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 4, 2026.

$2,999,000

5 Forest Cir, Winchester, MA 01890

5 bds
|
4.5 ba
|
4900 sqft

$612/sqft · 12 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 · 12 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

7 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 · 98 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 · 49 days on market

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

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$2,400,000

Price reduced by

7 Lakeview Terrace, Winchester, MA 01890

6 bds
|
3 ba
|
3534 sqft

$679/sqft · 49 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 · 42 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 · 105 days on market

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

$1,650,000

117 Highland, Winchester, MA 01890

5 bds
|
3.5 ba
|
3722 sqft

$443/sqft · 56 days on market

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

$749,000

Price reduced by

50 Middlesex Street #50, Winchester, MA 01890

2 bds
|
2 ba
|
1036 sqft

$723/sqft · 120 days on market

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

$1,899,000

85 High Street, Winchester, MA 01890

4 bds
|
2.5 ba
|
3757 sqft

$505/sqft · 5 days on market

MLS® 73596915Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Catherine Albiani

$1,699,000

3 Sunset Road, Winchester, MA 01890

4 bds
|
2.5 ba
|
2736 sqft

$621/sqft · 6 days on market

MLS® 73596720Single Family Residence
Compass - Kim Covino & Co. Team

$1,499,000

Price reduced by

4 Churchill Road, Winchester, MA 01890

4 bds
|
2 ba
|
2421 sqft

$619/sqft · 58 days on market

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

$2,995,000

Price reduced by

9 Albamont Road, Winchester, MA 01890

6 bds
|
5.5 ba
|
6100 sqft

$491/sqft · 245 days on market

MLS® 73482275Single Family Residence
Compass - Kim Covino & Co. Team

$1,049,900

28 Olive St, Winchester, MA 01890

3 bds
|
2 ba
|
1783 sqft

$589/sqft · 8 days on market

MLS® 73595417Single Family Residence
The Aland Realty Group LLC - Ethan Forrest
Property at 83 Church Street #15, Winchester, MA 01890
1 / 37
Active Under Contract
Price drop

$950,000

Price reduced by

83 Church Street #15, Winchester, MA 01890

2 bds
|
1.5 ba
|
1365 sqft

$696/sqft · 210 days on market

MLS® 73497739Condominium
Better Homes and Gardens Real Estate - The Shanahan Group - Paula R. Sughrue

$2,149,000

Price reduced by

19 Hancock Street, Winchester, MA 01890

4 bds
|
3.5 ba
|
3570 sqft

$602/sqft · 57 days on market

MLS® 73572955Single Family Residence
Compass - Vita Realty Group
Property at 1 Town Way, Winchester, MA 01890
1 / 41
Active
Price drop

$1,744,000

Price reduced by

1 Town Way, Winchester, MA 01890

3 bds
|
3.5 ba
|
3010 sqft

$579/sqft · 99 days on market

MLS® 73555777Single Family Residence
Compass - Vita Realty Group

$3,450,000

7 Hutchinson Road, Winchester, MA 01890

6 bds
|
4.5 ba
|
5735 sqft

$602/sqft · 86 days on market

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

$2,195,000

Price reduced by

276 High Street, Winchester, MA 01890

5 bds
|
3.5 ba
|
5006 sqft

$438/sqft · 212 days on market

MLS® 73496396Single Family Residence
Compass - Kim Covino & Co. Team

$2,299,000

Price reduced by

54 Squire Road, Winchester, MA 01890

4 bds
|
4.5 ba
|
4450 sqft

$517/sqft · 85 days on market

MLS® 73555666Single Family Residence
The Marino Group Collection - Anthony Marino

$1,050,000

257 Cross Street, Winchester, MA 01890

5 bds
|
2.5 ba
|
2801 sqft

$375/sqft · 63 days on market

MLS® 73571418Single Family Residence
Compass - Kim Covino & Co. Team

$2,750,000

Price reduced by

14 Nassau Drive, Winchester, MA 01890

6 bds
|
6 ba
|
6968 sqft

$395/sqft · 204 days on market

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

$2,175,000

Price reduced by

9 Plymouth Rd, Winchester, MA 01890

5 bds
|
3 ba
|
4071 sqft

$534/sqft · 121 days on market

MLS® 73544924Single Family Residence
Real Broker MA, LLC - Steph Crawford Group

$1,750,000

Price reduced by

1 Overlook Way, Winchester, MA 01890

4 bds
|
2.5 ba
|
3604 sqft

$486/sqft · 42 days on market

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

$3,299,000

1 Plymouth Rd., Winchester, MA 01890

7 bds
|
7.5 ba
|
7226 sqft

$457/sqft · 34 days on market

MLS® 73585058Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group

$3,200,000

30 Willowdale Rd, Winchester, MA 01890

8 bds
|
6.5 ba
|
5750 sqft

$557/sqft · 50 days on market

MLS® 73577116Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 30 Surrey Rd, Winchester, MA 01890
1 / 42
Active Under Contract

$1,985,000

30 Surrey Rd, Winchester, MA 01890

4 bds
|
3.5 ba
|
4241 sqft

$468/sqft · 21 days on market

MLS® 73589478Single Family Residence
Barrett Sotheby's International Realty - Anne Spry

$2,650,000

18 Middlesex St, Winchester, MA 01890

4 bds
|
4.5 ba
|
5233 sqft

$506/sqft · 13 days on market

MLS® 73593868Single Family Residence
Coldwell Banker Realty - Boston - Jennifer Taves

$1,999,000

Price reduced by

21 Amberwood Dr, Winchester, MA 01890

5 bds
|
3.5 ba
|
4063 sqft

$492/sqft · 28 days on market

MLS® 73588059Single Family Residence
Compass - Gayle Winters & Co. Team

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

As of November 4, 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 $1,615,000, up 9.5% from a year earlier.

Homes for sale
60
Median list price
$1,474,500
Median sale price (August 2026)
$1,615,000
Median days on market (August 2026)
54 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 4, 2026, there are 60 homes for sale in Winchester, MA, including 43 single-family homes, 11 condos and 4 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 $1,615,000, up 9.5% 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 54 days on market. Homes currently for sale show a median of about 37 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, 11 condos and 4 multi-family homes.