Single Family for Sale in Winchester MA

Photo of 4 Dartmouth St Winchester MA 01890

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4 Dartmouth St Winchester MA 01890

$4,699,000

Beds: 5

Baths: 5.5

Sq Ft: 6,526

Days on Market: 17

Updated 14 Minutes Ago

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Photo of 9 Lakeview Terrace Winchester MA 01890

Under Contract

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9 Lakeview Terrace Winchester MA 01890

$3,750,000

Beds: 6

Baths: 3.5

Sq Ft: 4,484

Days on Market: 282

Updated 14 Minutes Ago

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Photo of 40 Foxcroft Rd Winchester MA 01890

Open: Sunday 12 pm - 1:30 pm

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40 Foxcroft Rd Winchester MA 01890

$3,750,000

Beds: 6

Baths: 4.5

Sq Ft: 6,460

Days on Market: 10

Open: 3/22/26 12 PM - 1:30 PM

Updated 14 Minutes Ago

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Photo of 2 Everett Ave Winchester MA 01890

New Listing

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2 Everett Ave Winchester MA 01890

$3,747,000

Beds: 7

Baths: 4.5

Sq Ft: 7,043

Days on Market: 3

Updated 14 Minutes Ago

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Photo of 20 Amberwood Dr Winchester MA 01890

Open: Sunday 1:30 pm - 2:30 pm

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20 Amberwood Dr Winchester MA 01890

$3,600,000

Beds: 6

Baths: 7

Sq Ft: 8,866

Days on Market: 202

Open: 3/22/26 1:30 PM - 2:30 PM

Updated 14 Minutes Ago

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Photo of 37 Mayflower Road Winchester MA 01890

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37 Mayflower Road Winchester MA 01890

$3,537,000

Beds: 7

Baths: 7.5

Sq Ft: 8,540

Days on Market: 41

Updated 14 Minutes Ago

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Photo of 54 Johnson Rd Winchester MA 01890

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54 Johnson Rd Winchester MA 01890

$3,499,000

Beds: 5

Baths: 7.5

Sq Ft: 6,899

Days on Market: 46

Updated 14 Minutes Ago

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Photo of 15 Mayflower Rd Winchester MA 01890

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15 Mayflower Rd Winchester MA 01890

$3,425,000

Beds: 7

Baths: 7.5

Sq Ft: 7,226

Days on Market: 46

Updated 14 Minutes Ago

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Photo of 9 Albamont Road Winchester MA 01890

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9 Albamont Road Winchester MA 01890

$3,400,000

Beds: 6

Baths: 5.5

Sq Ft: 6,100

Days on Market: 18

Updated 14 Minutes Ago

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Photo of 25 Myopia Road Winchester MA 01890

Open: Sunday 10:45 am - 12:15 pm

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25 Myopia Road Winchester MA 01890

$3,390,000

Beds: 4

Baths: 3.5

Sq Ft: 4,847

Days on Market: 55

Open: 3/22/26 10:45 AM - 12:15 PM

Updated 14 Minutes Ago

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Photo of 10 Dartmouth Street Winchester MA 01890

Open: Sunday 11 am - 12:30 pm

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10 Dartmouth Street Winchester MA 01890

$3,299,000

Beds: 5

Baths: 3

Sq Ft: 4,028

Days on Market: 4

Open: 3/22/26 11 AM - 12:30 PM

Updated 14 Minutes Ago

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Photo of 27 Everett Ave Winchester MA 01890

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27 Everett Ave Winchester MA 01890

$3,290,000

Beds: 6

Baths: 5.5

Sq Ft: 7,431

Days on Market: 66

Updated 14 Minutes Ago

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Photo of 39 Town Way Winchester MA 01890

Under Contract

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39 Town Way Winchester MA 01890

$3,199,000

Beds: 6

Baths: 6

Sq Ft: 5,709

Days on Market: 163

Updated 14 Minutes Ago

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Photo of 45 Bacon Street Winchester MA 01890

Open: Sunday 1 pm - 2:30 pm

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45 Bacon Street Winchester MA 01890

$2,965,000

Beds: 7

Baths: 7

Sq Ft: 7,043

Days on Market: 25

Open: 3/22/26 1 PM - 2:30 PM

Updated 14 Minutes Ago

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Photo of 19 Town Way Winchester MA 01890

Under Contract

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19 Town Way Winchester MA 01890

$2,899,000

Beds: 5

Baths: 5.5

Sq Ft: 5,257

Days on Market: 124

Updated 14 Minutes Ago

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Photo of 53 Winford Way Winchester MA 01890

Open: Sunday 1:30 pm - 2:30 pm

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53 Winford Way Winchester MA 01890

$2,799,000

Beds: 5

Baths: 4

Sq Ft: 5,083

Days on Market: 20

Open: 3/22/26 1:30 PM - 2:30 PM

Updated 14 Minutes Ago

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Photo of 2 Priscilla Lane Winchester MA 01890

Under Contract

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2 Priscilla Lane Winchester MA 01890

$2,699,000

Beds: 4

Baths: 3.5

Sq Ft: 4,255

Days on Market: 11

Updated 14 Minutes Ago

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Photo of 107 Cambridge Street Winchester MA 01890

Under Contract

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107 Cambridge Street Winchester MA 01890

$2,499,000

Beds: 6

Baths: 4.5

Sq Ft: 5,824

Days on Market: 286

Updated 14 Minutes Ago

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Photo of 10 Viking Rd Winchester MA 01890

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10 Viking Rd Winchester MA 01890

$2,499,000

Beds: 4

Baths: 4

Sq Ft: 5,674

Days on Market: 72

Updated 14 Minutes Ago

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Photo of 89 Wildwood St Winchester MA 01890

Under Contract

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89 Wildwood St Winchester MA 01890

$2,299,000

Beds: 7

Baths: 5.5

Sq Ft: 4,929

Days on Market: 128

Updated 14 Minutes Ago

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Under Contract

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12 Yale St Winchester MA 01890

$2,299,000

Beds: 4

Baths: 2.5

Sq Ft: 3,283

Days on Market: 24

Updated 14 Minutes Ago

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Photo of 61 Grove Street Winchester MA 01890

Under Contract

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61 Grove Street Winchester MA 01890

$2,199,000

Beds: 5

Baths: 4.5

Sq Ft: 4,798

Days on Market: 59

Updated 14 Minutes Ago

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Open: Sunday 12 pm - 1:30 pm

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6 Ivy Cir Winchester MA 01890

$2,150,000

-$100,000

Beds: 6

Baths: 4

Sq Ft: 3,728

Days on Market: 166

Open: 3/22/26 12 PM - 1:30 PM

Updated 14 Minutes Ago

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Photo of 15 Wildwood Street Winchester MA 01890

Open: Sunday 11 am - 12:30 pm

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15 Wildwood Street Winchester MA 01890

$2,100,000

Beds: 6

Baths: 2.5

Sq Ft: 4,104

Days on Market: 4

Open: 3/22/26 11 AM - 12:30 PM

Updated 14 Minutes Ago

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Photo of 4 Leslie Road Winchester MA 01890

Under Contract

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4 Leslie Road Winchester MA 01890

$1,999,900

Beds: 5

Baths: 3.5

Sq Ft: 2,860

Days on Market: 11

Updated 14 Minutes Ago

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Photo of 237 Swanton Street Winchester MA 01890

Open: Sunday 11:30 am - 12:30 pm

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237 Swanton Street Winchester MA 01890

$1,945,000

-$50,000

Beds: 5

Baths: 4

Sq Ft: 4,334

Days on Market: 108

Open: 3/22/26 11:30 AM - 12:30 PM

Updated 14 Minutes Ago

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1 Town Way Winchester MA 01890

$1,899,000

Beds: 3

Baths: 3.5

Sq Ft: 3,010

Days on Market: 74

Updated 14 Minutes Ago

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Photo of 20 Grove Pl Winchester MA 01890

Under Contract

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20 Grove Pl Winchester MA 01890

$1,869,000

Beds: 5

Baths: 3.5

Sq Ft: 3,294

Days on Market: 125

Updated 14 Minutes Ago

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Photo of 35 Hollywood Rd Winchester MA 01890

Price Reduced

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35 Hollywood Rd Winchester MA 01890

$1,799,900

-$88,100

Beds: 4

Baths: 4.5

Sq Ft: 3,906

Days on Market: 11

Updated 14 Minutes Ago

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Photo of 58 Jefferson Road Winchester MA 01890

Open: Sunday 11 am - 12:30 pm

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58 Jefferson Road Winchester MA 01890

$1,799,000

Beds: 4

Baths: 2.5

Sq Ft: 2,910

Days on Market: 3

Open: 3/22/26 11 AM - 12:30 PM

Updated 14 Minutes Ago

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