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Single Family Homes For Sale in Winchester, MA

49 Homes
 
8 Stone Ave, Winchester, MA 01890
  • $1,125,000
  • 3Bd
  • 2Ba
  • 1,684 Sq Ft
New 17 Hours
80 Nelson St, Winchester, MA 01890
  • $890,000
  • 2Bd
  • 1Ba
  • 1,489 Sq Ft
New 22 Hours
4 Harrington Rd, Winchester, MA 01890
  • $1,599,000
  • 3Bd
  • 2Ba
  • 2,966 Sq Ft
New 43 Hours
6 Aricia Ln, Winchester, MA 01890
  • $1,399,000
  • 3Bd
  • 3Ba
  • 1,975 Sq Ft
New 2 Days
30 Surrey Rd, Winchester, MA 01890
  • $1,985,000
  • 4Bd
  • 4Ba
  • 4,241 Sq Ft
New 2 Days
15 Lloyd St, Winchester, MA 01890
  • $1,399,000
  • 5Bd
  • 2Ba
  • 2,071 Sq Ft
New 6 Days
39 Forest St, Winchester, MA 01890
  • $1,299,000
  • 3Bd
  • 2Ba
  • 2,350 Sq Ft
New 6 Days
21 Amberwood Dr, Winchester, MA 01890
  • $2,049,000
  • 5Bd
  • 4Ba
  • 4,063 Sq Ft
Open SAT 11-12
63 Wedgemere Ave, Winchester, MA 01890
  • $2,399,000
  • 4Bd
  • 4Ba
  • 3,550 Sq Ft
39 Henry St, Winchester, MA 01890
  • $850,000
  • 3Bd
  • 1Ba
  • 1,313 Sq Ft
$49K
15 Vinson Cir, Winchester, MA 01890
  • $18,000,000
  • 6Bd
  • 7Ba
  • 10,000 Sq Ft
1 Plymouth Rd, Winchester, MA 01890
  • $3,299,000
  • 7Bd
  • 8Ba
  • 7,226 Sq Ft
25 Arlington St, Winchester, MA 01890
  • $1,529,000
  • 4Bd
  • 4Ba
  • 2,709 Sq Ft
26 Mayflower Rd, Winchester, MA 01890
  • $1,950,000
  • 5Bd
  • 4Ba
  • 3,371 Sq Ft
1 Overlook Way, Winchester, MA 01890
  • $1,750,000
  • 4Bd
  • 3Ba
  • 3,604 Sq Ft
Open SAT 12-2
9 Priscilla Ln, Winchester, MA 01890
  • $1,325,000
  • 4Bd
  • 2Ba
  • 1,922 Sq Ft
7 Lakeview Ter, Winchester, MA 01890
  • $2,600,000
  • 6Bd
  • 4Ba
  • 3,534 Sq Ft
30 Willowdale Rd, Winchester, MA 01890
  • $3,200,000
  • 8Bd
  • 7Ba
  • 5,750 Sq Ft
258 Cross St, Winchester, MA 01890
  • $974,900
  • 3Bd
  • 3Ba
  • 1,719 Sq Ft
37 Mayflower Rd, Winchester, MA 01890
  • $3,149,000
  • 7Bd
  • 8Ba
  • 8,540 Sq Ft
117 Highland, Winchester, MA 01890
  • $1,650,000
  • 5Bd
  • 4Ba
  • 3,722 Sq Ft
Open SAT 1-2
143 Arlington St, Winchester, MA 01890
  • $1,599,000
  • 5Bd
  • 3Ba
  • 2,944 Sq Ft
4 Dartmouth, Winchester, MA 01890
  • $4,299,000
  • 5Bd
  • 6Ba
  • 6,526 Sq Ft
465 Washington St, Winchester, MA 01890
  • $1,300,000
  • 4Bd
  • 3Ba
  • 2,666 Sq Ft
19 Hancock St, Winchester, MA 01890
  • $2,199,000
  • 4Bd
  • 4Ba
  • 3,570 Sq Ft
Open SUN 11-1
17 Churchill Rd, Winchester, MA 01890
  • $1,749,000
  • 5Bd
  • 4Ba
  • 3,508 Sq Ft
4 Churchill Rd, Winchester, MA 01890
  • $1,649,000
  • 3Bd
  • 2Ba
  • 2,421 Sq Ft
$50K
24 Richardson St, Winchester, MA 01890
  • $1,069,000
  • 4Bd
  • 3Ba
  • 2,411 Sq Ft
Open SAT 2-3
257 Cross St, Winchester, MA 01890
  • $1,050,000
  • 5Bd
  • 3Ba
  • 2,801 Sq Ft
17 Russell Rd, Winchester, MA 01890
  • $1,098,000
  • 3Bd
  • 2Ba
  • 1,657 Sq Ft
85 High St, Winchester, MA 01890
  • $1,899,000
  • 4Bd
  • 3Ba
  • 3,757 Sq Ft
Open SUN 11-1
110 Thornberry Rd, Winchester, MA 01890
  • $1,289,000
  • 3Bd
  • 3Ba
  • 2,459 Sq Ft
$40K
54 Squire Rd, Winchester, MA 01890
  • $2,399,000
  • 4Bd
  • 5Ba
  • 4,450 Sq Ft
$51K
96 Loring Ave, Winchester, MA 01890
  • $919,999
  • 4Bd
  • 2Ba
  • 2,326 Sq Ft
$30K
7 Hutchinson Rd, Winchester, MA 01890
  • $3,450,000
  • 6Bd
  • 5Ba
  • 5,735 Sq Ft
18 Ridge St, Winchester, MA 01890
  • $3,200,000
  • 5Bd
  • 6Ba
  • 5,295 Sq Ft
50 Holland St, Winchester, MA 01890
  • $1,549,000
  • 3Bd
  • 3Ba
  • 2,640 Sq Ft
11 Viking Rd, Winchester, MA 01890
  • $3,600,000
  • 7Bd
  • 8Ba
  • 7,429 Sq Ft
Open SAT 2-3
1 Town Way, Winchester, MA 01890
  • $1,749,000
  • 3Bd
  • 4Ba
  • 3,010 Sq Ft
Open SUN 11-1
15 Clark St, Winchester, MA 01890
  • $799,000
  • 3Bd
  • 2Ba
  • 1,340 Sq Ft
$50K
47 Water St, Winchester, MA 01890
  • $899,000
  • 3Bd
  • 2Ba
  • 1,356 Sq Ft
$51K
9 Plymouth Rd, Winchester, MA 01890
  • $2,250,000
  • 5Bd
  • 3Ba
  • 4,071 Sq Ft
$150K
423 Washington St, Winchester, MA 01890
  • $1,350,000
  • 4Bd
  • 3Ba
  • 2,690 Sq Ft
53 Lake St, Winchester, MA 01890
  • $1,025,000
  • 3Bd
  • 3Ba
  • 2,235 Sq Ft
$50K
18 Middlesex St, Winchester, MA 01890
  • $2,650,000
  • 4Bd
  • 5Ba
  • 5,233 Sq Ft
Open SAT 12-1
6 Ivy Cir, Winchester, MA 01890
  • $2,100,000
  • 6Bd
  • 5Ba
  • 3,403 Sq Ft
Open SAT 1-2
14 Nassau Dr, Winchester, MA 01890
  • $2,750,000
  • 6Bd
  • 7Ba
  • 6,968 Sq Ft
Open SAT 12-2
276 High St, Winchester, MA 01890
  • $2,195,000
  • 5Bd
  • 4Ba
  • 5,006 Sq Ft
$104K
9 Albamont Rd, Winchester, MA 01890
  • $3,200,000
  • 6Bd
  • 6Ba
  • 6,100 Sq Ft
$200K
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1 - 49 of 49 Houses for sale in Winchester, MA
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Winchester, MA real estate market trends

Statistics as of October 2026
$1.29M
Avg. list price
$564/Sqft
Avg. price/sqft
64
Homes for sale
2,421 Sqft
Avg. home size
40 Days
Avg. days on market
Movoto makes it easy to track market trends in Winchester, MA. Whether you’re entering the market or planning your next move, understanding these key metrics can guide smart decisions. Looking for more detailed housing market stats in Winchester, MA?
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Frequently Asked Questions about Winchester, MA

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