Multi Family at 50 Main St, Winthrop
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$779,986

50 Main St
Winthrop, MA 02152
Listed by Matt Tasgin
Bedrooms
6
Bathrooms
2
Living area
2,560 sqft
Year built
1850

About this home

PRICE REDUCTION! Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience and value for both owners and tenants. The property also offers plenty off-street parking, a paved driveway, and a private outdoor area. Conveniently located near restaurants, shopping, public transportation, beaches, Logan Airport, and major highways, making commuting into Boston quick and easy. Strong rental demand in the area creates excellent income potential and long-term upside. Whether you are looking to expand your investment portfolio, generate steady rental income or occupy one unit while collecting rent from the other, this property checks all the boxes!

Property details

MLS
MLS Property Information Network
MLS #
73523937
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
161
On market date
May 26, 2026
Stories
2
Total bathrooms
2
Garage spaces
N/A
Parking spaces
8
Lot size
0.13 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Arthur T. Cummings Elementary School
0.5 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
0.64 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
0.66 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

Walkability

Blended score for Winthrop's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

86
Highly walkable
out of 100
EPA National Walkability Index
17.2 / 20 -- Most walkable

Market position

How this listing compares to current activity in Winthrop, from live MLS data.

On the market 161 days -- 70 more days than Winthrop's current average of 91 days.
For reference, the median list price across 257 active listings in Winthrop right now is $499,900.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

Adjust tax / insurance estimates
Est. monthly payment
$4,847/mo
$155,997 down
$623,989 loan
Principal & interest$4,047
Property tax (est.)$650
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network. Last updated September 12, 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.