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40+ Houses for Sale in Winchester, MA

47 results

Property at 9 Plymouth Rd, Winchester, MA 01890
1 / 37
Active
Price

$2,175,000

9 Plymouth Rd, Winchester, MA 01890

5 bds
|
3 ba
|
4071 sqft
MLS® 73544924Single Family Residence
Real Broker MA, LLC - Steph Crawford Group
Property at 28 Olive St, Winchester, MA 01890
1 / 8
Active
New
Open

$1,049,900

28 Olive St, Winchester, MA 01890

3 bds
|
2 ba
|
1783 sqft
MLS® 73595417Single Family Residence
The Aland Realty Group LLC - Ethan Forrest
Property at 5 Forest Cir, Winchester, MA 01890
1 / 10
Active

$2,999,000

5 Forest Cir, Winchester, MA 01890

5 bds
|
4.5 ba
|
4900 sqft
MLS® 73594545Single Family Residence
Gibson Sotheby's International Realty - Pirani & Wile Group
Property at 24 Richardson St, Winchester, MA 01890
1 / 40
Active
Price
Open

$1,049,000

24 Richardson St, Winchester, MA 01890

4 bds
|
2.5 ba
|
2411 sqft
MLS® 73571480Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty
Property at 39 Henry Street, Winchester, MA 01890
1 / 22
Active
Price

$850,000

39 Henry Street, Winchester, MA 01890

3 bds
|
1 ba
|
1313 sqft
MLS® 73585414Single Family Residence
Coldwell Banker Realty - Belmont - Kelly Batti

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Property at 18 Middlesex St, Winchester, MA 01890
1 / 32
Active

$2,650,000

18 Middlesex St, Winchester, MA 01890

4 bds
|
4.5 ba
|
5233 sqft
MLS® 73593868Single Family Residence
Coldwell Banker Realty - Boston - Jennifer Taves
Property at 21 Amberwood Dr, Winchester, MA 01890
1 / 42
Active
Price

$1,999,000

21 Amberwood Dr, Winchester, MA 01890

5 bds
|
3.5 ba
|
4063 sqft
MLS® 73588059Single Family Residence
Compass - Gayle Winters & Co. Team
Property at 465 Washington Street, Winchester, MA 01890
1 / 28
Active
Price

$1,250,000

465 Washington Street, Winchester, MA 01890

4 bds
|
2.5 ba
|
2666 sqft
MLS® 73574928Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 15 Foxcroft Rd, Winchester, MA 01890
1 / 40
Active

$3,799,000

15 Foxcroft Rd, Winchester, MA 01890

8 bds
|
5 ba
|
7081 sqft
MLS® 73593484Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Karen S. Garrett
Property at 7 Lakeview Terrace, Winchester, MA 01890
1 / 42
Active
Price

$2,400,000

7 Lakeview Terrace, Winchester, MA 01890

6 bds
|
3 ba
|
3534 sqft
MLS® 73578443Single Family Residence
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 9 Albamont Road, Winchester, MA 01890
1 / 42
Active
Price

$3,200,000

9 Albamont Road, Winchester, MA 01890

6 bds
|
5.5 ba
|
6100 sqft
MLS® 73482275Single Family Residence
Compass - Kim Covino & Co. Team
Property at 25 Arlington St, Winchester, MA 01890
1 / 32
Active Under Contract

$1,529,000

25 Arlington St, Winchester, MA 01890

4 bds
|
3.5 ba
|
2709 sqft
MLS® 73584817Single Family Residence
Coldwell Banker Realty - Lexington - Domingo Medina
Property at 18 Surrey Road, Winchester, MA 01890
1 / 41
Active

$2,950,000

18 Surrey Road, Winchester, MA 01890

6 bds
|
4 ba
|
4752 sqft
MLS® 73592433Single Family Residence
Century 21 Property Central Inc. - Mary Kelly
Property at 53 Lake Street, Winchester, MA 01890
1 / 42
Active
Price

$1,025,000

53 Lake Street, Winchester, MA 01890

3 bds
|
2.5 ba
|
2235 sqft
MLS® 73519082Single Family Residence
Compass - Kim Covino & Co. Team
Property at 8 Stone Ave, Winchester, MA 01890
1 / 22
Active Under Contract

$1,125,000

8 Stone Ave, Winchester, MA 01890

3 bds
|
1.5 ba
|
1684 sqft
MLS® 73591400Single Family Residence
Barrett Sotheby's International Realty - Lesley Smith
Property at 15 Lloyd Street, Winchester, MA 01890
1 / 41
Active Under Contract

$1,399,000

15 Lloyd Street, Winchester, MA 01890

5 bds
|
1.5 ba
|
2071 sqft
MLS® 73588977Single Family Residence
Compass - Kim Covino & Co. Team
Property at 4 Churchill Road, Winchester, MA 01890
1 / 42
Active
Price

$1,599,000

4 Churchill Road, Winchester, MA 01890

4 bds
|
2 ba
|
2421 sqft
MLS® 73572661Single Family Residence
Compass - Kim Covino & Co. Team
Property at 30 Surrey Rd, Winchester, MA 01890
1 / 42
Active

$1,985,000

30 Surrey Rd, Winchester, MA 01890

4 bds
|
3.5 ba
|
4241 sqft
MLS® 73589478Single Family Residence
Barrett Sotheby's International Realty - Anne Spry
Property at 110 Thornberry Road, Winchester, MA 01890
1 / 30
Active Under Contract
Price

$1,289,000

110 Thornberry Road, Winchester, MA 01890

3 bds
|
2.5 ba
|
2459 sqft
MLS® 73562273Single Family Residence
Kiklis Real Estate, LLC - Mark Kiklis
Property at 80 Nelson St, Winchester, MA 01890
1 / 34
Active

$890,000

80 Nelson St, Winchester, MA 01890

2 bds
|
1 ba
|
1489 sqft
MLS® 73591108Single Family Residence
Compass - Kim Covino & Co. Team
Property at 39 Forest St, Winchester, MA 01890
1 / 38
Active Under Contract

$1,299,000

39 Forest St, Winchester, MA 01890

3 bds
|
2 ba
|
2350 sqft
MLS® 73588863Single Family Residence
Berkshire Hathaway HomeServices Commonwealth Real Estate - Danielle Storella
Property at 1 Overlook Way, Winchester, MA 01890
1 / 40
Active
Price

$1,750,000

1 Overlook Way, Winchester, MA 01890

4 bds
|
2.5 ba
|
3604 sqft
MLS® 73581571Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Lynne Russo
Property at 6 Aricia Ln, Winchester, MA 01890
1 / 34
Active
Open

$1,399,000

6 Aricia Ln, Winchester, MA 01890

3 bds
|
2.5 ba
|
1975 sqft
MLS® 73590311Single Family Residence
Gibson Sotheby's International Realty - Pirani & Wile Group
Property at 14 Nassau Drive, Winchester, MA 01890
1 / 30
Active
Price

$2,750,000

14 Nassau Drive, Winchester, MA 01890

6 bds
|
6 ba
|
6968 sqft
MLS® 73500890Single Family Residence
WINN Real Estate & Consulting - Weidong Li
Property at 258 Cross St, Winchester, MA 01890
1 / 34
Active

$974,900

258 Cross St, Winchester, MA 01890

3 bds
|
2.5 ba
|
1719 sqft
MLS® 73575764Single Family Residence
Fiv Realty Co - Justin Blankenship
Property at 1 Town Way, Winchester, MA 01890
1 / 41
Active
Price

$1,749,000

1 Town Way, Winchester, MA 01890

3 bds
|
3.5 ba
|
3010 sqft
MLS® 73555777Single Family Residence
Compass - Vita Realty Group
Property at 276 High Street, Winchester, MA 01890
1 / 41
Active
Price

$2,195,000

276 High Street, Winchester, MA 01890

5 bds
|
3.5 ba
|
5006 sqft
MLS® 73496396Single Family Residence
Compass - Kim Covino & Co. Team
Property at 4 Dartmouth, Winchester, MA 01890
1 / 38
Active

$4,299,000

4 Dartmouth, Winchester, MA 01890

5 bds
|
5.5 ba
|
6526 sqft
MLS® 73574948Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 117 Highland, Winchester, MA 01890
1 / 42
Active

$1,650,000

117 Highland, Winchester, MA 01890

5 bds
|
3.5 ba
|
3722 sqft
MLS® 73573887Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Dara Singleton
Property at 54 Squire Road, Winchester, MA 01890
1 / 42
Active
Price
Open

$2,399,000

54 Squire Road, Winchester, MA 01890

4 bds
|
4.5 ba
|
4450 sqft
MLS® 73555666Single Family Residence
The Marino Group Collection - Anthony Marino
Page 1 of 2

Brokerage Information

Compass

1330 Boylston Street, Chestnut Hill, MA, 02467

(917) 952-9966

Market Area Served

Needham, Weston, Natick, Brookline, Newton, Wellesley, Dover and many more.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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The Samantha Eisenberg Group

We're The Samantha Eisenberg Group at Compass, helping buyers and sellers in Needham, Newton and Wellesley with a lawyer-led negotiating edge. Let's talk.

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  • (917) 952-9966
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Equal Housing Opportunity. Information deemed reliable but not guaranteed.

Service Areas

  • Wellesley, MA
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  • Newton, MA
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  • Weston, MA
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Office

  • Compass - Chestnut Hill, MA

    1330 Boylston Street

    Chestnut Hill, MA 02467

    (917) 952-9966

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

As of October 27, 2026, there are 47 single-family homes for sale in Winchester, MA, with a median list price of $1,750,000. In July 2026, the median sale price for homes in Winchester, MA (all home types) was $1,775,000, up 38.7% from a year earlier.

Houses for sale
47
Median list price
$1,750,000
Median sale price (July 2026, all home types)
$1,775,000
Median days on market (July 2026, all home types)
22 days
  • Winchester market report

Homes for sale near Winchester

  • Woburn, MA
  • West Medford, MA
  • Arlington Heights, MA
  • Medford, MA
  • Stoneham, MA
  • Arlington, MA
  • Lexington, MA
  • Melrose, MA

Common questions about Winchester, MA real estate

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

As of October 27, 2026, there are 47 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 $1,750,000. Homes (all home types) that sold in July 2026 had a median sale price of $1,775,000, up 38.7% from a year earlier.

How long do homes take to sell in Winchester, MA?

Homes (all home types) in Winchester, MA that sold in July 2026 had a median of 22 days on market. Single-family homes currently for sale show a median of about 25 days on market.