Colonial for Sale in Winchester MA - Classic Homes Realty

Photo of 9 Lakeview Terrace Winchester MA 01890

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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: 295

Updated 3 Minutes Ago

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Photo of 40 Foxcroft Rd Winchester MA 01890

Open: Saturday 11:30 am - 1 pm

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40 Foxcroft Rd Winchester MA 01890

$3,650,000

-$100,000

Beds: 6

Baths: 4.5

Sq Ft: 6,460

Days on Market: 23

Open: 4/4/26 11:30 AM - 1 PM

Updated 3 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: 54

Updated 3 Minutes Ago

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Photo of 54 Johnson Rd Winchester MA 01890

Open: Saturday 11 am - 12 pm

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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: 59

Open: 4/4/26 11 AM - 12 PM

Updated 3 Minutes Ago

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Photo of 15 Mayflower Rd Winchester MA 01890

Open: Saturday 12 pm - 1:30 pm

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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: 59

Open: 4/4/26 12 PM - 1:30 PM

Updated 3 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: 31

Updated 3 Minutes Ago

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Photo of 10 Dartmouth Street Winchester MA 01890

Open: Saturday 12:30 pm - 1:30 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: 17

Open: 4/4/26 12:30 PM - 1:30 PM

Updated 3 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: 79

Updated 3 Minutes Ago

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Photo of 39 Town Way Winchester MA 01890

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39 Town Way Winchester MA 01890

$3,199,000

Beds: 6

Baths: 6

Sq Ft: 5,709

Days on Market: 176

Updated 3 Minutes Ago

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Photo of 45 Bacon Street Winchester MA 01890

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45 Bacon Street Winchester MA 01890

$2,965,000

Beds: 7

Baths: 7

Sq Ft: 7,043

Days on Market: 38

Updated 3 Minutes Ago

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Photo of 53 Winford Way Winchester MA 01890

Open: Saturday 12 pm - 1 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: 33

Open: 4/4/26 12 PM - 1 PM

Updated 3 Minutes Ago

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Photo of 56 Yale Street Winchester MA 01890

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56 Yale Street Winchester MA 01890

$2,795,000

Beds: 5

Baths: 3.5

Sq Ft: 4,792

Days on Market: 10

Updated 3 Minutes Ago

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Photo of 2 Priscilla Lane Winchester MA 01890

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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: 24

Updated 3 Minutes Ago

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Photo of 89 Wildwood St Winchester MA 01890

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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: 141

Updated 3 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: 37

Updated 3 Minutes Ago

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Photo of 4 Leslie Road Winchester MA 01890

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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: 24

Updated 3 Minutes Ago

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Photo of 237 Swanton Street Winchester MA 01890

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

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237 Swanton Street Winchester MA 01890

$1,945,000

Beds: 5

Baths: 4

Sq Ft: 4,334

Days on Market: 121

Open: 4/4/26 11:30 AM - 12:30 PM

Updated 3 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: 87

Updated 3 Minutes Ago

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Photo of 35 Hollywood Rd Winchester MA 01890

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35 Hollywood Rd Winchester MA 01890

$1,799,900

Beds: 4

Baths: 4.5

Sq Ft: 3,906

Days on Market: 24

Updated 3 Minutes Ago

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Photo of 58 Jefferson Road Winchester MA 01890

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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: 16

Updated 3 Minutes Ago

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Photo of 114 Johnson Rd Winchester MA 01890

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114 Johnson Rd Winchester MA 01890

$1,795,000

Beds: 3

Baths: 3

Sq Ft: 3,182

Days on Market: 44

Updated 3 Minutes Ago

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Photo of 12 Wincrest Drive Winchester MA 01890

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12 Wincrest Drive Winchester MA 01890

$1,750,000

Beds: 6

Baths: 4.5

Sq Ft: 3,833

Days on Market: 9

Updated 3 Minutes Ago

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Photo of 34 Robinhood Road Winchester MA 01890

Open: Saturday 1 pm - 2 pm

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34 Robinhood Road Winchester MA 01890

$1,524,000

-$75,000

Beds: 4

Baths: 2.5

Sq Ft: 3,380

Days on Market: 20

Open: 4/4/26 1 PM - 2 PM

Updated 3 Minutes Ago

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Photo of 65 High Street Winchester MA 01890

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65 High Street Winchester MA 01890

$1,499,999

Beds: 6

Baths: 3

Sq Ft: 2,658

Days on Market: 24

Updated 3 Minutes Ago

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Photo of 6 Marchant Road Winchester MA 01890

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6 Marchant Road Winchester MA 01890

$1,350,000

Beds: 3

Baths: 2.5

Sq Ft: 2,153

Days on Market: 60

Updated 3 Minutes Ago

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Photo of 259 Washington Street Winchester MA 01890

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259 Washington Street Winchester MA 01890

$1,349,900

Beds: 4

Baths: 3.5

Sq Ft: 2,590

Days on Market: 38

Updated 3 Minutes Ago

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Photo of 155 Highland Ave Winchester MA 01890

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155 Highland Ave Winchester MA 01890

$1,339,000

Beds: 5

Baths: 2.5

Sq Ft: 1,965

Days on Market: 236

Updated 3 Minutes Ago

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Photo of 40 Pickering St Winchester MA 01890

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40 Pickering St Winchester MA 01890

$1,249,900

Beds: 4

Baths: 2.5

Sq Ft: 2,454

Days on Market: 25

Updated 3 Minutes Ago

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Photo of 53 Lake Street Winchester MA 01890

Under Contract

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53 Lake Street Winchester MA 01890

$1,199,000

Beds: 3

Baths: 2.5

Sq Ft: 2,235

Days on Market: 18

Updated 3 Minutes Ago

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Photo of 76 Woodside Road Winchester MA 01890

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76 Woodside Road Winchester MA 01890

$999,000

Beds: 4

Baths: 2

Sq Ft: 1,552

Days on Market: 9

Updated 3 Minutes Ago

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