5-9 Family at 566 Shirley St, Winthrop MA 02152, Winthrop
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20 photos

$2,250,000

566 Shirley St, Winthrop MA 02152
Winthrop, MA 02152
Listed by Stephen Girolamo
Bedrooms
16
Bathrooms
6
Living area
5,553 sqft
Year built
1900

About this home

566 Shirley St contains six (6) units, consisting of two (2), 2-Bedroom/1-Bathroom units and four (4), 3-Bedroom/1-Bathroom units with 5,553 square feet of living area in 7,968 square feet of total gross area on a 0.09-acre corner parcel. The Property is across the street from the Crystal Cove Marina and is 1,000 feet from Winthrop Beach and the shores of the Atlantic Ocean. The Property has been well maintained and features all new common area lighting and carpeting, the foundation (interior and exterior) has been repointed. The Property has new blown-in insulation, and the rear deck system has been updated with refinished decks and new railings. The Property also has a new 11-camera security system and credit card operated washers and dryers. Two of the units have been fully renovated and two units have renovated bathrooms. The Property is separately metered for a mix of gas & electric powered heat & hot water, as well as electrictity. The Landlord provides town water & sewer.

Property details

MLS #
73554183
Property type
5-9 Family
Subdivision
N/A
Status
Active
Days on market
77
On market date
July 23, 2026
Stories
5
Total bathrooms
6
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.09 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 (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Arthur T. Cummings Elementary School
0.91 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
0.86 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
0.83 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).

85
Highly walkable
out of 100
EPA National Walkability Index
18.2 / 20 -- Most walkable
Google Places amenity density
75 / 100
Restaurants & cafes20
Grocery stores1
Parks15
Schools7
Transit stops20
Pharmacies0

Market position

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

On the market 77 days -- 2 fewer days than Winthrop's current average of 79 days.
For reference, the median list price across 229 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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Est. monthly payment
$13,700/mo
$450,000 down
$1,800,000 loan
Principal & interest$11,675
Property tax (est.)$1,875
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated July 27, 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.