Active5 beds 4 baths5,230 sq. ft.78 Bacon Street, Winchester, MA 01890
MLS# 73526460Listed by: Compass 
$1,375,000Active6 beds 2 baths5,047 sq. ft.303 Washington Street, Winchester, MA 01890
MLS# 73526417Listed by: Compass- Open Sat, 12:30 to 2pm
Listed by BHGRE$1,799,000Active4 beds 3 baths3,366 sq. ft.94 Johnson Road, Winchester, MA 01890
MLS# 73525571Listed by: Better Homes and Gardens Real Estate - The Shanahan Group - Open Sat, 1:30 to 2:30pm
$2,599,000Active5 beds 4 baths5,083 sq. ft.53 Winford Way, Winchester, MA 01890
MLS# 73525195Listed by: Keller Williams Realty Boston Northwest 
$505,000Active2 beds 1 baths822 sq. ft.200 Swanton St #303, Winchester, MA 01890
MLS# 73524262Listed by: REMAX Andrew Realty Services
$1,899,000Active5 beds 3 baths3,278 sq. ft.105 Thornberry Rd, Winchester, MA 01890
MLS# 73523785Listed by: Coldwell Banker Realty - Lexington- Open Sat, 11am to 12:30pm
$1,885,000Active5 beds 4 baths3,315 sq. ft.8 Hawthorne, Winchester, MA 01890
MLS# 73522773Listed by: Coldwell Banker Realty - Lexington 
$414,500Active2 beds 1 baths1,121 sq. ft.22 Arthur St #22, Winchester, MA 01890
MLS# 73522504Listed by: MCO Realty Service, LLC
$3,600,000Active6 beds 7 baths7,400 sq. ft.2 Atherton Rd, Winchester, MA 01890
MLS# 73519229Listed by: Regatta Realty- Open Sun, 11:30am to 12:30pm
$1,225,000Active3 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
$2,675,000Active6 beds 5 baths4,540 sq. ft.47 Yale Street, Winchester, MA 01890
MLS# 73516849Listed by: Coldwell Banker Realty - Belmont
$1,150,000Active5 beds 3 baths2,186 sq. ft.63-65 Harvard Street, Winchester, MA 01890
MLS# 73515601Listed by: Keller Williams Realty Boston Northwest
$379,900Active1 beds 1 baths606 sq. ft.200 Swanton St #318, Winchester, MA 01890
MLS# 73514335Listed by: Lewis & Joyce Real Estate- Open Sat, 11am to 12pm
$3,149,000Active5 beds 6 baths6,500 sq. ft.8 Priscilla Ln, Winchester, MA 01890
MLS# 73513501Listed by: Rise Signature Homes - Open Sat, 10am to 12pm
$1,199,000Active3 beds 4 baths2,420 sq. ft.129 Washington St #129, Winchester, MA 01890
MLS# 73513572Listed by: Leading Edge Real Estate - Open Sat, 1 to 2:30pm
$2,450,000Active4 beds 4 baths4,403 sq. ft.50 Brooks Street, Winchester, MA 01890
MLS# 73510897Listed by: Compass 
$2,000,000Active6 beds 5 baths3,403 sq. ft.6 Ivy Circle, Winchester, MA 01890
MLS# 73510713Listed by: Engel & Volkers Boston
$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
$2,799,000Active6 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 Sat, 2 to 3:30pm
$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 
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
$2,195,000Active5 beds 4 baths5,006 sq. ft.276 High Street, Winchester, MA 01890
MLS# 73496396Listed by: Compass
Listed by BHGRE$3,475,000Active7 beds 6 baths7,043 sq. ft.2 Everett Ave, Winchester, MA 01890
MLS# 73488991Listed by: Better Homes and Gardens Real Estate - The Shanahan Group
$4,449,000Active5 beds 6 baths6,526 sq. ft.4 Dartmouth St, Winchester, MA 01890
MLS# 73482952Listed by: Gibson Sotheby's International Realty
$3,200,000Active6 beds 6 baths6,100 sq. ft.9 Albamont Road, Winchester, MA 01890
MLS# 73482275Listed by: Compass
$1,799,000Active3 beds 4 baths3,010 sq. ft.1 Town Way, Winchester, MA 01890
MLS# 73466233Listed by: Compass- Open Sat, 1:30 to 2:30pm
$375,000Active1 beds 1 baths606 sq. ft.200 Swanton St #228, Winchester, MA 01890
MLS# 73459781Listed by: REMAX Andrew Realty Services 
$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.