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 7, 2026.

Property at 4 Churchill Road, Winchester, MA 01890
1 / 42
Active Under Contract
Price drop
Open

$1,499,000

Price reduced by

4 Churchill Road, Winchester, MA 01890

4 bds
|
2 ba
|
2421 sqft

$619/sqft · 62 days on market

MLS® 73572661Single Family Residence
Compass - Kim Covino & Co. Team

$675,000

419 Washington Street #419, Winchester, MA 01890

3 bds
|
1 ba
|
1524 sqft

$443/sqft · 2 days on market

MLS® 73599604Condominium
Coldwell Banker Realty - Lexington - The Marrocco Group

$649,000

421 Washington Street #421, Winchester, MA 01890

3 bds
|
1 ba
|
1422 sqft

$456/sqft · 2 days on market

MLS® 73599605Condominium
Coldwell Banker Realty - Lexington - The Marrocco Group

$749,000

Price reduced by

50 Middlesex Street #50, Winchester, MA 01890

2 bds
|
2 ba
|
1036 sqft

$723/sqft · 124 days on market

MLS® 73546074Condominium
Keller Williams Realty Evolution - The North Star Group

$1,650,000

117 Highland, Winchester, MA 01890

5 bds
|
3.5 ba
|
3722 sqft

$443/sqft · 60 days on market

MLS® 73573887Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Dara Singleton

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$1,599,000

9 Watson Pl, Winchester, MA 01890

3 bds
|
2.5 ba
|
1920 sqft

$833/sqft · 2 days on market

MLS® 73599800Single Family Residence
Gibson Sotheby's International Realty - Pirani & Wile Group

$1,749,000

17 Churchill Rd, Winchester, MA 01890

5 bds
|
3.5 ba
|
3508 sqft

$499/sqft · 61 days on market

MLS® 73572890Single Family Residence
Coldwell Banker Realty - Lexington - Domingo Medina

$3,295,000

Price reduced by

7 Hutchinson Road, Winchester, MA 01890

6 bds
|
4.5 ba
|
5735 sqft

$575/sqft · 90 days on market

MLS® 73561703Single Family Residence
Compass - Kim Covino & Co. Team

$999,000

Price reduced by

53 Lake Street, Winchester, MA 01890

3 bds
|
2.5 ba
|
2235 sqft

$447/sqft · 178 days on market

MLS® 73519082Single Family Residence
Compass - Kim Covino & Co. Team
Property at 47 Water Street, Winchester, MA 01890
1 / 30
Active Under Contract
Price drop

$899,000

Price reduced by

47 Water Street, Winchester, MA 01890

3 bds
|
1.5 ba
|
1356 sqft

$663/sqft · 116 days on market

MLS® 73549935Single Family Residence
Leading Edge Real Estate - The Mary Scimemi Team

$1,449,000

15 Madison Ave W, Winchester, MA 01890

4 bds
|
2.5 ba
|
2855 sqft

$508/sqft · 2 days on market

MLS® 73599772Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty
Property at 80 Nelson St, Winchester, MA 01890
1 / 34
Active
Price drop
Open

$815,000

Price reduced by

80 Nelson St, Winchester, MA 01890

2 bds
|
1 ba
|
1489 sqft

$547/sqft · 24 days on market

MLS® 73591108Single Family Residence
Compass - Kim Covino & Co. Team
Property at 3 Sunset Road, Winchester, MA 01890
1 / 42
Active Under Contract

$1,699,000

3 Sunset Road, Winchester, MA 01890

4 bds
|
2.5 ba
|
2736 sqft

$621/sqft · 10 days on market

MLS® 73596720Single Family Residence
Compass - Kim Covino & Co. Team
Property at 258 Cross St, Winchester, MA 01890
1 / 34
Active
Price drop
Open

$919,000

Price reduced by

258 Cross St, Winchester, MA 01890

4 bds
|
2.5 ba
|
1719 sqft

$535/sqft · 59 days on market

MLS® 73575764Single Family Residence
Fiv Realty Co - Justin Blankenship
Property at 9 Albamont Road, Winchester, MA 01890
1 / 41
Active
Price drop
Open

$2,995,000

Price reduced by

9 Albamont Road, Winchester, MA 01890

6 bds
|
5.5 ba
|
6100 sqft

$491/sqft · 249 days on market

MLS® 73482275Single Family Residence
Compass - Kim Covino & Co. Team
Property at 1 Town Way, Winchester, MA 01890
1 / 41
Active
Price drop
Open

$1,744,000

Price reduced by

1 Town Way, Winchester, MA 01890

3 bds
|
3.5 ba
|
3010 sqft

$579/sqft · 103 days on market

MLS® 73555777Single Family Residence
Compass - Vita Realty Group
Property at 19 Hancock Street, Winchester, MA 01890
1 / 40
Active
Price drop
Open

$2,149,000

Price reduced by

19 Hancock Street, Winchester, MA 01890

4 bds
|
3.5 ba
|
3570 sqft

$602/sqft · 61 days on market

MLS® 73572955Single Family Residence
Compass - Vita Realty Group

$2,750,000

Price reduced by

14 Nassau Drive, Winchester, MA 01890

6 bds
|
6 ba
|
6968 sqft

$395/sqft · 208 days on market

MLS® 73500890Single Family Residence
WINN Real Estate & Consulting - Weidong Li

$1,249,000

Price reduced by

419-421 Washington St, Winchester, MA 01890

6 bds
|
2 ba
|
2946 sqft

$424/sqft · 19 days on market

MLS® 73592723Multi Family
Coldwell Banker Realty - Lexington - The Marrocco Group
Property at 85 High Street, Winchester, MA 01890
1 / 36
Active
Price drop
Open

$1,749,000

Price reduced by

85 High Street, Winchester, MA 01890

4 bds
|
2.5 ba
|
3757 sqft

$466/sqft · 9 days on market

MLS® 73596915Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Catherine Albiani
Property at 1 Overlook Way, Winchester, MA 01890
1 / 40
Active
Price drop
Open

$1,650,000

Price reduced by

1 Overlook Way, Winchester, MA 01890

4 bds
|
2.5 ba
|
3604 sqft

$458/sqft · 46 days on market

MLS® 73581571Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Lynne Russo

$2,999,000

5 Forest Cir, Winchester, MA 01890

5 bds
|
4.5 ba
|
4900 sqft

$612/sqft · 16 days on market

MLS® 73594545Single Family Residence
Gibson Sotheby's International Realty - Pirani & Wile Group

$1,450,000

67-69 Hemingway St, Winchester, MA 01890

8 bds
|
5 ba
|
6200 sqft

$234/sqft · 16 days on market

MLS® 73594547Multi Family
Gibson Sotheby's International Realty - Pirani & Wile Group

$1,450,000

67-69 Hemingway St, Winchester, MA 01890

0 bds
|
0 ba
|
-- sqft

11 days on market

MLS® 73595844Residential
Gibson Sotheby's International Realty - Pirani & Wile Group

$1,549,000

50 Holland Street, Winchester, MA 01890

3 bds
|
2.5 ba
|
2640 sqft

$587/sqft · 102 days on market

MLS® 73556633Single Family Residence
Compass - Kim Covino & Co. Team

$1,350,000

36 Elmwood Ave #11, Winchester, MA 01890

2 bds
|
2.5 ba
|
1573 sqft

$858/sqft · 53 days on market

MLS® 73578288Condominium
Keller Williams Realty Boston-Metro | Back Bay - The Rasner Group

$2,400,000

Price reduced by

7 Lakeview Terrace, Winchester, MA 01890

6 bds
|
3 ba
|
3534 sqft

$679/sqft · 53 days on market

MLS® 73578443Single Family Residence
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby

$700,000

666 Main Street #217, Winchester, MA 01890

2 bds
|
2 ba
|
1240 sqft

$565/sqft · 46 days on market

MLS® 73581469Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby

$664,000

Price reduced by

666 Main Street #211, Winchester, MA 01890

2 bds
|
2 ba
|
1170 sqft

$568/sqft · 109 days on market

MLS® 73553517Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby

$1,049,900

28 Olive St, Winchester, MA 01890

3 bds
|
2 ba
|
1783 sqft

$589/sqft · 12 days on market

MLS® 73595417Single Family Residence
The Aland Realty Group LLC - Ethan Forrest

Homes for sale in Winchester, MA: market at a glance

As of November 7, 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
Median sale price, Sep 2025 – Aug 2026

Common questions about Winchester, MA real estate

How many homes are for sale in Winchester, MA?

As of November 7, 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.