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Houses for Sale in Winchester, MA – Page 2

47 results

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
Property at 1 Plymouth Rd., Winchester, MA 01890
1 / 28
Active

$3,299,000

1 Plymouth Rd., Winchester, MA 01890

7 bds
|
7.5 ba
|
7226 sqft
MLS® 73585058Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 85 High St, Winchester, MA 01890
1 / 38
Active
Price

$1,899,000

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 257 Cross Street, Winchester, MA 01890
1 / 40
Active

$1,050,000

257 Cross Street, Winchester, MA 01890

5 bds
|
2.5 ba
|
2801 sqft
MLS® 73571418Single Family Residence
Compass - Kim Covino & Co. Team
Property at 96 Loring Ave, Winchester, MA 01890
1 / 29
Active
Price

$919,999

96 Loring Ave, Winchester, MA 01890

4 bds
|
2 ba
|
2326 sqft
MLS® 73561829Single Family Residence
StartPoint Realty - Jeremy Smith

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 9 Priscilla Ln, Winchester, MA 01890
1 / 31
Active

$1,325,000

9 Priscilla Ln, Winchester, MA 01890

4 bds
|
2 ba
|
1922 sqft
MLS® 73579538Single Family Residence
Compass - Robert Del Greco
Property at 6 Ivy Circle, Winchester, MA 01890
1 / 36
Active

$2,100,000

6 Ivy Circle, Winchester, MA 01890

6 bds
|
4 ba
|
3403 sqft
MLS® 73510713Single Family Residence
Engel & Volkers Boston - Post Advisory Group
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 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 17 Russell Rd, Winchester, MA 01890
1 / 25
Active

$1,098,000

17 Russell Rd, Winchester, MA 01890

3 bds
|
1.5 ba
|
1657 sqft
MLS® 73566405Single Family Residence
Kwan Realty Inc. - Tsz Mui Kwan
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 30 Willowdale Rd, Winchester, MA 01890
1 / 41
Active

$3,200,000

30 Willowdale Rd, Winchester, MA 01890

8 bds
|
6.5 ba
|
5750 sqft
MLS® 73577116Single Family Residence
Gibson Sotheby's International Realty - The Pallotta Group
Property at 47 Water Street, Winchester, MA 01890
1 / 30
Active
Price

$899,000

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 37 Mayflower Road, Winchester, MA 01890
1 / 42
Active

$3,149,000

37 Mayflower Road, Winchester, MA 01890

7 bds
|
7.5 ba
|
8540 sqft
MLS® 73573670Single Family Residence
Compass - Kim Covino & Co. Team
Property at 17 Churchill Rd, Winchester, MA 01890
1 / 37
Active

$1,749,000

17 Churchill Rd, Winchester, MA 01890

5 bds
|
3.5 ba
|
3508 sqft
MLS® 73572890Single Family Residence
Coldwell Banker Realty - Lexington - Domingo Medina
Property at 19 Hancock Street, Winchester, MA 01890
1 / 40
Active

$2,199,000

19 Hancock Street, Winchester, MA 01890

4 bds
|
3.5 ba
|
3570 sqft
MLS® 73572955Single Family Residence
Compass - Vita Realty Group
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
Page 2 of 2

Brokerage Information

Gibson Sotheby's International Realty

526B Boston Post Road, Sudbury, MA, 01776

(207) 939-1067

License #9630186-RE-S

Market Area Served

Concord, Carlisle, Lexington, Newton, Wellesley, Weston, Somerville, Belmont, Cambridge, Bedford, Lincoln, Arlington, Sudbury 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.

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Amanda Allen Nurse

I'm Amanda Allen Nurse, a Concord, MA real estate agent with Gibson Sotheby's, guiding move-up families and home sellers across MetroWest from first search to closing.

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Gibson Sotheby's International Realty

© 2026 Amanda Allen Nurse. All rights reserved.
License #9630186-RE-S. Equal Housing Opportunity. Information deemed reliable but not guaranteed.

Service Areas

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  • Belmont, MA
  • Cambridge, MA
  • Arlington, MA
  • Weston, MA
  • Newton, MA
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  • Sudbury

    526B Boston Post Road

    Sudbury, MA 01776

    9784438484