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Homes for Sale in Winchester, MA

51 results

Property at 8-10 Oak St, Winchester, MA 01890
1 / 38
Active
Open

$1,125,000

8-10 Oak St, Winchester, MA 01890

5 bds
|
2.5 ba
|
2391 sqft
MLS® 73555245Multi Family
The Synergy Group - The Synergy Group
Property at 15 Clark St, Winchester, MA 01890
1 / 22
Active

$849,000

15 Clark St, Winchester, MA 01890

3 bds
|
1.5 ba
|
1340 sqft
MLS® 73555218Single Family Residence
Coldwell Banker Realty - Milton - Jeffrey Hsu
Property at 6 Davey Ln, Winchester, MA 01890
1 / 34
Active

$2,225,000

6 Davey Ln, Winchester, MA 01890

4 bds
|
3 ba
|
4210 sqft
MLS® 73554545Single Family Residence
Provided by MLS PIN - Gretchen Papineau
Property at 241 Ridge St, Winchester, MA 01890
1 / 37
Active

$1,599,000

241 Ridge St, Winchester, MA 01890

4 bds
|
3 ba
|
2480 sqft
MLS® 73554036Single Family Residence
Lillian Montalto Signature Properties - Team Lillian Montalto
Property at 11 Williams Cir, Winchester, MA 01890
1 / 39
Active

$1,150,000

11 Williams Cir, Winchester, MA 01890

4 bds
|
2.5 ba
|
2392 sqft
MLS® 73554139Single Family Residence
Barrett Sotheby's International Realty - Anne Spry

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.

Property at 15 Clark St #15, Winchester, MA 01890
1 / 24
Active

$849,000

15 Clark St #15, Winchester, MA 01890

3 bds
|
1.5 ba
|
1340 sqft
MLS® 73553626Condex
Coldwell Banker Realty - Milton - Jeffrey Hsu
Property at 666 Main #211, Winchester, MA 01890
1 / 42
Active

$700,000

666 Main #211, Winchester, MA 01890

2 bds
|
2 ba
|
1170 sqft
MLS® 73553517Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 257 Cross St, Winchester, MA 01890
1 / 39
Active

$1,099,000

257 Cross St, Winchester, MA 01890

5 bds
|
2.5 ba
|
2801 sqft
MLS® 73553083Multi Family
Compass - Kim Covino & Co. Team
Property at 18 Graystone Circle #18, Winchester, MA 01890
1 / 42
Active Under Contract

$1,750,000

18 Graystone Circle #18, Winchester, MA 01890

3 bds
|
2.5 ba
|
2833 sqft
MLS® 73551306Condominium
Compass - Kim Covino & Co. Team
Property at 47 Water Street, Winchester, MA 01890
1 / 30
Active

$950,000

47 Water Street, Winchester, MA 01890

3 bds
|
1 ba
|
1356 sqft
MLS® 73549935Single Family Residence
Leading Edge Real Estate - The Mary Scimemi Team
Property at 247 Washington St #11, Winchester, MA 01890
1 / 23
Active

$729,000

247 Washington St #11, Winchester, MA 01890

3 bds
|
2.5 ba
|
1494 sqft
MLS® 73549877Condominium
Blue Ocean Realty, LLC - Heejeong Joo
Property at 52 Salem Street #52, Winchester, MA 01890
1 / 28
Active Under Contract

$1,150,000

52 Salem Street #52, Winchester, MA 01890

3 bds
|
2.5 ba
|
2004 sqft
MLS® 73549484Condominium
Better Homes and Gardens Real Estate - The Shanahan Group - Michael Rauseo
Property at 2 Olde Lyme Road, Winchester, MA 01890
1 / 42
Active Under Contract

$1,699,000

2 Olde Lyme Road, Winchester, MA 01890

3 bds
|
3.5 ba
|
2513 sqft
MLS® 73549106Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Paula R. Sughrue
Property at 200 Swanton #L8, Winchester, MA 01890
1 / 28
Active

$288,750

200 Swanton #L8, Winchester, MA 01890

1 bds
|
1 ba
|
388 sqft
MLS® 73548413Condominium
Cameron Real Estate Group - Stephen Deconto
Property at 10 Dartmouth Street, Winchester, MA 01890
1 / 42
Active

$2,999,000

10 Dartmouth Street, Winchester, MA 01890

5 bds
|
3 ba
|
4028 sqft
MLS® 73548103Single Family Residence
Compass - Kim Covino & Co. Team
Property at 46 Clark St, Winchester, MA 01890
1 / 36
Active

$1,064,000

46 Clark St, Winchester, MA 01890

4 bds
|
1.5 ba
|
1777 sqft
MLS® 73547513Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty
Property at 50 Middlesex Street #50, Winchester, MA 01890
1 / 21
Active

$799,000

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 79 Grove St, Winchester, MA 01890
1 / 41
Active

$1,899,000

79 Grove St, Winchester, MA 01890

5 bds
|
3.5 ba
|
3210 sqft
MLS® 73545952Single Family Residence
Provided by MLS PIN - Pirani & Wile Group
Property at 52 Middlesex Street #52, Winchester, MA 01890
1 / 41
Active Under Contract

$1,195,000

52 Middlesex Street #52, Winchester, MA 01890

4 bds
|
2.5 ba
|
2303 sqft
MLS® 73546076Condominium
Keller Williams Realty Evolution - The North Star Group
Property at 9 Plymouth Rd, Winchester, MA 01890
1 / 37
Active

$2,500,000

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 #315, Winchester, MA 01890
1 / 37
Active

$649,900

666 Main Street #315, Winchester, MA 01890

2 bds
|
2 ba
|
1025 sqft
MLS® 73543744Condominium
Compass - Kim Covino & Co. Team
Property at 84 Oak Street, Winchester, MA 01890
1 / 40
Active

$888,000

84 Oak Street, Winchester, MA 01890

4 bds
|
2 ba
|
2083 sqft
MLS® 73542597Single Family Residence
Charlesgate Realty Group LLC - John E. Magazzu
Property at 423 Washington St, Winchester, MA 01890
1 / 42
Active

$1,350,000

423 Washington St, Winchester, MA 01890

4 bds
|
3 ba
|
2690 sqft
MLS® 73541775Single Family Residence
MA Properties - Danielle Fleming
Property at 258 Cross Street, Winchester, MA 01890
1 / 40
Active

$999,900

258 Cross Street, Winchester, MA 01890

4 bds
|
2 ba
|
1719 sqft
MLS® 73541288Single Family Residence
Hartley Realty Group - Justin Blankenship
Property at 14 Hillside Ave, Winchester, MA 01890
1 / 40
Active

$2,300,000

14 Hillside Ave, Winchester, MA 01890

4 bds
|
4.5 ba
|
3881 sqft
MLS® 73541163Single Family Residence
East West Real Estate, LLC - Rebecca Huang
Property at 150 Cambridge Street, Winchester, MA 01890
1 / 42
Active

$1,099,000

150 Cambridge Street, Winchester, MA 01890

3 bds
|
1.5 ba
|
1711 sqft
MLS® 73530959Single Family Residence
Plunkett Properties - Diane Plunkett
Property at 26 N Gateway, Winchester, MA 01890
1 / 36
Active

$2,099,000

26 N Gateway, Winchester, MA 01890

4 bds
|
3.5 ba
|
3210 sqft
MLS® 73538052Single Family Residence
Provided by MLS PIN - Pirani & Wile Group
Property at 117 Highland Ave, Winchester, MA 01890
1 / 40
Active

$1,675,000

117 Highland Ave, Winchester, MA 01890

5 bds
|
3.5 ba
|
3722 sqft
MLS® 73538393Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Dara Singleton
Property at 38 Robinhood Rd, Winchester, MA 01890
1 / 32
Active

$1,175,000

38 Robinhood Rd, Winchester, MA 01890

3 bds
|
2 ba
|
1736 sqft
MLS® 73537786Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Catherine Albiani
Property at 15 Fieldstone Dr, Winchester, MA 01890
1 / 42
Active Under Contract

$1,925,000

15 Fieldstone Dr, Winchester, MA 01890

4 bds
|
3.5 ba
|
3286 sqft
MLS® 73537676Single Family Residence
Barrett Sotheby's International Realty - Anne Spry
Page 1 of 2

Brokerage Information

Block / AD Advisors

1404 Beacon Street, Brookline, MA, 02446

(617) 869-4907

Market Area Served

Brookline, Boston, Winthrop, Somerville, Cambridge, Newton, Needham, Dedham, Norwood, Watertown, Waltham, Revere, Westwood, Medford, Ashland, Framingham 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.

Data last updated: 7/27/2026 at 9:30:00 PM

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