Condo/Villa 2 Bedroom for Sale in Winthrop MA

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: 138

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: 47

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: 301

Updated 8 Minutes Ago

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Photo of 51 Harbor View Ave #3 Winthrop MA 02152

Price Reduced

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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: 40

Updated 8 Minutes Ago

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Photo of 51 Harbor View Ave #2 Winthrop MA 02152

Under Contract

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51 Harbor View Ave #2 Winthrop MA 02152

$659,000

-$16,000

Beds: 2

Baths: 1

Sq Ft: 1,220

Days on Market: 40

Updated 8 Minutes Ago

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Photo of 142 Pleasant #5 Winthrop MA 02152

Under Contract

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142 Pleasant #5 Winthrop MA 02152

$649,900

Beds: 2

Baths: 2.5

Sq Ft: 1,404

Days on Market: 251

Updated 8 Minutes Ago

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Photo of 3 Seal Harbor #344 Winthrop MA 02152

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3 Seal Harbor #344 Winthrop MA 02152

$649,000

Beds: 2

Baths: 2

Sq Ft: 1,302

Days on Market: 39

Updated 8 Minutes Ago

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Photo of 51 Harbor View Ave #1 Winthrop MA 02152

Price Reduced

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51 Harbor View Ave #1 Winthrop MA 02152

$639,000

-$11,000

Beds: 2

Baths: 1

Sq Ft: 1,213

Days on Market: 39

Updated 8 Minutes Ago

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Photo of 10 Somerset #201 Winthrop MA 02152

Under Contract

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10 Somerset #201 Winthrop MA 02152

$629,000

Beds: 2

Baths: 2

Sq Ft: 1,036

Days on Market: 126

Updated 8 Minutes Ago

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Photo of 140 Shirley Street #201 Winthrop MA 02152

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140 Shirley Street #201 Winthrop MA 02152

$624,900

Beds: 2

Baths: 1

Sq Ft: 874

Days on Market: 47

Updated 8 Minutes Ago

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Photo of 10 Somerset #206 Winthrop MA 02152

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10 Somerset #206 Winthrop MA 02152

$594,900

Beds: 2

Baths: 2

Sq Ft: 985

Days on Market: 271

Updated 8 Minutes Ago

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Photo of 10 Somerset #207 Winthrop MA 02152

Open: Tuesday 4:30 pm - 6:30 pm

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10 Somerset #207 Winthrop MA 02152

$569,000

Beds: 2

Baths: 1

Sq Ft: 898

Days on Market: 47

Open: 4/7/26 4:30 PM - 6:30 PM

Updated 8 Minutes Ago

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Photo of 130 Shirley Street #202 Winthrop MA 02152

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130 Shirley Street #202 Winthrop MA 02152

$549,900

Beds: 2

Baths: 1

Sq Ft: 782

Days on Market: 32

Updated 8 Minutes Ago

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Photo of 43 Sagamore Ave #1 Winthrop MA 02152

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43 Sagamore Ave #1 Winthrop MA 02152

$529,000

Beds: 2

Baths: 1

Sq Ft: 769

Days on Market: 25

Updated 8 Minutes Ago

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Photo of 26 Forrest #1 Winthrop MA 02152

Open: Friday 5 pm - 6:30 pm

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26 Forrest #1 Winthrop MA 02152

$515,000

Beds: 2

Baths: 1

Sq Ft: 1,325

Days on Market: 19

Open: 4/10/26 5 PM - 6:30 PM, 4/11/26 11 AM - 1 PM, 4/12/26 10 AM - 12 PM

Updated 8 Minutes Ago

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Photo of 35 Somerset Ave. #6 Winthrop MA 02152

Under Contract

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35 Somerset Ave. #6 Winthrop MA 02152

$499,900

Beds: 2

Baths: 2

Sq Ft: 800

Days on Market: 198

Updated 8 Minutes Ago

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Photo of 247 Washington #9 Winthrop MA 02152

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247 Washington #9 Winthrop MA 02152

$499,000

Beds: 2

Baths: 2

Sq Ft: 1,116

Days on Market: 18

Updated 8 Minutes Ago

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Photo of 49 Sagamore Ave #3A Winthrop MA 02152

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49 Sagamore Ave #3A Winthrop MA 02152

$459,900

Beds: 2

Baths: 1

Sq Ft: 1,079

Days on Market: 14

Updated 8 Minutes Ago

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Photo of 53 Trident Ave #204 Winthrop MA 02152

Under Contract

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53 Trident Ave #204 Winthrop MA 02152

$400,000

Beds: 2

Baths: 1

Sq Ft: 662

Days on Market: 61

Updated 8 Minutes Ago

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Photo of 800 Governors Dr #17 Winthrop MA 02152

Under Contract

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800 Governors Dr #17 Winthrop MA 02152

$375,000

Beds: 2

Baths: 1

Sq Ft: 811

Days on Market: 14

Updated 8 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: 220

Updated 8 Minutes Ago

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Photo of 36 Trident #B Winthrop MA 02152

Under Contract

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36 Trident #B Winthrop MA 02152

$3,000 / mo

Beds: 2

Baths: 1

Sq Ft: 1,100

Days on Market: 48

Updated 8 Minutes Ago

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Photo of 235 Washington Ave #2 Winthrop MA 02152

New Listing

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235 Washington Ave #2 Winthrop MA 02152

$2,975 / mo

Beds: 2

Baths: 1

Sq Ft: 900

Days on Market: 4

Updated 8 Minutes Ago

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Photo of 38 Trident Avenue #1 Winthrop MA 02152

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38 Trident Avenue #1 Winthrop MA 02152

$2,900 / mo

Beds: 2

Baths: 1

Sq Ft: 1,160

Days on Market: 171

Updated 8 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: 166

Updated 8 Minutes Ago

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