40+ Houses for Sale in Winchester, MA

44 results

44 single-family homes are for sale in Winchester, MA (median list price $1,942,000), 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

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

$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

$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

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.

$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 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 · 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
Open

$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
Property at 24 Richardson St, Winchester, MA 01890
1 / 40
Active
Price drop
Open

$1,049,000

Price reduced by

24 Richardson St, Winchester, MA 01890

4 bds
|
2.5 ba
|
2411 sqft

$435/sqft · 62 days on market

MLS® 73571480Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty
Property at 39 Henry Street, Winchester, MA 01890
1 / 22
Active
Price drop
Open

$850,000

Price reduced by

39 Henry Street, Winchester, MA 01890

3 bds
|
1 ba
|
1313 sqft

$647/sqft · 34 days on market

MLS® 73585414Single Family Residence
Coldwell Banker Realty - Belmont - Kelly Batti

$1,250,000

Price reduced by

465 Washington Street, Winchester, MA 01890

4 bds
|
2.5 ba
|
2666 sqft

$469/sqft · 55 days on market

MLS® 73574928Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group

$3,799,000

15 Foxcroft Rd, Winchester, MA 01890

8 bds
|
5 ba
|
7081 sqft

$537/sqft · 14 days on market

MLS® 73593484Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Karen S. Garrett

$2,950,000

18 Surrey Road, Winchester, MA 01890

6 bds
|
4 ba
|
4752 sqft

$621/sqft · 16 days on market

MLS® 73592433Single Family Residence
Century 21 Property Central Inc. - Mary Kelly

$1,025,000

Price reduced by

53 Lake Street, Winchester, MA 01890

3 bds
|
2.5 ba
|
2235 sqft

$459/sqft · 174 days on market

MLS® 73519082Single Family Residence
Compass - Kim Covino & Co. Team

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

As of November 4, 2026, there are 44 single-family homes for sale in Winchester, MA, with a median list price of $1,942,000. In August 2026, the median sale price for homes in Winchester, MA (all home types) was $1,615,000, up 9.5% from a year earlier.

Houses for sale
44
Median list price
$1,942,000
Median sale price (August 2026, all home types)
$1,615,000
Median days on market (August 2026, all home types)
54 days
Median sale price, Sep 2025 – Aug 2026

Common questions about Winchester, MA real estate

How many single-family homes are for sale in Winchester, MA?

As of November 4, 2026, there are 44 single-family homes for sale in Winchester, MA.

What is the median single-family home price in Winchester, MA?

The median list price of single-family homes for sale in Winchester, MA is $1,942,000. Homes (all home types) 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 (all home types) in Winchester, MA that sold in August 2026 had a median of 54 days on market. Single-family homes currently for sale show a median of about 37 days on market.