Winchester, MA Homes For Sale
113 listings. Live MLS data, refreshed nightly. Winchester market overview
Winchester, MA
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Listings
$899,000
47 Water Street, Winchester MA 01890
Winchester, 01890
3 bd·1.5 ba·1,356 sqft
100 days on market
Listed by The Mary Scimemi Team
$600,000
247 Washington St # 11, Winchester MA 01890
Winchester, 01890
3 bd·2.5 ba·1,494 sqft
100 days on market
Listed by Heejeong Joo
$288,750
200 Swanton # L8, Winchester MA 01890
Winchester, 01890
1 bd·1 ba·388 sqft
104 days on market
Listed by Stephen DeConto
$1,870,000
79 Grove St, Winchester MA 01890
Winchester, 01890
5 bd·3.5 ba·3,210 sqft
108 days on market
Listed by Pirani & Wile Group
$769,000
50 Middlesex Street # 50, Winchester MA 01890
Winchester, 01890
2 bd·2 ba·1,036 sqft
108 days on market
Listed by The North Star Group
$2,250,000
9 Plymouth Rd, Winchester MA 01890
Winchester, 01890
5 bd·3 ba·4,071 sqft
109 days on market
Listed by Steph Crawford Group
$649,900
666 Main Street # 315, Winchester MA 01890
Winchester, 01890
2 bd·2 ba·1,025 sqft
114 days on market
Waterfront
Listed by Kim Covino & Co. Team
$799,000
84 Oak Street, Winchester MA 01890
Winchester, 01890
4 bd·2 ba·2,083 sqft
119 days on market
Listed by John E. Magazzu
$1,350,000
423 Washington St, Winchester MA 01890
Winchester, 01890
4 bd·3 ba·2,690 sqft
120 days on market
Listed by Danielle Fleming
$2,380,000
14 Hillside Ave, Winchester MA 01890
Winchester, 01890
4 bd·4.5 ba·3,881 sqft
121 days on market
Listed by Rebecca Huang
$999,900
258 Cross Street, Winchester MA 01890
Winchester, 01890
4 bd·2 ba·1,719 sqft
121 days on market
Listed by Justin Blankenship
$1,100,000
41 Cross St, Winchester MA 01890
Winchester, 01890
4 bd·2 ba·2,085 sqft
122 days on market
Listed by Andersen Group Realty
$374,900
200 Swanton St # 412, Winchester MA 01890
Winchester, 01890
1 bd·1 ba·606 sqft
126 days on market
Listed by Wei Wang
$2,199,000
26 N Gateway, Winchester MA 01890
Winchester, 01890
4 bd·3.5 ba·3,210 sqft
127 days on market
Listed by Pirani & Wile Group
$1,675,000
117 Highland Ave, Winchester MA 01890
Winchester, 01890
5 bd·3.5 ba·3,722 sqft
127 days on market
Pool
Listed by Dara Singleton
$3,199,000
10 Rangeley Road, Winchester MA 01890
Winchester, 01890
5 bd·4.5 ba·5,406 sqft
131 days on market
Listed by Karima Alami
$1,899,000
9 Brookside Place, Winchester MA 01890
Winchester, 01890
4 bd·2.5 ba·3,091 sqft
134 days on market
Listed by Kim Covino & Co. Team
$1,330,000
7 Wainwright Road # 47, Winchester MA 01890
Winchester, 01890
3 bd·3 ba·2,145 sqft
134 days on market
Listed by Felicity F. Tuttle
$699,900
23 Shepard Ct # U23, Winchester MA 01890
Winchester, 01890
3 bd·3 ba·1,380 sqft
140 days on market
Listed by Nancy Zhang Zhenning
$699,000
23 Shepard Ct # U23, Winchester MA 01890
Winchester, 01890
3 bd·3 ba·1,380 sqft
140 days on market
Listed by Nancy Zhang Zhenning
$499,999
200 Swanton St # 303, Winchester MA 01890
Winchester, 01890
2 bd·1 ba·822 sqft
150 days on market
Listed by Joan Powell
$3,600,000
2 Atherton Rd, Winchester MA 01890
Winchester, 01890
6 bd·6.5 ba·7,400 sqft
162 days on market
Listed by Brooke Zarbano
$1,025,000
53 Lake Street, Winchester MA 01890
Winchester, 01890
3 bd·2.5 ba·2,235 sqft
162 days on market
Listed by Kim Covino & Co. Team
$2,650,000
18 Middlesex St, Winchester MA 01890
Winchester, 01890
4 bd·4.5 ba·5,233 sqft
163 days on market
Pool
Listed by Tina Natale
Listing data provided by MLS Property Information Network via Trestle/CoreLogic. Last sample-row update: September 19, 2026. Information herein deemed reliable but not guaranteed. Equal Housing Opportunity.