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Homes for Sale in Winchester, MA

64 results

Property at 9 Priscilla Ln, Winchester, MA 01890
1 / 31
Active
New

$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 200 Swanton St #727, Winchester, MA 01890
1 / 16
Active
Open

$399,000

200 Swanton St #727, Winchester, MA 01890

1 bds
|
1 ba
|
613 sqft
MLS® 73579389Condominium
PRIVI Realty LLC - Alice Zheng
Property at 36 Elmwood Ave #11, Winchester, MA 01890
1 / 42
Active
Open

$1,350,000

36 Elmwood Ave #11, Winchester, MA 01890

2 bds
|
2.5 ba
|
1573 sqft
MLS® 73578288Condominium
Keller Williams Realty Boston-Metro | Back Bay - The Rasner Group
Property at 200 Swanton St #303, Winchester, MA 01890
1 / 24
Active
Open

$495,000

200 Swanton St #303, Winchester, MA 01890

2 bds
|
1 ba
|
822 sqft
MLS® 73578112Condominium
Redfin Corp. - Joseph Pollack
Property at 6 Reservoir Street, Winchester, MA 01890
1 / 2
Active

$1,080,000

6 Reservoir Street, Winchester, MA 01890

3 bds
|
1 ba
|
1382 sqft
MLS® 73578621Single Family Residence
HMW Real Estate, LLC - Dongjun Lou

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 7 Lakeview Terrace, Winchester, MA 01890
1 / 42
Active
Open

$2,600,000

7 Lakeview Terrace, Winchester, MA 01890

6 bds
|
3 ba
|
3534 sqft
MLS® 73578443Single Family Residence
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 11 Bonad Road, Winchester, MA 01890
1 / 42
Active Under Contract

$1,899,000

11 Bonad Road, Winchester, MA 01890

4 bds
|
3.5 ba
|
3257 sqft
MLS® 73577339Single Family Residence
Compass - Kim Covino & Co. Team
Property at 7 Sherman Place #7, Winchester, MA 01890
1 / 42
Active
Open

$1,495,000

7 Sherman Place #7, Winchester, MA 01890

4 bds
|
2.5 ba
|
2973 sqft
MLS® 73577640Condominium
Engel & Volkers Boston - John Dean
Property at 30 Willowdale Rd, Winchester, MA 01890
1 / 41
Active
Open

$3,200,000

30 Willowdale Rd, Winchester, MA 01890

8 bds
|
6.5 ba
|
5750 sqft
MLS® 73577116Single Family Residence
Leading Edge Real Estate - The Pallotta Group
Property at 189 Washington St #2, Winchester, MA 01890
1 / 38
Active
Open

$775,000

189 Washington St #2, Winchester, MA 01890

3 bds
|
2 ba
|
1643 sqft
MLS® 73575116Condominium
Compass - Kim Covino & Co. Team
Property at 465 Washington Street, Winchester, MA 01890
1 / 28
Active

$1,300,000

465 Washington Street, Winchester, MA 01890

4 bds
|
2.5 ba
|
2666 sqft
MLS® 73574928Single Family Residence
Leading Edge Real Estate - The Pallotta Group
Property at 143 Arlington Street, Winchester, MA 01890
1 / 42
Active

$1,599,000

143 Arlington Street, Winchester, MA 01890

5 bds
|
2 ba
|
2944 sqft
MLS® 73575069Single Family Residence
Compass - Kim Covino & Co. Team
Property at 258 Cross St, Winchester, MA 01890
1 / 34
Active
Open

$974,900

258 Cross St, Winchester, MA 01890

3 bds
|
2.5 ba
|
1719 sqft
MLS® 73575764Single Family Residence
Hartley Realty Group - Justin Blankenship
Property at 4 Dartmouth, Winchester, MA 01890
1 / 38
Active

$4,299,000

4 Dartmouth, Winchester, MA 01890

5 bds
|
5.5 ba
|
6526 sqft
MLS® 73574948Single Family Residence
Leading Edge Real Estate - The Pallotta Group
Property at 666 Main St #310, Winchester, MA 01890
1 / 41
Active

$769,000

666 Main St #310, Winchester, MA 01890

2 bds
|
2 ba
|
1170 sqft
MLS® 73575558Condominium
RE/MAX Bentley's - Darryl E. Brian
Property at 465 Washington Street #465, Winchester, MA 01890
1 / 28
Active

$1,300,000

465 Washington Street #465, Winchester, MA 01890

4 bds
|
2.5 ba
|
2666 sqft
MLS® 73574929Condominium
Leading Edge Real Estate - The Pallotta Group
Property at 117 Highland, Winchester, MA 01890
1 / 42
Active
Open

$1,650,000

117 Highland, Winchester, MA 01890

5 bds
|
3.5 ba
|
3722 sqft
MLS® 73573887Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Dara Singleton
Property at 11 Locke St, Winchester, MA 01890
1 / 25
Active Under Contract

$2,249,000

11 Locke St, Winchester, MA 01890

5 bds
|
3.5 ba
|
4368 sqft
MLS® 73574117Single Family Residence
Barrett Sotheby's International Realty - Lesley Smith
Property at 199 Washington Street #199, Winchester, MA 01890
1 / 42
Active

$975,000

199 Washington Street #199, Winchester, MA 01890

4 bds
|
3 ba
|
2475 sqft
MLS® 73573734Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 8 Priscilla Lane, Winchester, MA 01890
1 / 35
Active
Open

$2,995,000

8 Priscilla Lane, Winchester, MA 01890

5 bds
|
5.5 ba
|
6500 sqft
MLS® 73574330Single Family Residence
Rise Signature Homes - The Pezzano Group
Property at 253 Pond St, Winchester, MA 01890
1 / 40
Active Under Contract

$1,299,000

253 Pond St, Winchester, MA 01890

4 bds
|
1.5 ba
|
3307 sqft
MLS® 73574477Single Family Residence
Advisors Living - Winchester - Pirani & Wile Group
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
Open

$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
Open

$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 5 Willowdale Rd, Winchester, MA 01890
1 / 42
Active Under Contract

$1,679,900

5 Willowdale Rd, Winchester, MA 01890

3 bds
|
2 ba
|
2483 sqft
MLS® 73572791Single Family Residence
Coldwell Banker Realty - Lexington - Erica Carson
Property at 60 Lake St #E, Winchester, MA 01890
1 / 20
Active

$675,000

60 Lake St #E, Winchester, MA 01890

2 bds
|
1.5 ba
|
1190 sqft
MLS® 73572854Condominium
Coldwell Banker Realty - Boston - Shaundize Moosavizadeh
Property at 4 Churchill Road, Winchester, MA 01890
1 / 42
Active
Open

$1,699,000

4 Churchill Road, Winchester, MA 01890

3 bds
|
2 ba
|
2421 sqft
MLS® 73572661Single Family Residence
Compass - Kim Covino & Co. Team
Property at 26 N Gateway, Winchester, MA 01890
1 / 37
Active

$2,049,000

26 N Gateway, Winchester, MA 01890

4 bds
|
3.5 ba
|
3210 sqft
MLS® 73572687Single Family Residence
Advisors Living - Winchester - Pirani & Wile Group
Property at 24 Richardson St, Winchester, MA 01890
1 / 40
Active

$1,099,000

24 Richardson St, Winchester, MA 01890

4 bds
|
2.5 ba
|
2411 sqft
MLS® 73571480Single Family Residence
Keller Williams Realty Boston Northwest - Andersen Group Realty
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
Page 1 of 3

Brokerage Information

Commonwealth Standard Realty Advisors

10 Lincoln St, Newton, MA, 02461

(480) 540-2772

Market Area Served

Needham, Wellesley, Dedham, Natick, Westwood, Dover, Framingham, Wayland, Newton, Ashland, Sherborn 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: 9/18/2026 at 2:27:00 PM

Nick Biondo

I'm Nick Biondo, a Needham, MA real estate agent helping young and growing families find the right suburban home across MetroWest Boston — from first search to closing.

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