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Homes for Sale in Winchester, MA

67 results

Property at 1 Overlook Way, Winchester, MA 01890
1 / 39
Active
New
Open

$1,850,000

1 Overlook Way, Winchester, MA 01890

4 bds
|
2.5 ba
|
3092 sqft
MLS® 73581571Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Lynne Russo
Property at 666 Main Street #217, Winchester, MA 01890
1 / 41
Active
New
Open

$700,000

666 Main Street #217, Winchester, MA 01890

2 bds
|
2 ba
|
1240 sqft
MLS® 73581469Condominium
Berkshire Hathaway HomeServices Commonwealth Real Estate - Elizabeth Darby
Property at 23 Stone Ave., Winchester, MA 01890
1 / 35
Active
New

$1,000,000

23 Stone Ave., Winchester, MA 01890

3 bds
|
1 ba
|
1908 sqft
MLS® 73581744Single Family Residence
Better Homes and Gardens Real Estate - The Shanahan Group - Dara Singleton
Property at 7 Wainwright Rd. ##47, Winchester, MA 01890
1 / 37
Active
New

$1,295,000

7 Wainwright Rd. ##47, Winchester, MA 01890

3 bds
|
3 ba
|
2145 sqft
MLS® 73580454Condominium
Better Homes and Gardens Real Estate - The Shanahan Group - Felicity F. Tuttle
Property at 200 Swanton St #T14, Winchester, MA 01890
1 / 26
Active
New

$349,900

200 Swanton St #T14, Winchester, MA 01890

1 bds
|
1 ba
|
602 sqft
MLS® 73580409Condominium
The Synergy Group - The Synergy Group

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 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 Under Contract

$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

$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
Property at 7 Lakeview Terrace, Winchester, MA 01890
1 / 42
Active

$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

$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

$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

$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

$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

$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 Under Contract

$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

$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

$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 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
Page 1 of 3

Brokerage Information

eXp Realty

165 Thorndike Street, Lowell, MA, 01852

(978) 267-7409

Market Area Served

Boston, Worcester, Waltham, Lowell, Norwood, Burlington, Framingham, Fitchburg, Newton 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: 9/23/2026 at 7:56:00 PM

Sam Al-Harbi

I'm Sam Al-Harbi, a Boston investor-Realtor who owns 3 buildings and 8 doors. I help buyers, sellers and investors build multifamily and commercial portfolios across Greater Boston.

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  • 165 Thorndike Street, Lowell, MA, 01852
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Equal Housing Opportunity. Information deemed reliable but not guaranteed.