Winchester, MA Homes For Sale
113 listings. Live MLS data, refreshed nightly. Winchester market overview
Winchester, MA
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Listings
$1,749,000
17 Churchill Rd, Winchester MA 01890
Winchester, 01890
5 bd·3.5 ba·3,508 sqft
45 days on market
Listed by Domingo Medina
$660,000
60 Lake St, Winchester MA 01890
Winchester, 01890
2 bd·1.5 ba·1,190 sqft
45 days on market
Listed by Shaundize Moosavizadeh
$2,049,000
26 N Gateway, Winchester MA 01890
Winchester, 01890
4 bd·3.5 ba·3,210 sqft
46 days on market
Listed by Pirani & Wile Group
$1,599,000
4 Churchill Road, Winchester MA 01890
Winchester, 01890
4 bd·2 ba·2,421 sqft
46 days on market
Listed by Kim Covino & Co. Team
$1,069,000
24 Richardson St, Winchester MA 01890
Winchester, 01890
4 bd·2.5 ba·2,411 sqft
50 days on market
Listed by Andersen Group Realty
$619,000
23 Shepard Ct # 23, Winchester MA 01890
Winchester, 01890
3 bd·3 ba·1,225 sqft
50 days on market
Listed by Ning Sun
$1,050,000
257 Cross Street, Winchester MA 01890
Winchester, 01890
5 bd·2.5 ba·2,801 sqft
51 days on market
Listed by Kim Covino & Co. Team
$1,098,000
17 Russell Rd, Winchester MA 01890
Winchester, 01890
3 bd·1.5 ba·1,657 sqft
64 days on market
Listed by Tsz Mui Kwan
$1,899,000
85 High St, Winchester MA 01890
Winchester, 01890
4 bd·2.5 ba·3,757 sqft
65 days on market
Listed by Catherine Albiani
$399,000
63 Shore Rd # 32, Winchester MA 01890
Winchester, 01890
65 days on market
Listed by Melanie Lentini
$3,295,000
2 Atherton Rd, Winchester MA 01890
Winchester, 01890
6 bd·6.5 ba·6,100 sqft
71 days on market
Listed by Peter Kasseris
$1,289,000
110 Thornberry Road, Winchester MA 01890
Winchester, 01890
3 bd·2.5 ba·2,459 sqft
72 days on market
Pool
Listed by Mark Kiklis
$2,399,000
54 Squire Road, Winchester MA 01890
Winchester, 01890
4 bd·4.5 ba·4,450 sqft
73 days on market
Listed by Anthony Marino
$919,999
96 Loring Ave, Winchester MA 01890
Winchester, 01890
4 bd·2 ba·2,326 sqft
73 days on market
Listed by Jeremy Smith
$3,450,000
7 Hutchinson Road, Winchester MA 01890
Winchester, 01890
6 bd·4.5 ba·5,735 sqft
74 days on market
Listed by Kim Covino & Co. Team
$3,200,000
18 Ridge St, Winchester MA 01890
Winchester, 01890
5 bd·5.5 ba·5,295 sqft
74 days on market
Listed by Gayle Winters & Co. Team
$2,999,000
5 Forest Cir, Winchester MA 01890
Winchester, 01890
5 bd·3.5 ba·4,500 sqft
78 days on market
Listed by Pirani & Wile Group
$3,600,000
11 Viking Road, Winchester MA 01890
Winchester, 01890
7 bd·7.5 ba·7,429 sqft
86 days on market
Listed by Post Advisory Group
$1,999,000
7 Wainwright Road # 113, Winchester MA 01890
Winchester, 01890
4 bd·3.5 ba·3,640 sqft
86 days on market
Listed by Kim Covino & Co. Team
$1,549,000
50 Holland Street, Winchester MA 01890
Winchester, 01890
3 bd·2.5 ba·2,640 sqft
86 days on market
Listed by Kim Covino & Co. Team
$1,749,000
1 Town Way, Winchester MA 01890
Winchester, 01890
3 bd·3.5 ba·3,010 sqft
87 days on market
Listed by Vita Realty Group
$799,000
15 Clark St, Winchester MA 01890
Winchester, 01890
3 bd·1.5 ba·1,340 sqft
88 days on market
Listed by Jeffrey Hsu
$799,000
15 Clark St # 15, Winchester MA 01890
Winchester, 01890
3 bd·1.5 ba·1,340 sqft
93 days on market
Listed by Jeffrey Hsu
$685,000
666 Main Street # 211, Winchester MA 01890
Winchester, 01890
2 bd·2 ba·1,170 sqft
93 days on market
Listed by Elizabeth Darby
Listing data provided by MLS Property Information Network via Trestle/CoreLogic. Last sample-row update: September 12, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.