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60+ Homes for Sale in Winchester, MA

65 results

Property at 28 Olive St, Winchester, MA 01890
1 / 8
Active
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 1 Plymouth Rd., Winchester, MA 01890
1 / 28
Active

$3,299,000

1 Plymouth Rd., Winchester, MA 01890

7 bds
|
7.5 ba
|
7226 sqft
MLS® 73585058Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 7 Hutchinson Road, Winchester, MA 01890
1 / 42
Active
Open

$3,450,000

7 Hutchinson Road, Winchester, MA 01890

6 bds
|
4.5 ba
|
5735 sqft
MLS® 73561703Single Family Residence
Compass - Kim Covino & Co. Team
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 30 Willowdale Rd, Winchester, MA 01890
1 / 41
Active
Open

$3,200,000

30 Willowdale Rd, Winchester, MA 01890

8 bds
|
6.5 ba
|
5750 sqft
MLS® 73577116Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group

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Property at 257 Cross Street, Winchester, MA 01890
1 / 40
Active

$1,050,000

257 Cross Street, Winchester, MA 01890

5 bds
|
2.5 ba
|
2801 sqft
MLS® 73571418Single Family Residence
Compass - Kim Covino & Co. Team
Property at 3 Sunset Road, Winchester, MA 01890
1 / 42
Active
New
Open

$1,699,000

3 Sunset Road, Winchester, MA 01890

4 bds
|
2.5 ba
|
2736 sqft
MLS® 73596720Single Family Residence
Compass - Kim Covino & Co. Team
Property at 54 Squire Road, Winchester, MA 01890
1 / 42
Active
Price

$2,299,000

54 Squire Road, Winchester, MA 01890

4 bds
|
4.5 ba
|
4450 sqft
MLS® 73555666Single Family Residence
The Marino Group Collection - Anthony Marino
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
MLS® 73589478Single Family Residence
Barrett Sotheby's International Realty - Anne Spry
Property at 67-69 Hemingway St, Winchester, MA 01890
1 / 6
Active
New

$1,450,000

67-69 Hemingway St, Winchester, MA 01890

0 bds
|
0 ba
|
-- sqft
MLS® 73595844Residential
Gibson Sotheby's International Realty - Pirani & Wile Group
Property at 18 Middlesex St, Winchester, MA 01890
1 / 32
Active
Open

$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
Open

$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 1 Overlook Way, Winchester, MA 01890
1 / 41
Active
Price
Open

$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 16-18 Russell Rd, Winchester, MA 01890
1 / 43
Active
Open

$1,049,000

16-18 Russell Rd, Winchester, MA 01890

4 bds
|
2 ba
|
2226 sqft
MLS® 735945132 Family - 2 Units Up/Down
Keller Williams Realty Boston Northwest - Andersen Group Realty
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 666 Main Street #211, Winchester, MA 01890
1 / 42
Active
Price

$664,000

666 Main Street #211, Winchester, MA 01890

2 bds
|
2 ba
|
1170 sqft
MLS® 73553517Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
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 67-69 Hemingway St, Winchester, MA 01890
1 / 6
Active

$1,450,000

67-69 Hemingway St, Winchester, MA 01890

8 bds
|
5 ba
|
6200 sqft
MLS® 73594547Multi Family
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
Open

$850,000

39 Henry Street, Winchester, MA 01890

3 bds
|
1 ba
|
1313 sqft
MLS® 73585414Single Family Residence
Coldwell Banker Realty - Belmont - Kelly Batti
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 247 Washington St #11, Winchester, MA 01890
1 / 23
Active
Price

$600,000

247 Washington St #11, Winchester, MA 01890

3 bds
|
2.5 ba
|
1494 sqft
MLS® 73549877Condominium
Coldwell Banker Realty - Lexington - Heejeong Joo
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 465 Washington Street #465, Winchester, MA 01890
1 / 28
Active
Price

$1,250,000

465 Washington Street #465, Winchester, MA 01890

4 bds
|
2.5 ba
|
2666 sqft
MLS® 73574929Condominium
Gibson Sotheby's International Realty - The Pallotta Group
Property at 50 Middlesex Street #50, Winchester, MA 01890
1 / 21
Active
Price

$769,000

50 Middlesex Street #50, Winchester, MA 01890

2 bds
|
2 ba
|
1036 sqft
MLS® 73546074Condominium
Keller Williams Realty Evolution - The North Star Group
Property at 419-421 Washington St, Winchester, MA 01890
1 / 16
Active
Open

$1,299,000

419-421 Washington St, Winchester, MA 01890

6 bds
|
2 ba
|
2946 sqft
MLS® 73592723Multi Family
Coldwell Banker Realty - Lexington - The Marrocco Group
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
Open

$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
Page 1 of 3

Brokerage Information

Commonwealth Standard Realty Advisors

10 Lincoln St, Newton, MA, 02461

(617) 256-7438

Market Area Served

Boston, Brookline, Cambridge, Medford, Somerville, Newton 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.

Andrew Goldberg

I'm Andrew Goldberg, a Boston real estate advisor specializing in first-time buyers across Greater Boston. I guide you A to Z—from first search to closing day.

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Equal Housing Opportunity. Information deemed reliable but not guaranteed.

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

As of October 30, 2026, there are 65 homes for sale in Winchester, MA, with a median list price of $1,450,000. In July 2026, the median sale price for homes in Winchester, MA was $1,775,000, up 38.7% from a year earlier.

Homes for sale
65
Median list price
$1,450,000
Median sale price (July 2026)
$1,775,000
Median days on market (July 2026)
22 days
  • Winchester market report
  • Winchester single-family homes for sale
  • Winchester condos for sale
  • Winchester multi-family homes for sale

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 homes are for sale in Winchester, MA?

As of October 30, 2026, there are 65 homes for sale in Winchester, MA, including 46 single-family homes, 13 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 $1,450,000. Homes 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 in Winchester, MA that sold in July 2026 had a median of 22 days on market. Homes currently for sale show a median of about 35 days on market.

What types of homes are for sale in Winchester, MA?

The homes for sale in Winchester, MA include 46 single-family homes, 13 condos and 4 multi-family homes.