Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 2 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 3 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 4 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 5 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 6 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 7 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 8 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 9 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 10 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 11 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 12 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 13 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 14 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 15 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 16 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 17 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 18 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 19 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 20 of 21
Multi Family at 190 Pleasant St, Winthrop MA 02152, Winthrop, photo 21 of 21
21 photos

$949,000

190 Pleasant St, Winthrop MA 02152
Winthrop, MA 02152
Listed by Michael MacDonald
Bedrooms
7
Bathrooms
3
Living area
4,251 sqft
Year built
1890

About this home

Welcome to 190 Pleasant Street, a spacious two-family home offering approximately 4,251 square feet of living space across three levels. Featuring 13 total rooms,seven bedrooms, two full bathrooms and two half bathrooms, this property presents an excellent opportunity for an owner-occupant, investor or multigenerational household. Each unit offers generous living space, while the home’s flexible layout provides plenty of potential to customize and add value. Conveniently located near Winthrop’s beaches, local shops, restaurants, public transportation and Boston. Bring your vision and discover everything this well-located two-family property has to offer!

Property details

MLS #
73573129
Property type
Multi Family
Subdivision
N/A
Status
Active
Days on market
30
On market date
September 8, 2026
Stories
3
Total bathrooms
3
Garage spaces
N/A
Parking spaces
8
Lot size
0.21 acres
Loading map…

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
0.34 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
0.68 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). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

69
Walkable
out of 100
EPA National Walkability Index
12.3 / 20 -- Above average walkable
Google Places amenity density
80 / 100
Restaurants & cafes20
Grocery stores1
Parks20
Schools10
Transit stops20
Pharmacies1

Market position

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

On the market 30 days -- 49 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.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$5,865/mo
$189,800 down
$759,200 loan
Principal & interest$4,924
Property tax (est.)$791
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 26 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.