190 Pleasant St, Winthrop MA 02152
Winthrop, MA 02152
$949,000
Est. $5,847/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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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!
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Sep 8, 2026
$949,000
Original listing
Office: REMAX Andrew Realty Services
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 09/08/2026 | 🏠 Listed for Sale | $949,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $10,175 | $913,400 |
Financial Details
Annual Property Tax
$10,175
Tax Year 2026
Assessed Value
$913,400
Facts & Features
Home Facts
Type
Residential Income
Style
Multi Family
Year Built
1890
Living Area
4,251 sq ft
Lot Size
0.21 acres
Stories
3
Bedrooms
4
Full Baths
2
Half Baths
2
Total Rooms
13
Investment Metrics
Units
2
Unit 1 Rent
$3,000/mo · N
Unit 2 Rent
— · N
Total Monthly Rent
$3,000/mo
Gross Income
$36,000
Net Operating Income
$36,000
Cap Rate
3.79%
Interior
Heating
None
Cooling
None
Flooring
Tile, Carpet, Laminate, Hardwood
Appliances
None
Fireplace
None
Basement
Full
Laundry
None
Features
Living Room, Dining Room, Kitchen, Office/den, Family Room, Laundry Room
Exterior
Construction
Frame
Architecture
None
Roof
Shingle
Features
None
Pool
None
Spa
None
Fencing
None
Patio/Porch
None
Parking
Features
Paved Drive, Off Street
Total Spaces
8
Utilities
Electric
None
Water
Public
Sewer
Public Sewer
Gas
None
Other
None
Financial
Annual Tax
$10,175
Assessed Value
$913,400
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
MA Disclosures
Lead Paint
Unknown
Seller Disclosures
Unit 2 Will Be Delivered Vacant
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Suffolk
Property Overview
Property Type
Multi Family
Listing Type
For Sale
Year Built
1890
Bedrooms
4
Full Bathrooms
2
Half Bathrooms
2
Living Area
4,251 sq ft
Total Rooms
13
Stories
3
Levels
3
Floor Layout
Interactive room guide
Floor Layout
Finished Area
4,251 sq ft above grade
Display Options
Room Markers
OOffice (1)
KKitchen (1)
BRBedroom (5)
BABathroom (4)
DDining (1)
LLiving (2)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Tile, Carpet, Laminate, Hardwood
Appliances:
Interior Features:
Living Room, Dining Room, Kitchen, Office/Den, Family Room, Laundry Room
Windows:
Insulated Windows
Basement:
Full
Laundry:
Security:
Construction & Materials
Year Built:
1890
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Concrete Perimeter
Stories:
3
Heating, Cooling & Utilities
Heating:
Cooling:
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Patio & Porch:
Fencing:
Other Structures:
Lot Features:
Level
Road Surface:
Parking & Garage
Total Parking Spaces:
8
Parking Features:
Paved Drive, Off Street
Nearby Schools
School District
Winthrop School District local
C
School Safety
2024-25
0.3%
Low
0.3%
Suspensions
5.2% below state avg
Elementary Schools
2 schools
B-
Arthur T. Cummings Elementary School
0.3 mi
|
#447 of 825
|
Score: 46.2
Improved 107 spots from last year
-12 below state avg
466 students
Moderate
Rising School
Grades 03-05
William P. Gorman/Fort Banks Elementary School
1.0 mi
486 students
Moderate
Grades PK-02
Middle Schools
1 school
B+
Winthrop Middle School
0.7 mi
|
#118 of 352
|
Score: 47.7
Dropped 25 spots from last year
-10.5 below state avg
455 students
Moderate
Grades 06-08
High Schools
1 school
C+
Winthrop High School
0.7 mi
|
#238 of 346
|
Score: 48.4
Dropped 109 spots from last year
-9.8 below state avg
553 students
Moderate
18 sports
• 1,118 athletes
High Graduation Rate
College Ready Curriculum
Strong Athletics
Grades 09-12
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Monthly Payment Calculator
Monthly Payment
$0
Principal, interest, taxes & insurance
Loan Amount
$0
After down payment
Total Interest
$0
Over life of loan
Total Cost
$0
Including down payment
%
Down: $0
%
Monthly Payment Breakdown
Principal & Interest
$0
Property Tax
$848
Homeowners Insurance
$200
PMI (if <20% down)
$0
Loan Summary
Total of 360 payments
$0
Total principal paid
$0
Total interest paid
$0
Rate Impact
-0.5% Rate
$0/mo
Save $0/mo
Current Rate
$0/mo
+0.5% Rate
$0/mo
Cost $0/mo
Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.
Location
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Neighborhood
190 Pleasant St, Winthrop MA 02152
Winthrop, MA 02152
Listing Information
Listing Agent
Michael MacDonald
Listing Office
REMAX Andrew Realty Services
Office Phone
781-395-7676
Agent MLS ID
CN235860
Office MLS ID
AC2354
Listing Data Updated
Sep 8, 2026 12:34 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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