Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$949,000 Just Listed

  • For Sale
  • Active
  • Multi-Family
  • 2 Units
  • 7 Total Beds
  • 0.21 Acres
  • Updated 9 hours ago

Next open house:

Open House: 11:00 AM - 12:30 PM

Saturday 9/12 11:00 AM - 12:30 PM

190 Pleasant St,Winthrop, MA 02152

190 Pleasant StWinthropMA02152

Get directions

View more dates

Join us at 190 Pleasant St on:

  • Open House: 11:00 AM - 12:30 PM

    Sunday 9/13 11:00 AM - 12:30 PM

    190 Pleasant St,Winthrop, MA 02152
    190 Pleasant StWinthropMA02152
See This Home
Save This Home
See This Home
Save 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!

Full Property Details for 190 Pleasant St

General

  • Price: $949,000
  • Taxes: $10,175 (2026)
  • Status: Active
  • Type: Multi-Family
  • MLS ID: 73573129
  • Updated: 9/9/2026
  • Added to Site: 1 day(s) ago

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 2
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 7

Parking

  • Parking Features: Paved Drive, Off Street

Location

  • County: Suffolk

Structural Information

  • Basement: Yes
  • Stories/Levels: 3
  • Square Feet: 4,251
  • Year Built: 1890

Lot Features

  • Lot Size (Acres): 0.21

Financial Considerations

  • Tax Amount: $10,175
  • Tax Year: 2026

Disclosures and Reports

  • Disclosures/Rstr.: UNIT 2 WILL BE DELIVERED VACANT
  • Property ID: M:0029 B:0123 L:0000, 1421836

Listed by REMAX Andrew Realty Services, Michael MacDonald and Guy Contaldi

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agents

— 190 Pleasant St —

  • Michael MacDonald

    REMAX Andrew Realty Services

  • Guy Contaldi

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 190 Pleasant St

School District:Winthrop School District
NameGradesDistance
Arthur T. Cummings Elementary School
40 Hermon Street, Winthrop, MA 02152
3-50.3 mi
William P. Gorman/Fort Banks Elementary School
101 Kennedy Drive, Winthrop, MA 02152
PK-20.9 mi
Winthrop Middle School, Winthrop, MA
60 Payson Street, Winthrop, MA 02152
6-80.7 mi
Winthrop Sr High School
400 Main Street, Winthrop, MA 02152
9-120.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 190 Pleasant St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/08/2026
Listed
$949,000
46.22%
MLS
8/23/2022
Sold
$649,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 190 Pleasant St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$9,008
16%
$872,900
17%
2024
$7,752
-12%
$744,000
-9%
2023
$8,760
2%
$818,700
12%
2022
$8,611
2%
$732,200
10%
2021
$8,423
3%
$664,300
2%
2020
$8,195
2%
$649,400
6%
2019
$8,073
2%
$612,500
10%
2018
$7,887
9%
$557,000
11%
2017
$7,245
6%
$502,800
13%
2016
$6,827
13%
$444,200
5%
2015
$6,051
6%
$422,000
15%
2014
$5,726
—
$367,500
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 190 Pleasant St

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by REMAX Andrew Realty Services, Michael MacDonald and Guy Contaldi

Similar Properties near 190 Pleasant St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

126 Leyden St, Boston, MA 02128 - Photo 1
$895,000

126 Leyden St  Boston, MA 02128

  • Multi-Family
  • Active
  • Updated 4 days ago
  • 3
    Units
  • 6
    Total Beds
  • 0.05
    Acres
49 George Ave, Revere, MA 02151 - Photo 1 Just Listed
$930,000

49 George Ave  Revere, MA 02151

  • Multi-Family
  • Active
  • Updated 1 day ago
  • 2
    Units
  • 6
    Total Beds
  • 0.08
    Acres
88 Trenton St, Boston, MA 02128 - Photo 1
$899,000

88 Trenton St  Boston, MA 02128

  • Multi-Family
  • Active
  • Updated 2 days ago
  • 2
    Units
  • 8
    Total Beds
  • 0.06
    Acres
74 Trenton St, Boston, MA 02128 - Photo 1
$988,000

74 Trenton St  Boston, MA 02128

  • Multi-Family
  • Active
  • Updated 5 days ago
  • 3
    Units
  • 7
    Total Beds
  • 0.04
    Acres
Listed by Lu Ouyang (617) 763-0708

Just Listed near 190 Pleasant St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

22 Lancaster Ave, Revere, MA 02151 - Photo 1 Just Listed
$709,900
Open House

22 Lancaster Ave  Revere, MA 02151

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,326
    Sq. Ft.
Listed by Nick Silvestri (617) 646-9481
17 Mill St, Revere, MA 02151 - Photo 1 Just Listed
$849,000

17 Mill St  Revere, MA 02151

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,032
    Sq. Ft.
Listed by Lisa Licata-Schepici (781) 244-5566
175 Rumney Rd, Revere, MA 02151 - Photo 1 Just Listed
$899,000

175 Rumney Rd  Revere, MA 02151

  • Single Family
  • Active
  • Updated 9 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,327
    Sq. Ft.
Listed by Lisa Licata-Schepici (781) 244-5566
59 Larkin St, Revere, MA 02151 - Photo 1 Just Listed
$999,999
Open House

59 Larkin St  #2  Revere, MA 02151

  • Townhouse
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,904
    Sq. Ft.

Price Reduced near 190 Pleasant St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

43 Dashwood St, Revere, MA 02151 - Photo 1 Price Reduced
-$35,000 (-5.11%)
$650,000
Open House

43 Dashwood St  Revere, MA 02151

  • Multi-Family
  • Active
  • Updated 1 hour ago
  • 2
    Units
  • 4
    Total Beds
  • 0.04
    Acres
28 S, Revere, MA 02151 - Photo 1 Price Reduced
-$80,000 (-11.78%)
$599,000
Open House

28 S  Revere, MA 02151

  • Single Family
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,557
    Sq. Ft.
176 Reservoir Ave, Revere, MA 02151 - Photo 1 Price Reduced
-$21,000 (-2.92%)
$699,000
Open House

176 Reservoir Ave  Revere, MA 02151

  • Single Family
  • Active
  • Updated 9 hours ago
  • 3
    Beds
  • 1
    Total Bath
  • 2,203
    Sq. Ft.
172 Harris St, Revere, MA 02151 - Photo 1 Price Reduced
-$20,000 (-2.5%)
$779,900
Open House

172 Harris St  Revere, MA 02151

  • Single Family
  • Active
  • Updated 9 hours ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,944
    Sq. Ft.

Recent Sales near 190 Pleasant St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

44 Cottage Park Rd, Winthrop, MA 02152 - Photo 1 Sold
$900,000

44 Cottage Park Rd  Winthrop, MA 02152

  • Multi-Family
  • Closed
  • 2
    Units
  • 6
    Total Beds
  • 0.09
    Acres
57 Loring Rd, Winthrop, MA 02152 - Photo 1 Sold
$960,000

57 Loring Rd  Winthrop, MA 02152

  • Single Family
  • Closed
  • Updated 7 days ago
  • 5
    Beds
  • 2
    Total Baths
  • 2,123
    Sq. Ft.
308 Bowdoin, Winthrop, MA 02152 - Photo 1 Sold
$999,900

308 Bowdoin  Winthrop, MA 02152

  • Multi-Family
  • Closed
  • 2
    Units
  • 7
    Total Beds
  • 0.15
    Acres
18-20 Fairview Steet, Winthrop, MA 02151 - Photo 1 Sold
$855,000

18-20 Fairview Steet  Winthrop, MA 02151

  • Multi-Family
  • Closed
  • 3
    Units
  • 5
    Total Beds
  • 0.24
    Acres
Listed by Laura "B" Team

190 Pleasant St, Winthrop, MA 02152 (MLS# 73573129) is a Multi-Family property with 2 units containing 7 bedrooms, 2 full bathrooms and 2 partial bathrooms. 190 Pleasant St is currently listed for $949,000 and was received on September 08, 2026. Want to learn more about 190 Pleasant St? Do you have questions about finding other Multi-Family real estate for sale in Winthrop? You can browse all Winthrop real estate or contact a Coldwell Banker agent to request more information.

Tour this property