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Homes for Sale in Winchester, MA

30 results

Property at 15 Gershon Way #15, Winchester, MA 01890
1 / 35
Active
Open

$2,395,000

15 Gershon Way #15, Winchester, MA 01890

3 bds
|
4 ba
|
4087 sqft
MLS® 73495315Condominium
Coldwell Banker Realty - Wellesley - Moira Lown
Property at 15 Gershon Way #15, Winchester, MA 01890
1 / 35
Active
Open

$2,395,000

15 Gershon Way #15, Winchester, MA 01890

3 bds
|
4 ba
|
4087 sqft
MLS® 73495350Single Family Residence
Coldwell Banker Realty - Wellesley - Moira Lown
Property at 15 East Street, Winchester, MA 01890
1 / 39
Active

$1,199,000

15 East Street, Winchester, MA 01890

3 bds
|
2 ba
|
1973 sqft
MLS® 73493684Single Family Residence
Compass - Kim Covino & Co. Team
Property at 2 Abby Rd, Winchester, MA 01890
1 / 35
Active

$2,649,000

2 Abby Rd, Winchester, MA 01890

4 bds
|
5 ba
|
5614 sqft
MLS® 73492061Single Family Residence
Leading Edge Real Estate - The Pallotta Group
Property at 15 Edward Drive #15, Winchester, MA 01890
1 / 42
Active

$958,000

15 Edward Drive #15, Winchester, MA 01890

3 bds
|
3 ba
|
2082 sqft
MLS® 73492749Condominium
Coldwell Banker Realty - Lexington - Alina Wang Team

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Property at 12 Wincrest Drive, Winchester, MA 01890
1 / 41
Active Under Contract

$1,750,000

12 Wincrest Drive, Winchester, MA 01890

6 bds
|
5 ba
|
3833 sqft
MLS® 73492714Single Family Residence
Compass - Kim Covino & Co. Team
Property at 76 Woodside Road, Winchester, MA 01890
1 / 25
Active Under Contract

$999,000

76 Woodside Road, Winchester, MA 01890

4 bds
|
2 ba
|
1552 sqft
MLS® 73492483Single Family Residence
Pierce Properties Real Estate - Michael Pierce
Property at 29 Pilgrim Dr, Winchester, MA 01890
1 / 42
Active

$1,749,000

29 Pilgrim Dr, Winchester, MA 01890

5 bds
|
3 ba
|
3271 sqft
MLS® 73491480Single Family Residence
Barrett Sotheby's International Realty - Anne Spry
Property at 56 Yale Street, Winchester, MA 01890
1 / 42
Active Under Contract

$2,795,000

56 Yale Street, Winchester, MA 01890

5 bds
|
4 ba
|
4792 sqft
MLS® 73491616Single Family Residence
Brad Hutchinson Real Estate - Patricia Fitzgerald
Property at 171 Swanton St #21, Winchester, MA 01890
1 / 40
Active Under Contract

$749,900

171 Swanton St #21, Winchester, MA 01890

3 bds
|
3 ba
|
1834 sqft
MLS® 73491180Condominium
Colby Hunter Realty - Jesse Mason
Property at 10 Edgehill Road, Winchester, MA 01890
1 / 42
Active Under Contract

$2,250,000

10 Edgehill Road, Winchester, MA 01890

7 bds
|
4 ba
|
3926 sqft
MLS® 73490604Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Lynne Russo
Property at 58 Jefferson Road, Winchester, MA 01890
1 / 37
Active Under Contract

$1,799,000

58 Jefferson Road, Winchester, MA 01890

4 bds
|
3 ba
|
2910 sqft
MLS® 73488901Single Family Residence
Premier Realty Group, Inc. - Stephanie Macfarland
Property at 2 Everett Ave, Winchester, MA 01890
1 / 41
Active

$3,747,000

2 Everett Ave, Winchester, MA 01890

7 bds
|
6 ba
|
7043 sqft
MLS® 73488991Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Joan Francis Sullivan
Property at 10 Dartmouth Street, Winchester, MA 01890
1 / 42
Active

$3,299,000

10 Dartmouth Street, Winchester, MA 01890

5 bds
|
4 ba
|
4028 sqft
MLS® 73488384Single Family Residence
Compass - Kim Covino & Co. Team
Property at 34 Robinhood Road, Winchester, MA 01890
1 / 37
Active

$1,524,000

34 Robinhood Road, Winchester, MA 01890

4 bds
|
3 ba
|
3380 sqft
MLS® 73486878Single Family Residence
RE/MAX Destiny - Janet Halloran
Property at 40 Foxcroft Rd, Winchester, MA 01890
1 / 42
Active

$3,650,000

40 Foxcroft Rd, Winchester, MA 01890

6 bds
|
5 ba
|
6460 sqft
MLS® 73485774Single Family Residence
Provided by MLS PIN - The Boston One Team
Property at 65 High Street, Winchester, MA 01890
1 / 26
Active

$1,499,999

65 High Street, Winchester, MA 01890

6 bds
|
3 ba
|
2658 sqft
MLS® 73485189Single Family Residence
K Stadium Realty - Anna Jung
Property at 666 Main St #315, Winchester, MA 01890
1 / 23
Active

$688,000

666 Main St #315, Winchester, MA 01890

2 bds
|
2 ba
|
1025 sqft
MLS® 73485732Condominium
Peace of Mind Realty - Jing Chen
Property at 4 Dartmouth St, Winchester, MA 01890
1 / 42
Active

$4,699,000

4 Dartmouth St, Winchester, MA 01890

5 bds
|
6 ba
|
6526 sqft
MLS® 73482952Single Family Residence
Leading Edge Real Estate - The Pallotta Group
Property at 9 Albamont Road, Winchester, MA 01890
1 / 10
Active

$3,400,000

9 Albamont Road, Winchester, MA 01890

6 bds
|
6 ba
|
6100 sqft
MLS® 73482275Single Family Residence
Compass - Kim Covino & Co. Team
Property at 53 Winford Way, Winchester, MA 01890
1 / 16
Active

$2,799,000

53 Winford Way, Winchester, MA 01890

5 bds
|
4 ba
|
5083 sqft
MLS® 73481323Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty
Property at 37 Mayflower Road, Winchester, MA 01890
1 / 42
Active

$3,537,000

37 Mayflower Road, Winchester, MA 01890

7 bds
|
8 ba
|
8540 sqft
MLS® 73475646Single Family Residence
Compass - Kim Covino & Co. Team
Property at 15 Mayflower Rd, Winchester, MA 01890
1 / 39
Active

$3,425,000

15 Mayflower Rd, Winchester, MA 01890

7 bds
|
8 ba
|
7226 sqft
MLS® 73474189Single Family Residence
Douglas Elliman Real Estate - The Sarkis Team - The Sarkis Team
Property at 54 Johnson Rd, Winchester, MA 01890
1 / 42
Active

$3,499,000

54 Johnson Rd, Winchester, MA 01890

5 bds
|
8 ba
|
6899 sqft
MLS® 73474290Single Family Residence
Compass - Kim Covino & Co. Team
Property at 25 Myopia Road, Winchester, MA 01890
1 / 31
Active

$3,390,000

25 Myopia Road, Winchester, MA 01890

4 bds
|
4 ba
|
4847 sqft
MLS® 73471735Single Family Residence
Engel & Volkers Boston - Wenjun Cao
Property at 27 Everett Ave, Winchester, MA 01890
1 / 39
Active

$3,290,000

27 Everett Ave, Winchester, MA 01890

6 bds
|
6 ba
|
7431 sqft
MLS® 73468691Single Family Residence
Leading Edge Real Estate - The Pallotta Group
Property at 1 Town Way, Winchester, MA 01890
1 / 40
Active

$1,899,000

1 Town Way, Winchester, MA 01890

3 bds
|
4 ba
|
3010 sqft
MLS® 73466233Single Family Residence
Compass - Vita Realty Group
Property at 237 Swanton Street, Winchester, MA 01890
1 / 35
Active

$1,945,000

237 Swanton Street, Winchester, MA 01890

5 bds
|
4 ba
|
4334 sqft
MLS® 73459838Single Family Residence
Compass - Kim Covino & Co. Team
Property at 200 Swanton St #228, Winchester, MA 01890
1 / 26
Active

$379,000

200 Swanton St #228, Winchester, MA 01890

1 bds
|
1 ba
|
606 sqft
MLS® 73459781Condominium
Keller Williams Realty Evolution - Joan Powell
Property at 20 Amberwood Dr, Winchester, MA 01890
1 / 36
Active

$3,600,000

20 Amberwood Dr, Winchester, MA 01890

6 bds
|
7 ba
|
8866 sqft
MLS® 73423693Single Family Residence
Coldwell Banker Realty - Lexington - Wei Wang

Brokerage Information

Commonwealth Standard Realty

10 Lincoln Street, Newton, MA, USA

(617) 997-8272

Market Area Served

Boston, Newton, Needham, Brookline, Wellesley, Somerville

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: 4/4/2026 at 5:53:00 PM