Winchester, MA - single-family homes for sale

38 of 38 results displayed

Open Sat, 11am to 12pmNew
$1,099,000Active
4 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
$1,599,000Active
4 beds 4 baths2,480 sq. ft.
241 Ridge St, Winchester, MA 01890
MLS# 73546455Listed by: Lillian Montalto Signature Properties
Open Sat, 12 to 1:30pmNew
$1,899,000Active
5 beds 4 baths3,210 sq. ft.
79 Grove St, Winchester, MA 01890
MLS# 73545952Listed by: Gibson Sotheby's International Realty
Open Sat, 1 to 2:30pmNew
$1,300,000Active
3 beds 2 baths2,006 sq. ft.
3 Chesterford Terrace, Winchester, MA 01890
MLS# 73545054Listed by: Compass
Open Sun, 12 to 2pmNew
$2,500,000Active
5 beds 3 baths4,071 sq. ft.
9 Plymouth Rd, Winchester, MA 01890
MLS# 73544924Listed by: Real Broker MA, LLC
$900,000Active
4 beds 2 baths2,083 sq. ft.
84 Oak Street, Winchester, MA 01890
MLS# 73542597Listed by: Charlesgate Realty Group LLC
$1,350,000Active
4 beds 3 baths2,690 sq. ft.
423 Washington St, Winchester, MA 01890
MLS# 73541775Listed by: MA Properties
Open Sat, 12:30 to 2pm
$999,900Active
4 beds 2 baths1,719 sq. ft.
258 Cross Street, Winchester, MA 01890
MLS# 73541288Listed by: Fiv Realty Co
Open Sun, 11am to 12:30pm
$2,380,000Active
4 beds 5 baths3,881 sq. ft.
14 Hillside Ave, Winchester, MA 01890
MLS# 73541163Listed by: William Raveis R.E. & Home Services
$1,099,000Active
3 beds 2 baths1,711 sq. ft.
150 Cambridge Street, Winchester, MA 01890
MLS# 73530959Listed by: Plunkett Properties
Open Sun, 2 to 3:30pm
$1,725,000Active
5 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, 11am to 12pm
$2,149,000Active
4 beds 4 baths3,210 sq. ft.
26 N Gateway, Winchester, MA 01890
MLS# 73538052Listed by: Gibson Sotheby's International Realty
Open Sat, 12 to 1:30pm
$1,225,000Active
3 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, 12 to 1:30pm
$1,999,900Active
4 beds 4 baths3,286 sq. ft.
15 Fieldstone Dr, Winchester, MA 01890
MLS# 73537676Listed by: Barrett Sotheby's International Realty
$3,199,000Active
5 beds 5 baths5,406 sq. ft.
10 Rangeley Road, Winchester, MA 01890
MLS# 73535697Listed by: Compass
Open Sun, 12 to 1pm
$1,899,000Active
4 beds 3 baths3,091 sq. ft.
9 Brookside Place, Winchester, MA 01890
MLS# 73534969Listed by: Compass
$3,799,000Active
6 beds 8 baths6,000 sq. ft.
29 Ginn Rd, Winchester, MA 01890
MLS# 73534577Listed by: Serhant
Open Sun, 11am to 12:30pm
$1,999,000Active
6 beds 5 baths6,900 sq. ft.
16 & 16A Glenwood Ave, Winchester, MA 01890
MLS# 73507137Listed by: Compass
$2,529,000Active
5 beds 4 baths5,230 sq. ft.
78 Bacon Street, Winchester, MA 01890
MLS# 73526460Listed by: Compass
$1,799,000Active
4 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, 12:30 to 1:30pm
$2,399,000Active
5 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
$1,825,000Active
5 beds 4 baths3,315 sq. ft.
8 Hawthorne Road, Winchester, MA 01890
MLS# 73522773Listed by: Coldwell Banker Realty - Lexington
Open Sat, 12:30 to 2pm
$3,350,000Active
6 beds 7 baths7,400 sq. ft.
2 Atherton Rd, Winchester, MA 01890
MLS# 73519229Listed by: Regatta Realty
Open Sun, 1:30 to 2:30pm
$1,199,000Active
3 beds 3 baths2,235 sq. ft.
53 Lake Street, Winchester, MA 01890
MLS# 73519082Listed by: Compass
$2,795,000Active
4 beds 5 baths5,233 sq. ft.
18 Middlesex St, Winchester, MA 01890
MLS# 73518621Listed by: Luxury Living Real Estate
$3,149,000Active
5 beds 6 baths6,500 sq. ft.
8 Priscilla Ln, Winchester, MA 01890
MLS# 73513501Listed by: Rise Signature Homes
$2,450,000Active
4 beds 4 baths4,403 sq. ft.
50 Brooks Street, Winchester, MA 01890
MLS# 73510897Listed by: Compass
$3,379,000Active
7 beds 8 baths8,540 sq. ft.
37 Mayflower Road, Winchester, MA 01890
MLS# 73502853Listed by: Compass
$2,799,000Active
6 beds 7 baths6,968 sq. ft.
14 Nassau Drive, Winchester, MA 01890
MLS# 73500890Listed by: WINN Real Estate & Consulting
Open Sat, 11am to 12:30pm
$929,900Active
4 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
$3,299,000Active
7 beds 8 baths7,226 sq. ft.
1 Plymouth Rd, Winchester, MA 01890
MLS# 73498293Listed by: Douglas Elliman Real Estate - The Sarkis Team
$2,195,000Active
5 beds 4 baths5,006 sq. ft.
276 High Street, Winchester, MA 01890
MLS# 73496396Listed by: Compass
$3,200,000Active
6 beds 6 baths6,100 sq. ft.
9 Albamont Road, Winchester, MA 01890
MLS# 73482275Listed by: Compass
$1,799,000Active
3 beds 4 baths3,010 sq. ft.
1 Town Way, Winchester, MA 01890
MLS# 73466233Listed by: Compass
Open Sun, 12:30 to 2pm
$3,600,000Active
6 beds 7 baths8,866 sq. ft.
20 Amberwood Dr, Winchester, MA 01890
MLS# 73423693Listed by: WW Real Estate LLC
$949,900Active
4 beds 3 baths1,880 sq. ft.
116 Forest St, Winchester, MA 01890
MLS# 73179157Listed by: Berkshire Hathaway HomeServices Commonwealth Real Estate
$2,799,000Active
5 beds 6 baths6,067 sq. ft.
10 North Gateway, Winchester, MA 01890
MLS# 73158946Listed by: Compass
$2,799,000Active
5 beds 5 baths5,000 sq. ft.
1 Alice Lane, Winchester, MA 01890
MLS# 73107072Listed by: Compass

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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.

Terms of use Accessibility DMCA notice Fraud alert Privacy policy Fair housing Do not sell info NY reasonable accommodation Submit agent or broker complaint

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.