Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 2 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 3 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 4 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 5 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 6 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 7 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 8 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 9 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 10 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 11 of 12
Multi Family at 104-106 Shirley St, Winthrop MA 02152, Winthrop, photo 12 of 12
12 photos

$749,974

104-106 Shirley St, Winthrop MA 02152
Winthrop, MA 02152
Listed by Mission Impossible Team
Bedrooms
5
Bathrooms
2
Living area
2,520 sqft
Year built
1910

About this home

Attention investors, builders, and contractors! A truly rare opportunity awaits at 104-106 Shirley Street, Winthrop. Situated on an impressive double lot spanning over 10,000 square feet, this property offers incredible upside and potential. The existing home features some fire damage, allowing buyers the flexibility to perform selective renovations, execute a partial demo, or complete a full renovation to suit their vision. Double lots of this footprint are nearly impossible to find in Winthrop, making it an ideal project for tradespeople, savvy investors and whoever looking to add substantial value. Located just minutes from beaches, shops, dining, transit, and a short commute into Boston and Logan Airport, the site and scale are exceptional. Property is being sold strictly in AS-IS, WHERE-IS condition with all faults. Seller or broker make no representations or warranties, express or implied. Buyer to perform all due diligence regarding condition, zoning, permits to able to build , and scope of work

Property details

MLS
MLS Property Information Network
MLS #
73592145
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
1
On market date
October 17, 2026
Stories
2
Total bathrooms
2
Garage spaces
2
Parking spaces
6
Lot size
0.24 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
William P. Gorman/Fort Banks Elementary
0.33 mi away · Grades -1-2
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
481
Student:teacher ratio
12.7:1
District
Winthrop
Middle
Winthrop Middle School
0.21 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
0.22 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). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

81
Highly walkable
out of 100
EPA National Walkability Index
16.2 / 20 -- Most walkable
Google Places amenity density
80 / 100
Restaurants & cafes20
Grocery stores1
Parks20
Schools11
Transit stops20
Pharmacies1

Market position

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

On the market 1 days -- 84 fewer days than Winthrop's current average of 85 days.
For reference, the median list price across 236 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.

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Adjust tax / insurance estimates
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Est. monthly payment
$4,666/mo
$149,995 down
$599,979 loan
Principal & interest$3,891
Property tax (est.)$625
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 1 days ago.

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.