Upcoming open house
Sat, Oct 17 · 11:00 AM–12:30 PM
Arrive prepared. Get the October 2026 Winthrop Bean Group Buyer’s Guide before you tour.
About this home
PRICE IMPROVEMENT! 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!
Listing last checked: Listing updated:
Listed by Michael Macdonald · REMAX Andrew Realty Services · MLS #73573129
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Details at a glance
Interior3 property facts
- Rooms
- 13
- Flooring
- Tile, Carpet, Laminate, Hardwood
- Basement
- Yes · Full
Building5 property facts
- Style
- Multi Family
- Year built
- 1890
- Parking
- 8
- Foundation
- Concrete Perimeter
- Roof
- Shingle
Land & utilities5 property facts
- Lot size
- 0.21 acres
- Water
- Public
- Sewer
- Public Sewer
- Pool
- Not reported
- Zoning
- R3
Financial2 property facts
- Annual taxes
- $10,175
- Assessment year
- 2026
Location
Estimated monthly cost
Explore costs at the $899,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$5,394 / monthAdjust
- Principal & interest
- $4,546
- Property tax
- $848
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $10,175. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
More property insights
Automated value estimate $991,618
Estimated range $948,358–$1,034,879.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisPhoto-based condition insights
Overall presentation: average
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About 190 Pleasant St
Can I request a private showing?
Request a tour of 190 Pleasant St and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
Availability varies by property and source. Request the documents you need and we will help obtain what is available.