5+ Family - 5+ Units Side by Side at 1001 Shirley St, Winthrop MA 02152, Winthrop
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34 photos

$4,724,900

1001 Shirley St, Winthrop MA 02152
Winthrop, MA 02152
Listed by The Legacy Group
Bedrooms
10
Bathrooms
12.5
Living area
9,156 sqft
Year built
1955

About this home

Rooted in history & reimagined with intention, The Pearl is a one-of-a-kind five-unit multifamily property by the coast in Winthrop. Formerly a church, the building has been thoughtfully transformed into five distinct loft-style residences, each with its own layout, character & design identity. Original architectural details including exposed beams, hardwood floors, oversized windows & dramatic ceiling heights are balanced with modern finishes throughout. Each residence features Bosch appliances, electric fireplaces, in-unit laundry, radiant heated primary baths, walk-in closets, hidden powder rooms, concealed storage, private outdoor space with automated retractable awnings, additional storage & two off-street parking spaces. Located near Winthrop’s beaches, harbor walks, cafés, restaurants & commuter access into Boston, The Pearl offers a special opportunity to own a boutique coastal multifamily with historic character, strong design & flexible long-term potential.

Highlights

Fireplace

Property details

MLS #
73531014
Property type
5+ Family - 5+ Units Side by Side
Subdivision
N/A
Status
Active
Days on market
126
On market date
June 4, 2026
Stories
10
Total bathrooms
12.5
Garage spaces
N/A
Parking spaces
10
Lot size
0.35 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
1.4 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
1.49 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
1.47 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).

59
Somewhat walkable
out of 100
EPA National Walkability Index
13.7 / 20 -- Above average walkable
Google Places amenity density
45 / 100
Restaurants & cafes8
Grocery stores0
Parks12
Schools0
Transit stops20
Pharmacies0

Market position

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

On the market 126 days -- 47 more 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
$28,604/mo
$944,980 down
$3,779,920 loan
Principal & interest$24,516
Property tax (est.)$3,937
Home insurance (est.)$150

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Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated June 9, 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.