Homes and Real Estate for Sale in Winthrop MA

Photo of 155-165 Shirley St Winthrop MA 02152

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155-165 Shirley St Winthrop MA 02152

$4,000,000

Beds:

Baths:

Sq Ft: 10,386

Days on Market: 54

Updated 8 Minutes Ago

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Photo of 63-69 Putnam St Winthrop MA 02152

New Listing

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63-69 Putnam St Winthrop MA 02152

$2,460,000

Beds:

Baths:

Sq Ft:

Days on Market: 3

Updated 8 Minutes Ago

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Photo of 191 Cottage Park Road Winthrop MA 02152

Under Contract

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191 Cottage Park Road Winthrop MA 02152

$1,799,000

Beds: 6

Baths: 3.5

Sq Ft: 4,455

Days on Market: 205

Updated 8 Minutes Ago

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Photo of 201 Cliff Avenue Winthrop MA 02152

Under Contract

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201 Cliff Avenue Winthrop MA 02152

$1,785,000

Beds: 8

Baths: 6.5

Sq Ft: 5,362

Days on Market: 80

Updated 8 Minutes Ago

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Photo of 304 Shirley Street Winthrop MA 02152

New Listing

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304 Shirley Street Winthrop MA 02152

$1,650,000

Beds: 6

Baths: 6

Sq Ft: 4,122

Days on Market: 7

Updated 8 Minutes Ago

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Photo of 142 Washington Ave Winthrop MA 02152

Under Contract

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142 Washington Ave Winthrop MA 02152

$1,599,999

Beds: 6

Baths: 3

Sq Ft: 4,754

Days on Market: 29

Updated 8 Minutes Ago

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Photo of 129 Strandway Winthrop MA 02152

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129 Strandway Winthrop MA 02152

$1,324,900

Beds: 4

Baths: 3

Sq Ft: 2,640

Days on Market: 140

Updated 8 Minutes Ago

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Photo of 37 Trident Ave Winthrop MA 02152

Under Contract

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37 Trident Ave Winthrop MA 02152

$1,300,000

Beds: 8

Baths: 3

Sq Ft: 3,708

Days on Market: 120

Updated 8 Minutes Ago

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Photo of 43-45 Ocean Avenue Winthrop MA 02152

Under Contract

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43-45 Ocean Avenue Winthrop MA 02152

$1,300,000

Beds: 8

Baths: 4

Sq Ft: 5,124

Days on Market: 53

Updated 8 Minutes Ago

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Photo of 10-12 Charles St Winthrop MA 02152

Under Contract

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10-12 Charles St Winthrop MA 02152

$1,300,000

Beds: 7

Baths: 4

Sq Ft: 3,688

Days on Market: 48

Updated 8 Minutes Ago

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Photo of 47 Bellevue Ave Winthrop MA 02152

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47 Bellevue Ave Winthrop MA 02152

$1,280,000

Beds: 6

Baths: 3.5

Sq Ft: 3,400

Days on Market: 109

Updated 8 Minutes Ago

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Photo of 22 Upland Road Winthrop MA 02152

Under Contract

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22 Upland Road Winthrop MA 02152

$1,250,000

Beds: 6

Baths: 3.5

Sq Ft: 4,062

Days on Market: 53

Updated 8 Minutes Ago

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Photo of 66 Lowell Road Winthrop MA 02152

Under Contract

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66 Lowell Road Winthrop MA 02152

$1,150,000

Beds: 6

Baths: 2.5

Sq Ft: 3,458

Days on Market: 201

Updated 8 Minutes Ago

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Photo of 1001 Shirley #1 Winthrop MA 02152

Open: Saturday 11 am - 1 pm

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1001 Shirley #1 Winthrop MA 02152

$1,125,000

Beds: 2

Baths: 2.5

Sq Ft: 1,978

Days on Market: 169

Open: 3/28/26 11 AM - 1 PM

Updated 8 Minutes Ago

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Photo of 1001 Shirley #5 Winthrop MA 02152

Open: Saturday 11 am - 1 pm

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1001 Shirley #5 Winthrop MA 02152

$1,050,000

Beds: 2

Baths: 2.5

Sq Ft: 1,785

Days on Market: 77

Open: 3/28/26 11 AM - 1 PM

Updated 8 Minutes Ago

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Open: Saturday 11 am - 12:30 pm

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24 photos

11 Pearl Ave Winthrop MA 02152

$1,050,000

Beds: 11

Baths: 3

Sq Ft: 4,032

Days on Market: 1

Open: 3/28/26 11 AM - 12:30 PM, 3/29/26 11 AM - 12:30 PM

Updated 8 Minutes Ago

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Photo of 550 Pleasant St #506 Winthrop MA 02152

Under Contract

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550 Pleasant St #506 Winthrop MA 02152

$1,030,000

Beds: 2

Baths: 2

Sq Ft: 1,975

Days on Market: 127

Updated 8 Minutes Ago

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Photo of 50-52 Wilshire St Winthrop MA 02152

Under Contract

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50-52 Wilshire St Winthrop MA 02152

$990,000

Beds: 6

Baths: 2

Sq Ft: 2,212

Days on Market: 28

Updated 8 Minutes Ago

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Photo of 170 Cottage Park Rd Winthrop MA 02152

Under Contract

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170 Cottage Park Rd Winthrop MA 02152

$989,000

Beds: 7

Baths: 4

Sq Ft: 3,800

Days on Market: 2056

Updated 8 Minutes Ago

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Photo of 1001 Shirley #3 Winthrop MA 02152

Open: Saturday 11 am - 1 pm

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21 photos

1001 Shirley #3 Winthrop MA 02152

$939,900

Beds: 2

Baths: 2.5

Sq Ft: 1,551

Days on Market: 169

Open: 3/28/26 11 AM - 1 PM

Updated 8 Minutes Ago

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Photo of 876 Shirley #1 Winthrop MA 02152

Price Reduced

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876 Shirley #1 Winthrop MA 02152

$829,999

-$10,000

Beds: 4

Baths: 2

Sq Ft: 2,000

Days on Market: 63

Updated 8 Minutes Ago

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42 photos

19 Moore St Winthrop MA 02152

$829,974

Beds: 5

Baths: 2.5

Sq Ft: 2,212

Days on Market: 16

Updated 8 Minutes Ago

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Photo of 56 Main Street Winthrop MA 02152

Under Contract

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56 Main Street Winthrop MA 02152

$799,900

Beds: 4

Baths: 2

Sq Ft: 2,103

Days on Market: 111

Updated 8 Minutes Ago

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Photo of 426 Winthrop St Winthrop MA 02152

Under Contract

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426 Winthrop St Winthrop MA 02152

$749,900

Beds: 5

Baths: 2.5

Sq Ft: 2,394

Days on Market: 1869

Updated 8 Minutes Ago

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Photo of 140 Shirley Street #310 Winthrop MA 02152

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140 Shirley Street #310 Winthrop MA 02152

$749,900

Beds: 2

Baths: 2

Sq Ft: 1,113

Days on Market: 36

Updated 8 Minutes Ago

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Photo of 148 Winthrop Shore Dr #4 Winthrop MA 02152

Under Contract

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148 Winthrop Shore Dr #4 Winthrop MA 02152

$729,000

Beds: 2

Baths: 2

Sq Ft: 1,165

Days on Market: 290

Updated 8 Minutes Ago

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Photo of 14 Pleasant Park Road Winthrop MA 02152

Under Contract

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14 Pleasant Park Road Winthrop MA 02152

$719,900

Beds: 4

Baths: 1

Sq Ft: 1,964

Days on Market: 182

Updated 8 Minutes Ago

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Photo of 960 Shirley St Winthrop MA 02152

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

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38 photos

960 Shirley St Winthrop MA 02152

$695,000

-$10,000

Beds: 3

Baths: 1.5

Sq Ft: 1,764

Days on Market: 136

Open: 3/28/26 12:30 PM - 1:30 PM

Updated 8 Minutes Ago

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Photo of 51 Harbor View Ave #3 Winthrop MA 02152

Open: Sunday 12 pm - 1:30 pm

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51 Harbor View Ave #3 Winthrop MA 02152

$689,000

-$11,000

Beds: 2

Baths: 1

Sq Ft: 1,304

Days on Market: 29

Open: 3/29/26 12 PM - 1:30 PM

Updated 8 Minutes Ago

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Photo of 51 Harbor View Ave #2 Winthrop MA 02152

Open: Sunday 12 pm - 1:30 pm

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30 photos

51 Harbor View Ave #2 Winthrop MA 02152

$659,000

-$16,000

Beds: 2

Baths: 1

Sq Ft: 1,220

Days on Market: 29

Open: 3/29/26 12 PM - 1:30 PM

Updated 8 Minutes Ago

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