Winchester
Map
Current listings (55)
For Sale
$1,799,000
1 Town Way
Winchester
3 bds | 3.5 ba | 3,010 sqft | Built 2026
MLS ID #73555777, Compass
For Sale
$3,600,000
11 Viking Road
Winchester
7 bds | 7.5 ba | 7,429 sqft | Built 2024
MLS ID #73556474, Engel & Volkers Boston
For Sale
$1,599,000
241 Ridge St
Winchester
4 bds | 2 ba | 2,480 sqft | Built 2001
MLS ID #73554036, Lillian Montalto Signature Properties
For Sale
$2,299,000
42 Wildwood Street
Winchester
7 bds | 4.5 ba | 4,930 sqft | Built 1880
MLS ID #73556122, Better Homes and Gardens Real Estate - The Shanahan Group
For Sale
$1,549,000
50 Holland Street
Winchester
3 bds | 2.5 ba | 2,640 sqft | Built 1960
MLS ID #73556633, Compass
Under Contract
$2,225,000
6 Davey Ln
Winchester
4 bds | 2 ba | 4,210 sqft | Built 1996
MLS ID #73554545, Coldwell Banker Realty - Andovers/Readings Regional
For Sale
$1,125,000
8 Oak Street
Winchester
5 bds | 2.5 ba | 2,391 sqft | Built 1870
MLS ID #73555597, The Synergy Group
For Sale
$2,300,000
14 Hillside Ave
Winchester
4 bds | 4.5 ba | 3,881 sqft | Built 1870
MLS ID #73541163, William Raveis R.E. & Home Services
For Sale
$3,299,000
1 Plymouth Rd
Winchester
7 bds | 7.5 ba | 7,226 sqft | Built 2025
MLS ID #73498293, Douglas Elliman Real Estate - The Sarkis Team
Under Contract
$1,150,000
11 Williams Cir
Winchester
4 bds | 2.5 ba | 2,392 sqft | Built 2001
MLS ID #73554139, Barrett Sotheby's International Realty
For Sale
$1,064,000
46 Clark St
Winchester
4 bds | 1.5 ba | 1,777 sqft | Built 1921
MLS ID #73547513, Keller Williams Realty Boston Northwest
For Sale
$1,899,000
79 Grove St
Winchester
5 bds | 3.5 ba | 3,210 sqft | Built 1941
MLS ID #73545952, Gibson Sotheby's International Realty
For Sale
$2,099,000
26 N Gateway
Winchester
4 bds | 3.5 ba | 3,210 sqft | Built 1959
MLS ID #73538052, Gibson Sotheby's International Realty
For Sale
$2,399,000
53 Winford Way
Winchester
5 bds | 4 ba | 5,083 sqft | Built 2025
MLS ID #73525195, Keller Williams Realty Boston Northwest
For Sale
$849,000
15 Clark St
Winchester
3 bds | 1.5 ba | 1,340 sqft | Built 1880
MLS ID #73555218, Coldwell Banker Realty - Milton
For Sale
$950,000
47 Water Street
Winchester
3 bds | 1 ba | 1,356 sqft | Built 1940
MLS ID #73549935, Leading Edge Real Estate
For Sale
Winter Pond
$2,999,000
10 Dartmouth Street
Winchester
5 bds | 2 ba | 4,028 sqft | Built 1964
MLS ID #73548103, Compass
For Sale
$1,599,000
241 Ridge St
Winchester
4 bds | 2 ba | 2,480 sqft | Built 2001
MLS ID #73546455, Lillian Montalto Signature Properties
For Sale
$3,199,000
10 Rangeley Road
Winchester
5 bds | 4.5 ba | 5,406 sqft | Built 1911
MLS ID #73535697, Compass
For Sale
$1,675,000
117 Highland Ave
Winchester
5 bds | 3.5 ba | 3,722 sqft | Built 1953
MLS ID #73538393, Better Homes and Gardens Real Estate - The Shanahan Group
For Sale
$1,175,000
38 Robinhood Rd
Winchester
3 bds | 1 ba | 1,736 sqft | Built 1956
MLS ID #73537786, Better Homes and Gardens Real Estate - The Shanahan Group
For Sale
$1,099,000
150 Cambridge Street
Winchester
3 bds | 1.5 ba | 1,711 sqft | Built 1940
MLS ID #73530959, Plunkett Properties
For Sale
$2,499,000
78 Bacon Street
Winchester
5 bds | 3.5 ba | 5,230 sqft | Built 1910
MLS ID #73526460, Compass
For Sale
$1,495,000
7 Sherman Place
Winchester
4 bds | 2.5 ba | 2,605 sqft | Built 2005
MLS ID #73514945, Compass
Under Contract
$3,099,000
10 Rangeley Road
Winchester
5 bds | 4.5 ba | 5,406 sqft | Built 1911
MLS ID #73511033, Compass
For Sale
$2,195,000
276 High Street
Winchester
5 bds | 3.5 ba | 5,006 sqft | Built 1992
MLS ID #73496396, Compass
For Sale
Winter Pond
$4,449,000
4 Dartmouth St
Winchester
5 bds | 5.5 ba | 6,526 sqft | Built 1935
MLS ID #73482952, Gibson Sotheby's International Realty
For Sale
$1,199,000
53 Lake Street
Winchester
3 bds | 2.5 ba | 2,235 sqft | Built 1864
MLS ID #73519082, Compass
For Sale
$3,179,000
37 Mayflower Road
Winchester
7 bds | 7.5 ba | 8,540 sqft | Built 2009
MLS ID #73502853, Compass
For Sale
$929,900
380 Cross Street
Winchester
4 bds | 2 ba | 1,938 sqft | Built 1939
MLS ID #73498603, Coldwell Banker Realty - Lexington
For Sale
$1,899,000
9 Brookside Place
Winchester
4 bds | 2.5 ba | 3,091 sqft | Built 1920
MLS ID #73534969, Compass
For Sale
$999,900
258 Cross Street
Winchester
4 bds | 2 ba | 1,719 sqft | Built 1860
MLS ID #73541288, Fiv Realty Co
Under Contract
$1,925,000
15 Fieldstone Dr
Winchester
4 bds | 3.5 ba | 3,286 sqft | Built 1989
MLS ID #73537676, Barrett Sotheby's International Realty
For Sale
$3,600,000
20 Amberwood Dr
Winchester
6 bds | 7 ba | 8,866 sqft | Built 2024
MLS ID #73423693, WW Real Estate LLC
Under Contract
$1,699,000
2 Olde Lyme Road
Winchester
3 bds | 3.5 ba | 2,513 sqft | Built 1960
MLS ID #73549106, Better Homes and Gardens Real Estate - The Shanahan Group
For Sale
$888,000
84 OAK STREET
Winchester
4 bds | 2 ba | 2,083 sqft | Built 1962
MLS ID #73542597, Charlesgate Realty Group LLC
Under Contract
$1,825,000
8 Hawthorne Road
Winchester
5 bds | 2 ba | 3,315 sqft | Built 1959
MLS ID #73522773, Coldwell Banker Realty - Lexington
For Sale
$1,150,000
52 Salem Street
Winchester
3 bds | 2.5 ba | 2,004 sqft | Built 1880
MLS ID #73549499, Better Homes and Gardens Real Estate - The Shanahan Group
For Sale
$1,350,000
423 Washington St
Winchester
4 bds | 3 ba | 2,690 sqft | Built 1850
MLS ID #73541775, MA Properties
For Sale
$1,899,000
16 & 16A Glenwood Ave
Winchester
6 bds | 4.5 ba | 6,900 sqft | Built 1966
MLS ID #73507137, Compass
For Sale
$2,795,000
18 Middlesex St
Winchester
4 bds | 4.5 ba | 5,233 sqft | Built 2004
MLS ID #73518621, Luxury Living Real Estate
For Sale
$3,149,000
8 Priscilla Ln
Winchester
5 bds | 5.5 ba | 6,500 sqft | Built 2025
MLS ID #73513501, Rise Signature Homes
For Sale
$2,799,000
14 Nassau Drive
Winchester
6 bds | 5 ba | 6,968 sqft | Built 2002
MLS ID #73500890, WINN Real Estate & Consulting
For Sale
$699,000
23 Shepard Ct
Winchester
3 bds | 2 ba | 1,380 sqft | Built 1890
MLS ID #73530954, Fairview Partners International LLC
For Sale
$3,350,000
2 Atherton Rd
Winchester
6 bds | 6.5 ba | 7,400 sqft | Built 2025
MLS ID #73519229, Regatta Realty
For Sale
$2,999,000
10 Dartmouth Street
Winchester
5 bds | 2 ba | 4,028 sqft | Built 1964
MLS ID #73496399, Compass
For Sale
$2,500,000
9 Plymouth Rd
Winchester
5 bds | 3 ba | 4,071 sqft | Built 1959
MLS ID #73544924, Real Broker MA, LLC
For Sale
$1,849,999
94 Johnson Road
Winchester
4 bds | 3 ba | 3,512 sqft | Built 1971
MLS ID #73497889, Compass
For Sale
$1,799,000
1 Town Way
Winchester
3 bds | 3.5 ba | 3,010 sqft | Built 2026
MLS ID #73466233, Compass
For Sale
$3,200,000
9 Albamont Road
Winchester
6 bds | 5.5 ba | 6,100 sqft | Built 2026
MLS ID #73482275, Compass
For Sale
$1,100,000
41 Cross St
Winchester
4 bds | 2 ba | 2,085 sqft | Built 1860
MLS ID #73540112, Keller Williams Realty Boston Northwest
For Sale
$2,799,000
53 Winford Way
Winchester
5 bds | 4 ba | 5,083 sqft | Built 2025
MLS ID #73481323, Keller Williams Realty Boston Northwest
For Sale
$999,000
41 Cross St
Winchester
4 bds | 2 ba | 2,085 sqft | Built 1860
MLS ID #73527486, Keller Williams Realty Boston Northwest
Under Contract
$999,000
41 Cross St
Winchester
4 bds | 2 ba | 2,085 sqft | Built 1860
MLS ID #73520534, Keller Williams Realty Boston Northwest
For Sale
$1,300,000
465 Washington St
Winchester
4 bds | 2.5 ba | 2,666 sqft | Built 2017
MLS ID #73516539, Gibson Sotheby's International Realty
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