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$1,600,000

516 Pleasant St, Winthrop MA 02152
Winthrop, MA 02152
Listed by Amanda George
Bedrooms
5
Bathrooms
3
Living area
2,889 sqft
Year built
1900

About this home

Every evening, the harbor turns amber from the west, 516 Pleasant Street has a front-row seat. A one-of-a-kind home set along Winthrop's harbor front with direct water access, a concrete seawall, and a private boat launch, this residence offers a lifestyle that cannot be assembled from scratch in today's coastal market. The rights to rebuild a pier remain intact, a dormant asset in a harbor where private moorings are nearly impossible to find. The units span 2,889 square feet across three floors, and this home could easily be transformed into the single-family of your dreams. An in-ground pool, roof deck, sunroom with gas stove, and west-facing harbor views complete the picture. Many updates include replacement windows, mass-save insulation, professional landscaping and irrigation, mini-splits, replacement chimney liner, hunter-douglas shades, front porch replacement, and more. Close to logan sirport, Rt 1A, ferry service to Boston, parks, summer farmers market and more!

Highlights

WaterfrontViewFireplace

Property details

MLS #
73541145
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
N/A
On market date
N/A
Stories
3
Garage spaces
N/A
Lot size
0.2 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

Elementary
Arthur T. Cummings Elementary School
0.38 mi away · Grades 3-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
415
Student:teacher ratio
11.9:1
District
Winthrop
Middle
Winthrop Middle School
0.63 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
423
Student:teacher ratio
11.1:1
District
Winthrop
High
Winthrop High School
0.64 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
564
Student:teacher ratio
13.4:1
District
Winthrop

Mortgage calculator

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Est. monthly payment
$9,785/mo
$320,000 down
$1,280,000 loan
Principal & interest$8,302
Property tax (est.)$1,333
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 28, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.