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Homes for Sale in Winchester, MA

49 results

Property at 85 High St, Winchester, MA 01890
1 / 38
Active
New
Open

$1,999,000

85 High St, Winchester, MA 01890

4 bds
|
2.5 ba
|
3757 sqft
MLS® 73565817Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Catherine Albiani
Property at 10 Rangeley Road, Winchester, MA 01890
1 / 42
Active

$3,199,000

10 Rangeley Road, Winchester, MA 01890

5 bds
|
4.5 ba
|
5406 sqft
MLS® 73561672Single Family Residence
Compass - Karima Alami
Property at 2 Atherton Rd, Winchester, MA 01890
1 / 42
Active

$3,295,000

2 Atherton Rd, Winchester, MA 01890

6 bds
|
6.5 ba
|
6100 sqft
MLS® 73563095Single Family Residence
Provided by MLS PIN - Peter Kasseris
Property at 110 Thornberry Road, Winchester, MA 01890
1 / 34
Active
Price
Open

$1,399,000

110 Thornberry Road, Winchester, MA 01890

3 bds
|
2.5 ba
|
2459 sqft
MLS® 73562273Single Family Residence
Kiklis Real Estate, LLC - Mark Kiklis
Property at 20 Sargent Rd, Winchester, MA 01890
1 / 39
Active Under Contract

$1,529,000

20 Sargent Rd, Winchester, MA 01890

3 bds
|
2.5 ba
|
1956 sqft
MLS® 73562422Single 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 54 Squire Road, Winchester, MA 01890
1 / 42
Active

$2,499,000

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 96 Loring Ave, Winchester, MA 01890
1 / 29
Active
Open

$949,999

96 Loring Ave, Winchester, MA 01890

4 bds
|
2 ba
|
2326 sqft
MLS® 73561829Single Family Residence
StartPoint Realty - Jeremy Smith
Property at 18 Ridge St, Winchester, MA 01890
1 / 4
Active

$3,200,000

18 Ridge St, Winchester, MA 01890

5 bds
|
5.5 ba
|
5295 sqft
MLS® 73561372Single Family Residence
Compass - Gayle Winters & Co. Team
Property at 7 Hutchinson Road, Winchester, MA 01890
1 / 42
Active

$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 5 Forest Cir, Winchester, MA 01890
1 / 10
Active

$2,999,000

5 Forest Cir, Winchester, MA 01890

4 bds
|
3.5 ba
|
4500 sqft
MLS® 73560088Single Family Residence
Provided by MLS PIN - Pirani & Wile Group
Property at 666 Main Street #207, Winchester, MA 01890
1 / 27
Active Under Contract

$829,000

666 Main Street #207, Winchester, MA 01890

2 bds
|
2 ba
|
1170 sqft
MLS® 73559598Condominium
Better Homes and Gardens Real Estate - The Shanahan Group - Carolyn Vernaglia
Property at 7 Wainwright Road #113, Winchester, MA 01890
1 / 42
Active

$2,100,000

7 Wainwright Road #113, Winchester, MA 01890

4 bds
|
3.5 ba
|
3640 sqft
MLS® 73556476Condominium
Compass - Kim Covino & Co. Team
Property at 11 Viking Road, Winchester, MA 01890
1 / 36
Active

$3,600,000

11 Viking Road, Winchester, MA 01890

7 bds
|
7.5 ba
|
7429 sqft
MLS® 73556474Single Family Residence
Engel & Volkers Boston - Post Advisory Group
Property at 50 Holland Street, Winchester, MA 01890
1 / 42
Active

$1,549,000

50 Holland Street, Winchester, MA 01890

3 bds
|
2.5 ba
|
2640 sqft
MLS® 73556633Single Family Residence
Compass - Kim Covino & Co. Team
Property at 42 Wildwood Street, Winchester, MA 01890
1 / 42
Active
Open

$2,299,000

42 Wildwood Street, Winchester, MA 01890

7 bds
|
4.5 ba
|
4930 sqft
MLS® 73556122Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Carolyn Walsh
Property at 1 Town Way, Winchester, MA 01890
1 / 42
Active
Price

$1,794,000

1 Town Way, Winchester, MA 01890

3 bds
|
3.5 ba
|
3010 sqft
MLS® 73555777Single Family Residence
Compass - Vita Realty 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 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 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 Street #211, Winchester, MA 01890
1 / 42
Active
Price
Open

$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 47 Water Street, Winchester, MA 01890
1 / 30
Active

$950,000

47 Water Street, Winchester, MA 01890

3 bds
|
1.5 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
Price
Open

$710,000

247 Washington St #11, Winchester, MA 01890

3 bds
|
2.5 ba
|
1494 sqft
MLS® 73549877Condominium
Blue Ocean Realty, LLC - Heejeong Joo
Property at 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 Under Contract
Price

$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
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 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 / 38
Active
Price

$849,000

84 Oak Street, Winchester, MA 01890

4 bds
|
2 ba
|
2083 sqft
MLS® 73542597Single Family Residence
Charlesgate Realty Group LLC - John E. Magazzu
Page 1 of 2

Brokerage Information

Commonwealth Standard Realty Advisors

10 Lincoln St, Newton, MA, 02461

(781) 330-2264

Market Area Served

Newton, Brookline, Watertown, Belmont, Waltham, Wellesley, Wayland, Arlington, Natick, Needham, Stoneham, Wakefield, Lexington 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: 8/19/2026 at 8:28:00 PM

Andrea Forsythe

I'm Andrea Forsythe, a Newton, MA real estate agent specializing in new construction. With 13+ years developing homes, I guide buyers and sellers from search to keys.

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Equal Housing Opportunity. Information deemed reliable but not guaranteed.