Condo/Villa 2 Bedroom for Sale in Winthrop MA

Photo of 1001 Shirley #2 Winthrop MA 02152

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1001 Shirley #2 Winthrop MA 02152

$949,900

Beds: 2

Baths: 2.5

Sq Ft: 1,806

Days on Market: 65

Updated 2 Minutes Ago

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Photo of 1001 Shirley #3 Winthrop MA 02152

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1001 Shirley #3 Winthrop MA 02152

$849,900

Beds: 2

Baths: 2.5

Sq Ft: 1,551

Days on Market: 58

Updated 2 Minutes Ago

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Photo of 1 Seal Harbor #PH16 Winthrop MA 02152

Open: Sunday 1 pm - 2:30 pm

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1 Seal Harbor #PH16 Winthrop MA 02152

$775,000

-$24,000

Beds: 2

Baths: 2

Sq Ft: 1,417

Days on Market: 31

Open: 7/12/26 1 PM - 2:30 PM

Updated 2 Minutes Ago

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Photo of 21 Hutchinson #1 Winthrop MA 02152

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21 Hutchinson #1 Winthrop MA 02152

$749,000

Beds: 2

Baths: 2.5

Sq Ft: 1,800

Days on Market: 29

Updated 2 Minutes Ago

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Photo of 140 Shirley Street #250 Winthrop MA 02152

Open: Saturday 12 pm - 1:30 pm

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140 Shirley Street #250 Winthrop MA 02152

$725,000

Beds: 2

Baths: 2

Sq Ft: 1,113

Days on Market: 14

Open: 7/11/26 12 PM - 1:30 PM, 7/12/26 12 PM - 1:30 PM

Updated 2 Minutes Ago

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Photo of 550 Pleasant Street #411 Winthrop MA 02152

Under Contract

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550 Pleasant Street #411 Winthrop MA 02152

$689,000

Beds: 2

Baths: 2

Sq Ft: 1,183

Days on Market: 29

Updated 2 Minutes Ago

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Photo of 21 Hutchinson Street #B Winthrop MA 02152

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21 Hutchinson Street #B Winthrop MA 02152

$675,000

Beds: 2

Baths: 2.5

Sq Ft: 1,360

Days on Market: 14

Updated 2 Minutes Ago

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Photo of 3 Seal Harbor Road #342 Winthrop MA 02152

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3 Seal Harbor Road #342 Winthrop MA 02152

$649,000

Beds: 2

Baths: 2

Sq Ft: 1,302

Days on Market: 78

Updated 2 Minutes Ago

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Photo of 1 Seal Harbor Rd #815 Winthrop MA 02152

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1 Seal Harbor Rd #815 Winthrop MA 02152

$625,000

Beds: 2

Baths: 2

Sq Ft: 1,203

Days on Market: 28

Updated 2 Minutes Ago

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Photo of 1 Seal Harbor Road #116 Winthrop MA 02152

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1 Seal Harbor Road #116 Winthrop MA 02152

$619,900

Beds: 2

Baths: 2

Sq Ft: 1,241

Days on Market: 17

Updated 2 Minutes Ago

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Photo of 142 Pleasant Street #12 Winthrop MA 02152

Open: Sunday 12:30 pm - 1:30 pm

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142 Pleasant Street #12 Winthrop MA 02152

$600,000

Beds: 2

Baths: 1.5

Sq Ft: 1,141

Days on Market: 68

Open: 7/12/26 12:30 PM - 1:30 PM

Updated 2 Minutes Ago

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Photo of 140 Shirley Street #220 Winthrop MA 02152

Open: Saturday 12 pm - 1:30 pm

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140 Shirley Street #220 Winthrop MA 02152

$589,900

Beds: 2

Baths: 1

Sq Ft: 782

Days on Market: 14

Open: 7/11/26 12 PM - 1:30 PM, 7/12/26 12 PM - 1:30 PM

Updated 2 Minutes Ago

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Photo of 1 Seal Harbor Rd #413 Winthrop MA 02152

Open: Saturday 10:30 am - 12 pm

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1 Seal Harbor Rd #413 Winthrop MA 02152

$578,000

-$1,000

Beds: 2

Baths: 2

Sq Ft: 1,205

Days on Market: 30

Open: 7/11/26 10:30 AM - 12 PM

Updated 2 Minutes Ago

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Photo of 16 Billows St #2 Winthrop MA 02152

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16 Billows St #2 Winthrop MA 02152

$565,000

Beds: 2

Baths: 1

Sq Ft: 928

Days on Market: 50

Updated 2 Minutes Ago

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Photo of 35 Somerset Ave. #3 Winthrop MA 02152

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35 Somerset Ave. #3 Winthrop MA 02152

$549,900

Beds: 2

Baths: 2

Sq Ft: 969

Days on Market: 80

Updated 2 Minutes Ago

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Photo of 10 Somerset #203 Winthrop MA 02152

Open: Saturday 10 am - 12 pm

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10 Somerset #203 Winthrop MA 02152

$549,000

Beds: 2

Baths: 1

Sq Ft: 869

Days on Market: 15

Open: 7/11/26 10 AM - 12 PM

Updated 2 Minutes Ago

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Photo of 52 Trident Ave #52 Winthrop MA 02152

Open: Saturday 11 am - 12 pm

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52 Trident Ave #52 Winthrop MA 02152

$499,000

-$11,000

Beds: 2

Baths: 1

Sq Ft: 1,006

Days on Market: 37

Open: 7/11/26 11 AM - 12 PM

Updated 2 Minutes Ago

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Photo of 34 Underhill St #4 Winthrop MA 02152

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34 Underhill St #4 Winthrop MA 02152

$495,000

Beds: 2

Baths: 2

Sq Ft: 903

Days on Market: 36

Updated 2 Minutes Ago

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Photo of 43 Sagamore Ave #1A Winthrop MA 02152

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43 Sagamore Ave #1A Winthrop MA 02152

$485,000

$20,000

Beds: 2

Baths: 1

Sq Ft: 913

Days on Market: 63

Updated 2 Minutes Ago

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Photo of 53 Trident Ave #301 Winthrop MA 02152

Open: Sunday 11 am - 12 pm

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53 Trident Ave #301 Winthrop MA 02152

$400,000

Beds: 2

Baths: 1

Sq Ft: 677

Days on Market: 29

Open: 7/12/26 11 AM - 12 PM

Updated 2 Minutes Ago

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Photo of 53 Trident #303 Winthrop MA 02152

Price Reduced

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53 Trident #303 Winthrop MA 02152

$399,900

-$100

Beds: 2

Baths: 1

Sq Ft: 664

Days on Market: 44

Updated 2 Minutes Ago

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Photo of 800 Governors Dr #6 Winthrop MA 02152

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800 Governors Dr #6 Winthrop MA 02152

$340,000

Beds: 2

Baths: 1

Sq Ft: 772

Days on Market: 44

Updated 2 Minutes Ago

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Photo of 173-175 Shirley St #2 Winthrop MA 02152

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173-175 Shirley St #2 Winthrop MA 02152

$300,000

Beds: 2

Baths: 1

Sq Ft: 698

Days on Market: 65

Updated 2 Minutes Ago

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Photo of 35 Perkins St #1 Winthrop MA 02152

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35 Perkins St #1 Winthrop MA 02152

$3,000 / mo

Beds: 2

Baths: 2

Sq Ft: 1,050

Days on Market: 36

Updated 2 Minutes Ago

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Photo of 800 Governors Dr #7 Winthrop MA 02152

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800 Governors Dr #7 Winthrop MA 02152

$2,800 / mo

Beds: 2

Baths: 1

Sq Ft: 909

Days on Market: 261

Updated 2 Minutes Ago

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Photo of 400 Governors Drive #5 Winthrop MA 02152

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400 Governors Drive #5 Winthrop MA 02152

$2,700 / mo

Beds: 2

Baths: 1

Sq Ft: 772

Days on Market: 40

Updated 2 Minutes Ago

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Photo of 235 Washington Ave #3 Winthrop MA 02152

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235 Washington Ave #3 Winthrop MA 02152

$2,650 / mo

Beds: 2

Baths: 1

Sq Ft: 900

Days on Market: 15

Updated 2 Minutes Ago

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Photo of 400 Governors Drive #39 Winthrop MA 02152

New Listing

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400 Governors Drive #39 Winthrop MA 02152

$2,600 / mo

Beds: 2

Baths: 1

Sq Ft: 800

Days on Market: 3

Updated 2 Minutes Ago

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