Single Family 5 Bedroom for Sale in Winchester MA

Photo of 4 Dartmouth Winchester MA 01890

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4 Dartmouth Winchester MA 01890

$4,299,000

Beds: 5

Baths: 5.5

Sq Ft: 6,526

Days on Market: 37

Updated 6 Minutes Ago

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Photo of 18 Ridge St Winchester MA 01890

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18 Ridge St Winchester MA 01890

$3,200,000

Beds: 5

Baths: 5.5

Sq Ft: 5,295

Days on Market: 68

Updated 6 Minutes Ago

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Photo of 9 Plymouth Rd Winchester MA 01890

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9 Plymouth Rd Winchester MA 01890

$2,250,000

Beds: 5

Baths: 3

Sq Ft: 4,071

Days on Market: 103

Updated 6 Minutes Ago

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Photo of 276 High Street Winchester MA 01890

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276 High Street Winchester MA 01890

$2,195,000

Beds: 5

Baths: 3.5

Sq Ft: 5,006

Days on Market: 194

Updated 6 Minutes Ago

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Photo of 21 Amberwood Dr Winchester MA 01890

Open: Saturday 11 am - 12:30 pm

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21 Amberwood Dr Winchester MA 01890

$2,049,000

Beds: 5

Baths: 3.5

Sq Ft: 4,063

Days on Market: 10

Open: 10/17/26 11 AM - 12:30 PM, 10/18/26 1 PM - 2:30 PM

Updated 6 Minutes Ago

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Photo of 26 Mayflower Road Winchester MA 01890

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26 Mayflower Road Winchester MA 01890

$1,950,000

Beds: 5

Baths: 4

Sq Ft: 3,371

Days on Market: 18

Updated 6 Minutes Ago

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Photo of 17 Churchill Rd Winchester MA 01890

Open: Sunday 11:30 am - 1 pm

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17 Churchill Rd Winchester MA 01890

$1,749,000

Beds: 5

Baths: 3.5

Sq Ft: 3,508

Days on Market: 39

Open: 10/18/26 11:30 AM - 1 PM

Updated 6 Minutes Ago

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Photo of 117 Highland Winchester MA 01890

Open: Saturday 1 pm - 2 pm

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117 Highland Winchester MA 01890

$1,650,000

Beds: 5

Baths: 3.5

Sq Ft: 3,722

Days on Market: 38

Open: 10/17/26 1 PM - 2 PM

Updated 6 Minutes Ago

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Photo of 15 Lloyd Street Winchester MA 01890

Open: Saturday 10:30 am - 12 pm

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15 Lloyd Street Winchester MA 01890

$1,399,000

Beds: 5

Baths: 1.5

Sq Ft: 2,071

Days on Market: 8

Open: 10/17/26 10:30 AM - 12 PM, 10/18/26 12:30 PM - 2 PM

Updated 6 Minutes Ago

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Photo of 257 Cross Street Winchester MA 01890

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257 Cross Street Winchester MA 01890

$1,050,000

Beds: 5

Baths: 2.5

Sq Ft: 2,801

Days on Market: 45

Updated 6 Minutes Ago

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Photo of 10 Bellevue Avenue Winchester MA 01890

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10 Bellevue Avenue Winchester MA 01890

$11,500 / mo

Beds: 5

Baths: 3

Sq Ft: 4,132

Days on Market: 46

Updated 6 Minutes Ago

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Photo of 79 Bacon St #79 Winchester MA 01890

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79 Bacon St #79 Winchester MA 01890

$4,850 / mo

Beds: 5

Baths: 2

Sq Ft: 2,174

Days on Market: 72

Updated 6 Minutes Ago

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