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Houses for Sale in Winchester, MA

33 results

Property at 1 Town Way, Winchester, MA 01890
1 / 42
Active

$1,799,000

1 Town Way, Winchester, MA 01890

3 bds
|
3.5 ba
|
3010 sqft
MLS® 73555777Single Family Residence
Compass - Vita Realty Group
Property at 8 Oak Street, Winchester, MA 01890
1 / 38
Active
Open

$1,125,000

8 Oak Street, Winchester, MA 01890

5 bds
|
2.5 ba
|
2391 sqft
MLS® 73555597Single Family Residence
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

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 11 Williams Cir, Winchester, MA 01890
1 / 39
Active Under Contract

$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
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 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 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
Open

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

$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 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 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
Open

$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 78 Bacon Street, Winchester, MA 01890
1 / 42
Active

$2,499,000

78 Bacon Street, Winchester, MA 01890

5 bds
|
3.5 ba
|
5230 sqft
MLS® 73526460Single Family Residence
Compass - Kim Covino & Co. Team
Property at 53 Winford Way, Winchester, MA 01890
1 / 24
Active
Open

$2,399,000

53 Winford Way, Winchester, MA 01890

5 bds
|
4 ba
|
5083 sqft
MLS® 73525195Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty
Property at 8 Hawthorne Road, Winchester, MA 01890
1 / 27
Active Under Contract

$1,825,000

8 Hawthorne Road, Winchester, MA 01890

5 bds
|
3 ba
|
3315 sqft
MLS® 73522773Single Family Residence
Coldwell Banker Realty - Lexington - H. Elaine Song
Property at 53 Lake Street, Winchester, MA 01890
1 / 42
Active

$1,199,000

53 Lake Street, Winchester, MA 01890

3 bds
|
2.5 ba
|
2235 sqft
MLS® 73519082Single Family Residence
Compass - Kim Covino & Co. Team
Property at 18 Middlesex St, Winchester, MA 01890
1 / 32
Active

$2,795,000

18 Middlesex St, Winchester, MA 01890

4 bds
|
4.5 ba
|
5233 sqft
MLS® 73518621Single Family Residence
Luxury Living Real Estate - Tina Natale
Property at 8 Priscilla Ln, Winchester, MA 01890
1 / 36
Active

$3,149,000

8 Priscilla Ln, Winchester, MA 01890

5 bds
|
5.5 ba
|
6500 sqft
MLS® 73513501Single Family Residence
LAER Realty Partners - The Pezzano Group
Property at 16 & 16A Glenwood Ave, Winchester, MA 01890
1 / 41
Active

$1,899,000

16 & 16A Glenwood Ave, Winchester, MA 01890

6 bds
|
4.5 ba
|
6900 sqft
MLS® 73507137Single Family Residence
Compass - Kim Covino & Co. Team
Property at 37 Mayflower Road, Winchester, MA 01890
1 / 40
Active

$3,179,000

37 Mayflower Road, Winchester, MA 01890

7 bds
|
7.5 ba
|
8540 sqft
MLS® 73502853Single Family Residence
Compass - Kim Covino & Co. Team
Property at 14 Nassau Drive, Winchester, MA 01890
1 / 30
Active

$2,799,000

14 Nassau Drive, Winchester, MA 01890

6 bds
|
6 ba
|
6968 sqft
MLS® 73500890Single Family Residence
WINN Real Estate & Consulting - Weidong Li
Property at 380 Cross Street, Winchester, MA 01890
1 / 41
Active

$929,900

380 Cross Street, Winchester, MA 01890

4 bds
|
2 ba
|
1938 sqft
MLS® 73498603Single Family Residence
Coldwell Banker Realty - Lexington - Rajive Dogra
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Brokerage Information

Commonwealth Standard Realty

10 Lincoln Street, Newton, MA 02461, USA

(617) 645-4086

Market Area Served

Newton, Wellesley, Needham, Brookline, Natick, Lexington, Westwood, Medfield, Belmont, Watertown, Dedham, Boston, Wayland 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: 7/28/2026 at 4:36:00 PM

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