139 High St, Winchester, MA 01890BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP, Katie Tully$945,0003 bds2 ba1,302 sqft - SoldSold 02/12/26Save this home
16 Ridge St, Winchester, MA 01890COMPASS, Kim Covino & Co. Team$1.09M3 bds3 ba1,844 sqft - SoldSave this home
112 Wendell St, Winchester, MA 01890GIBSON SOTHEBY'S INTERNATIONAL REALTY, Steve McKenna & The Home Advantage Team$1.34M4 bds3 ba2,854 sqft - SoldSold 02/04/26Save this home
7 Appalachian Rd, Winchester, MA 01890BARRETT SOTHEBY'S INTERNATIONAL REALTY, Anne Spry$2.15M4 bds5 ba3,263 sqft - SoldSold 02/02/26Save this home
200 Swanton St APT 630, Winchester, MA 01890LYV REALTY, Angela Hirtle$340,0001 bd1 ba613 sqft - SoldSold 02/02/26Save this home
149 Horn Pond Brook Rd, Winchester, MA 01890REDFIN CORP., Nancy Ciampa McLaughlin$1.64M5 bds2 ba2,331 sqft - SoldSold 01/30/26Save this home
46-48 SW Anton St, Winchester, MA 01890COMPASS, Leeman & Gately$1.29M6 bds4 ba3,233 sqft - SoldSold 01/29/26Save this home
46 Church St, Winchester, MA 01890BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP, Joan Francis Sullivan$1.97M4 bds4 ba3,475 sqft - SoldSold 01/27/26Save this home
41 Squire Rd, Winchester, MA 01890CHARLESGATE REALTY GROUP, LLC, William Cordts$955,2254 bds2 ba2,162 sqft - SoldSave this home
32 Oak St, Winchester, MA 01890KELLER WILLIAMS REALTY-MERRIMACK, Julia and Joanne (Guozhen) Team$1.38M4 bds3 ba2,652 sqft - SoldSold 01/23/26Save this home
5 Wood Ln, Winchester, MA 01890COMPASS, Kim Covino & Co. Team$2.00M3 bds3 ba2,443 sqft - SoldSold 01/20/26Save this home
19 Gershon Way #1, Winchester, MA 01890COMPASS, Vita Realty Group$2.18M3 bds3 ba3,953 sqft - SoldSold 01/16/26Save this home
7-7-7A Brooks St, Winchester, MA 01890BARRETT SOTHEBY'S INTERNATIONAL REALTY, Anne Spry$1.85M6 bds4 ba4,122 sqft - SoldSave this home
189 High St, Winchester, MA 01890BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP, Paula R. Sughrue$1.19M4 bds3 ba2,126 sqft - SoldSold 01/13/26Save this home
7 Wainwright Rd Unit 118, Winchester, MA 01890BERKSHIRE HATHAWAY HOMESERVICES COMMONWEALTH REAL ESTATE, Giordana Fioravanti Smith$1.50M3 bds4 ba3,807 sqft - SoldSold 01/10/26Save this home
8 Felsdale Close, Winchester, MA 01890BARRETT SOTHEBY'S INTERNATIONAL REALTY, Anne Spry$1.93M4 bds3 ba3,658 sqft - SoldSold 01/09/26Save this home
29 Shepard Ct, Winchester, MA 01890GIBSON SOTHEBY'S INTERNATIONAL REALTY, Pirani & Wile Group$2.45M6 bds5 ba4,594 sqft - SoldSold 01/09/26Save this home
53 Bacon St, Winchester, MA 01890LEADING EDGE REAL ESTATE, Taleen Chiofaro$1.39M3 bds3 ba2,865 sqft - SoldSold 01/09/26Save this home
104 Church St, Winchester, MA 01890COMPASS, Kim Covino & Co. Team$1.26M4 bds2 ba2,696 sqft - SoldSold 01/07/26Save this home
5 Bacon St, Winchester, MA 01890BARRETT SOTHEBY'S INTERNATIONAL REALTY, Anne Spry$2.09M6 bds4 ba4,385 sqft - SoldSold 01/06/26Save this home
571 Washington St, Winchester, MA 01890KELLER WILLIAMS REALTY, Wilson Group$900,0003 bds1 ba1,425 sqft - SoldSold 01/05/26Save this home
82 Hillcrest Pkwy, Winchester, MA 01890BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP, Paula R. Sughrue$1.56M3 bds3 ba1,882 sqft - SoldSold 01/05/26Save this home
4 Wyman Ct #4, Winchester, MA 01890COLDWELL BANKER REALTY - LEXINGTON, The Marrocco Group$1.40M4 bds5 ba2,500 sqft - SoldSold 01/05/26Save this home
6 Wyman Ct #6, Winchester, MA 01890COLDWELL BANKER REALTY - LEXINGTON, The Marrocco Group$1.38M3 bds5 ba2,722 sqft - SoldSold 01/05/26Save this home
1 Copley St, Winchester, MA 01890BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP, Nannette Shanahan$1.87M7 bds3 ba2,998 sqft - SoldSold 12/30/25Save this home
7 Thornberry Rd, Winchester, MA 01890COMPASS, Kim Covino & Co. Team$1.31M5 bds2 ba3,033 sqft - SoldSold 12/24/25Save this home
209 Washington St #209, Winchester, MA 01890COMPASS, Kim Covino & Co. Team$1.50M5 bds4 ba3,141 sqft - SoldSold 12/24/25Save this home
446 Highland Ave, Winchester, MA 01890KELLER WILLIAMS REALTY BOSTON NORTHWEST, Andersen Group Realty$940,0002 bds2 ba2,033 sqft - SoldSold 12/23/25Save this home
9 Norfolk Rd, Winchester, MA 01890CITYLIGHT HOMES LLC, Jody Fricia Geany$2.40M6 bds4 ba4,320 sqft - SoldSold 12/23/25Save this home
12 Canterbury Rd, Winchester, MA 01890BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP, Paula R. Sughrue$1.33M3 bds3 ba1,942 sqft - SoldSold 12/22/25Save this home
26 N Gtwy, Winchester, MA 01890HOMES UNLIMITED, Robert Dell$1.07M2 bds1 ba1,666 sqft - SoldSold 12/22/25Save this home
19 Laurel Hill Ln, Winchester, MA 01890GIBSON SOTHEBY'S INTERNATIONAL REALTY, Mark Donnellan$2.40M5 bds5 ba3,700 sqft - SoldSold 12/18/25Save this home
30 Prospect St, Winchester, MA 01890COMPASS, Karima Alami$2.45M4 bds3 ba2,519 sqft - SoldSold 12/16/25Save this home
32 Woodside Rd, Winchester, MA 01890COMPASS, Kim Covino & Co. Team$1.55M3 bds3 ba2,587 sqft - SoldSold 12/15/25Save this home
50 Lincoln St, Winchester, MA 01890BETTER HOMES AND GARDENS REAL ESTATE - THE SHANAHAN GROUP, Lynne Russo$1.15M4 bds2 ba2,004 sqft - SoldSold 12/12/25Save this home
5 Azalea Rd, Winchester, MA 01890THE MARINO GROUP COLLECTION, Anthony Marino$2.00M5 bds4 ba6,232 sqft - SoldSave this home
14 Grant Rd, Winchester, MA 01890COLDWELL BANKER REALTY - LEXINGTON, The Marrocco Group$2.25M6 bds5 ba4,200 sqft - SoldSold 12/11/25Save this home
19 Glengarry Rd, Winchester, MA 01890COMPASS, Kim Covino & Co. Team$1.83M6 bds4 ba3,521 sqft - SoldSold 12/08/25Save this home
10 Sheffield Rd, Winchester, MA 01890KELLER WILLIAMS REALTY BOSTON NORTHWEST, Andersen Group Realty$2.63M7 bds6 ba5,864 sqft - SoldSold 12/08/25Save this home