60+ Homes for Sale in Winchester, MA
60 results
60 homes are for sale in Winchester, MA (median list price $1,474,500), as of November 6, 2026.
$815,000
Price reduced by ↓ $75,00080 Nelson St, Winchester, MA 01890
$547/sqft · 22 days on market
$1,699,000
3 Sunset Road, Winchester, MA 01890
$621/sqft · 8 days on market
$675,000
419 Washington Street #419, Winchester, MA 01890
$443/sqft · Listed today
$649,000
421 Washington Street #421, Winchester, MA 01890
$456/sqft · Listed today
$919,000
Price reduced by ↓ $55,900258 Cross St, Winchester, MA 01890
$535/sqft · 57 days on market
What's actually happening in Winchester right now?
Forget the national headlines. Get the hyper-local, street-level data on inventory, price drops, and true market value before you make an offer.
$2,995,000
Price reduced by ↓ $205,0009 Albamont Road, Winchester, MA 01890
$491/sqft · 247 days on market
$1,499,000
Price reduced by ↓ $100,0004 Churchill Road, Winchester, MA 01890
$619/sqft · 60 days on market
$1,744,000
Price reduced by ↓ $5,0001 Town Way, Winchester, MA 01890
$579/sqft · 101 days on market
$2,149,000
Price reduced by ↓ $50,00019 Hancock Street, Winchester, MA 01890
$602/sqft · 59 days on market
$2,750,000
Price reduced by ↓ $49,00014 Nassau Drive, Winchester, MA 01890
$395/sqft · 206 days on market
$1,249,000
Price reduced by ↓ $50,000419-421 Washington St, Winchester, MA 01890
$424/sqft · 17 days on market
$1,749,000
Price reduced by ↓ $150,00085 High Street, Winchester, MA 01890
$466/sqft · 7 days on market
$1,650,000
Price reduced by ↓ $100,0001 Overlook Way, Winchester, MA 01890
$458/sqft · 44 days on market
$2,999,000
5 Forest Cir, Winchester, MA 01890
$612/sqft · 14 days on market
$1,450,000
67-69 Hemingway St, Winchester, MA 01890
$234/sqft · 14 days on market
$1,450,000
67-69 Hemingway St, Winchester, MA 01890
9 days on market
$1,549,000
50 Holland Street, Winchester, MA 01890
$587/sqft · 100 days on market
$1,350,000
36 Elmwood Ave #11, Winchester, MA 01890
$858/sqft · 51 days on market
$2,400,000
Price reduced by ↓ $200,0007 Lakeview Terrace, Winchester, MA 01890
$679/sqft · 51 days on market
$700,000
666 Main Street #217, Winchester, MA 01890
$565/sqft · 44 days on market
$664,000
Price reduced by ↓ $21,000666 Main Street #211, Winchester, MA 01890
$568/sqft · 107 days on market
$1,650,000
117 Highland, Winchester, MA 01890
$443/sqft · 58 days on market
$749,000
Price reduced by ↓ $20,00050 Middlesex Street #50, Winchester, MA 01890
$723/sqft · 122 days on market
$1,049,900
28 Olive St, Winchester, MA 01890
$589/sqft · 10 days on market
$950,000
Price reduced by ↓ $25,00083 Church Street #15, Winchester, MA 01890
$696/sqft · 212 days on market
$3,450,000
7 Hutchinson Road, Winchester, MA 01890
$602/sqft · 88 days on market
$2,195,000
Price reduced by ↓ $104,000276 High Street, Winchester, MA 01890
$438/sqft · 214 days on market
$2,299,000
Price reduced by ↓ $100,00054 Squire Road, Winchester, MA 01890
$517/sqft · 87 days on market
$1,050,000
257 Cross Street, Winchester, MA 01890
$375/sqft · 65 days on market
$2,175,000
Price reduced by ↓ $75,0009 Plymouth Rd, Winchester, MA 01890
$534/sqft · 123 days on market
Homes for sale in Winchester, MA: market at a glance
As of November 6, 2026, there are 60 homes for sale in Winchester, MA, with a median list price of $1,474,500. In August 2026, the median sale price for homes in Winchester, MA was $1,480,000, up 0.3% from a year earlier.
- Homes for sale
- 60
- Median list price
- $1,474,500
- Median sale price (August 2026)
- $1,480,000
- Median days on market (August 2026)
- 47 days
Common questions about Winchester, MA real estate
How many homes are for sale in Winchester, MA?
As of November 6, 2026, there are 60 homes for sale in Winchester, MA, including 43 single-family homes, 12 condos and 3 multi-family homes.
What is the median home price in Winchester, MA?
The median list price of homes for sale in Winchester, MA is $1,474,500. Homes that sold in August 2026 had a median sale price of $1,480,000, up 0.3% from a year earlier.
How long do homes take to sell in Winchester, MA?
Homes in Winchester, MA that sold in August 2026 had a median of 47 days on market. Homes currently for sale show a median of about 39 days on market.
What types of homes are for sale in Winchester, MA?
The homes for sale in Winchester, MA include 43 single-family homes, 12 condos and 3 multi-family homes.
Brokerage Information
JYL
Maple Park, Newton, MA, USA
(828) 275-7790
Market Area Served
Newton, Boston, Cambridge, Somerville, Medford, Needham and many more.
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