Single Family for Sale in Winchester MA - Homes of New Hampshire Realty

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: 13

Updated 13 Minutes Ago

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Photo of 11 Viking Road Winchester MA 01890

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11 Viking Road Winchester MA 01890

$3,600,000

Beds: 7

Baths: 7.5

Sq Ft: 7,429

Days on Market: 56

Updated 13 Minutes Ago

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Photo of 7 Hutchinson Road Winchester MA 01890

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7 Hutchinson Road Winchester MA 01890

$3,450,000

Beds: 6

Baths: 4.5

Sq Ft: 5,735

Days on Market: 44

Updated 13 Minutes Ago

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Photo of 9 Albamont Road Winchester MA 01890

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9 Albamont Road Winchester MA 01890

$3,200,000

Beds: 6

Baths: 5.5

Sq Ft: 6,100

Days on Market: 203

Updated 13 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: 44

Updated 13 Minutes Ago

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Photo of 30 Willowdale Rd Winchester MA 01890

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30 Willowdale Rd Winchester MA 01890

$3,200,000

Beds: 8

Baths: 6.5

Sq Ft: 5,750

Days on Market: 8

Updated 13 Minutes Ago

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Photo of 37 Mayflower Road Winchester MA 01890

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37 Mayflower Road Winchester MA 01890

$3,149,000

Beds: 7

Baths: 7.5

Sq Ft: 8,540

Days on Market: 15

Updated 13 Minutes Ago

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Photo of 8 Priscilla Lane Winchester MA 01890

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8 Priscilla Lane Winchester MA 01890

$2,995,000

Beds: 5

Baths: 5.5

Sq Ft: 6,500

Days on Market: 14

Updated 13 Minutes Ago

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Photo of 18 Middlesex St Winchester MA 01890

Open: Saturday 10:30 am - 12 pm

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18 Middlesex St Winchester MA 01890

$2,695,000

Beds: 4

Baths: 4.5

Sq Ft: 5,233

Days on Market: 133

Open: 9/26/26 10:30 AM - 12 PM

Updated 13 Minutes Ago

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Photo of 7 Lakeview Terrace Winchester MA 01890

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7 Lakeview Terrace Winchester MA 01890

$2,600,000

Beds: 6

Baths: 3

Sq Ft: 3,534

Days on Market: 7

Updated 13 Minutes Ago

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Photo of 54 Squire Road Winchester MA 01890

Price Reduced

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54 Squire Road Winchester MA 01890

$2,450,000

-$49,000

Beds: 4

Baths: 4.5

Sq Ft: 4,450

Days on Market: 43

Updated 13 Minutes Ago

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Photo of 9 Plymouth Rd Winchester MA 01890

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9 Plymouth Rd Winchester MA 01890

$2,400,000

Beds: 5

Baths: 3

Sq Ft: 4,071

Days on Market: 79

Updated 13 Minutes Ago

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Photo of 19 Hancock Street Winchester MA 01890

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19 Hancock Street Winchester MA 01890

$2,199,000

Beds: 4

Baths: 3.5

Sq Ft: 3,570

Days on Market: 15

Updated 13 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: 170

Updated 13 Minutes Ago

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Photo of 6 Ivy Circle Winchester MA 01890

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6 Ivy Circle Winchester MA 01890

$2,100,000

Beds: 6

Baths: 4

Sq Ft: 3,403

Days on Market: 146

Updated 13 Minutes Ago

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Photo of 26 N Gateway Winchester MA 01890

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26 N Gateway Winchester MA 01890

$2,049,000

Beds: 4

Baths: 3.5

Sq Ft: 3,210

Days on Market: 16

Updated 13 Minutes Ago

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85 High St Winchester MA 01890

$1,999,000

Beds: 4

Baths: 2.5

Sq Ft: 3,757

Days on Market: 35

Updated 13 Minutes Ago

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Photo of 79 Grove St Winchester MA 01890

Open: Saturday 10:30 am - 11:30 am

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79 Grove St Winchester MA 01890

$1,870,000

-$29,000

Beds: 5

Baths: 3.5

Sq Ft: 3,210

Days on Market: 78

Open: 9/26/26 10:30 AM - 11:30 AM, 9/27/26 12 PM - 1:30 PM

Updated 13 Minutes Ago

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Photo of 1 Overlook Way Winchester MA 01890

Open: Thursday 5 pm - 6:30 pm

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1 Overlook Way Winchester MA 01890

$1,850,000

Beds: 4

Baths: 2.5

Sq Ft: 3,092

Days on Market: 0

Open: 9/24/26 5 PM - 6:30 PM, 9/25/26 12 PM - 1:30 PM, 9/26/26 11 AM - 12:30 PM

Updated 13 Minutes Ago

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1 Town Way Winchester MA 01890

$1,749,000

Beds: 3

Baths: 3.5

Sq Ft: 3,010

Days on Market: 57

Updated 13 Minutes Ago

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Photo of 17 Churchill Rd Winchester MA 01890

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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: 15

Updated 13 Minutes Ago

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Photo of 4 Churchill Road Winchester MA 01890

Open: Friday 4 pm - 5:30 pm

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4 Churchill Road Winchester MA 01890

$1,699,000

Beds: 3

Baths: 2

Sq Ft: 2,421

Days on Market: 16

Open: 9/25/26 4 PM - 5:30 PM

Updated 13 Minutes Ago

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Photo of 117 Highland Winchester MA 01890

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117 Highland Winchester MA 01890

$1,650,000

Beds: 5

Baths: 3.5

Sq Ft: 3,722

Days on Market: 14

Updated 13 Minutes Ago

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Photo of 143 Arlington Street Winchester MA 01890

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143 Arlington Street Winchester MA 01890

$1,599,000

Beds: 5

Baths: 2

Sq Ft: 2,944

Days on Market: 13

Updated 13 Minutes Ago

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Photo of 50 Holland Street Winchester MA 01890

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50 Holland Street Winchester MA 01890

$1,549,000

Beds: 3

Baths: 2.5

Sq Ft: 2,640

Days on Market: 56

Updated 13 Minutes Ago

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Photo of 423 Washington St Winchester MA 01890

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423 Washington St Winchester MA 01890

$1,350,000

Beds: 4

Baths: 3

Sq Ft: 2,690

Days on Market: 90

Updated 13 Minutes Ago

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Photo of 110 Thornberry Road Winchester MA 01890

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110 Thornberry Road Winchester MA 01890

$1,329,000

Beds: 3

Baths: 2.5

Sq Ft: 2,459

Days on Market: 42

Updated 13 Minutes Ago

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Photo of 9 Priscilla Ln Winchester MA 01890

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9 Priscilla Ln Winchester MA 01890

$1,325,000

Beds: 4

Baths: 2

Sq Ft: 1,922

Days on Market: 5

Updated 13 Minutes Ago

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Photo of 465 Washington Street Winchester MA 01890

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465 Washington Street Winchester MA 01890

$1,300,000

Beds: 4

Baths: 2.5

Sq Ft: 2,666

Days on Market: 13

Updated 13 Minutes Ago

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Photo of 24 Richardson St Winchester MA 01890

Open: Saturday 1 pm - 2 pm

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24 Richardson St Winchester MA 01890

$1,099,000

Beds: 4

Baths: 2.5

Sq Ft: 2,411

Days on Market: 20

Open: 9/26/26 1 PM - 2 PM, 9/27/26 2 PM - 3 PM

Updated 13 Minutes Ago

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