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60+ Homes for Sale in Winchester, MA

68 results

Property at 42 Everett Ave, Winchester, MA 01890
1 / 40
Active

$2,199,000

42 Everett Ave, Winchester, MA 01890

6 bds
|
4 ba
|
4947 sqft
MLS® 73588192Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 200 Swanton St #T14, Winchester, MA 01890
1 / 26
Active Under Contract
Price

$319,000

200 Swanton St #T14, Winchester, MA 01890

1 bds
|
1 ba
|
602 sqft
MLS® 73580409Condominium
The Synergy Group - The Synergy Group
Property at 30 Surrey Rd, Winchester, MA 01890
1 / 24
Coming Soon

$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 1 Overlook Way, Winchester, MA 01890
1 / 40
Active

$1,850,000

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 4 Churchill Road, Winchester, MA 01890
1 / 42
Active
Price

$1,649,000

4 Churchill Road, Winchester, MA 01890

3 bds
|
2 ba
|
2421 sqft
MLS® 73572661Single Family Residence
Compass - Kim Covino & Co. Team

What's actually happening in Winchester right now?

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Property at 21 Amberwood Dr, Winchester, MA 01890
1 / 42
Active

$2,049,000

21 Amberwood Dr, Winchester, MA 01890

5 bds
|
3.5 ba
|
4063 sqft
MLS® 73588059Single Family Residence
Compass - Gayle Winters & Co. Team
Property at 20 Arthur St #20, Winchester, MA 01890
Active

$329,900

20 Arthur St #20, Winchester, MA 01890

2 bds
|
1 ba
|
1084 sqft
MLS® 73587970Condex
LAER Realty Partners - Dan O'Connell Sr
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 39 Forest St, Winchester, MA 01890
1 / 38
Active

$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 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

$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 63 Wedgemere Avenue, Winchester, MA 01890
1 / 39
Active

$2,399,000

63 Wedgemere Avenue, Winchester, MA 01890

4 bds
|
3 ba
|
3550 sqft
MLS® 73587441Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Paula R. Sughrue
Property at 143 Arlington Street, Winchester, MA 01890
1 / 42
Active Under Contract

$1,599,000

143 Arlington Street, Winchester, MA 01890

5 bds
|
2 ba
|
2944 sqft
MLS® 73575069Single Family Residence
Compass - Kim Covino & Co. Team
Property at 15 Lloyd Street, Winchester, MA 01890
1 / 41
Active

$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 189 Washington St #2, Winchester, MA 01890
1 / 38
Active
Price

$765,000

189 Washington St #2, Winchester, MA 01890

3 bds
|
2 ba
|
1643 sqft
MLS® 73575116Condominium
Compass - Kim Covino & Co. Team
Property at 200 Swanton St #717, Winchester, MA 01890
1 / 30
Active
Price

$349,900

200 Swanton St #717, Winchester, MA 01890

1 bds
|
1 ba
|
613 sqft
MLS® 73500952Condominium
Coldwell Banker Realty - Lexington - Cameron Moniz
Property at 39 Henry Street, Winchester, MA 01890
1 / 23
Active

$899,000

39 Henry Street, Winchester, MA 01890

3 bds
|
1 ba
|
1313 sqft
MLS® 73585414Single Family Residence
Coldwell Banker Realty - Belmont - Kelly Batti
Property at 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 7 Sherman Place #7, Winchester, MA 01890
1 / 42
Active

$1,495,000

7 Sherman Place #7, Winchester, MA 01890

4 bds
|
2.5 ba
|
2973 sqft
MLS® 73577640Condominium
Engel & Volkers Boston - John Dean
Property at 7 Wainwright Road #113, Winchester, MA 01890
1 / 42
Active
Price

$1,999,000

7 Wainwright Road #113, Winchester, MA 01890

4 bds
|
3.5 ba
|
3640 sqft
MLS® 73556476Condominium
Compass - Kim Covino & Co. Team
Property at 666 Main Street #217, Winchester, MA 01890
1 / 41
Active

$700,000

666 Main Street #217, Winchester, MA 01890

2 bds
|
2 ba
|
1240 sqft
MLS® 73581469Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 666 Main Street #211, Winchester, MA 01890
1 / 42
Active
Price

$685,000

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 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 26 Mayflower Road, Winchester, MA 01890
1 / 42
Active Under Contract

$1,950,000

26 Mayflower Road, Winchester, MA 01890

5 bds
|
4 ba
|
3371 sqft
MLS® 73584117Single Family Residence
The Simply Sold Realty Co. - Nicole M. Condon
Property at 79 Grove St, Winchester, MA 01890
1 / 42
Active Under Contract
Price

$1,870,000

79 Grove St, Winchester, MA 01890

5 bds
|
3.5 ba
|
3210 sqft
MLS® 73545952Single Family Residence
Gibson Sotheby's International Realty - Pirani & Wile Group
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 4 Stone Ave, Winchester, MA 01890
1 / 38
Active

$1,195,000

4 Stone Ave, Winchester, MA 01890

3 bds
|
1.5 ba
|
2239 sqft
MLS® 73582171Single Family Residence
The Synergy Group - The Synergy Group
Property at 54 Squire Road, Winchester, MA 01890
1 / 42
Active
Price

$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
Property at 15 Vinson Circle, Winchester, MA 01890
1 / 42
Active

$18,000,000

15 Vinson Circle, Winchester, MA 01890

6 bds
|
6.5 ba
|
10000 sqft
MLS® 73585235Single Family Residence
The Marino Group Collection - Anthony Marino
Page 1 of 3

Brokerage Information

Gundersheim Group Real Estate

10 Lincoln St, Newton, MA, 02461

(617) 997-8272

Market Area Served

Boston, Somerville, Newton, Wellesley, Needham, Brookline 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.

Melanie Gundersheim

Buy or sell in Boston, Newton, Needham, Brookline, Wellesley, and Somerville with clear guidance, local insight, and a calm, strategic process.

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

As of October 12, 2026, there are 68 homes for sale in Winchester, MA, with a median list price of $1,512,000. 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
68
Median list price
$1,512,000
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 12, 2026, there are 68 homes for sale in Winchester, MA, including 50 single-family homes, 15 condos and 1 multi-family home.

What is the median home price in Winchester, MA?

The median list price of homes for sale in Winchester, MA is $1,512,000. 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 29 days on market.

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

The homes for sale in Winchester, MA include 50 single-family homes, 15 condos and 1 multi-family home.