217 Pleasant Street Winthrop — Photo 1 of 39
Recent Drop: $30,000
$949,900
217 Pleasant Street, Winthrop, MA 02152
Winthrop, MA 02152
Beds
6
Baths
2.5
SqFt
3,263
Style
Single Family
Built
1896
NEW PRICE and an exceptional value for this home. It’s an opportunity to make it your own and enjoy the quaint town of Winthrop by the sea. Spacious and beautifully updated, 6-bedroom, 2.5-bath home with the perfect blend of classic character & modern efficiency, all located in the wonderful seaside community of Winthrop by the Sea. Featuring gleaming hardwood floors throughout, newer windows 2 fireplaces giving warmth & charm to the living spaces. Extensive updates include all new mechanical systems including elec. wiring, FWA furnace, cent A/C, on-demand HW, mini-split heat pump/AC units, plumbing lighting, all providing peace of mind for years to come. Generous space, new paint & plaster finishes, & a beautifully finished basement for extra-living space, or entertainment. Kitchen has S.S. appliances and convenient 1st fl stacked washer & dryer. Outside large welcoming porch, groomed backyard, newer asphalt driveway, & an updated 2-car garage w/new overhead doors. Energy conscious buyers can assume the term note solar panels. OPEN HOUSE Saturday 10/3 1100-12:30
Key facts
It was listed on August 25, 2026. The price has come down from an original $998,900 to $949,900 across 2 changes, most recently on September 29, 2026. The annual property taxes are $9,003 (2026 tax year). It sits on a 0.14-acre (6,210 sq ft) lot.
Open Houses
Market Value Analysis
* Analysis is based on 22 actively listed and recently sold comparable properties strictly within Winthrop, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Tankless Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Washer • Dryer • Plumbed For Ice Maker
Neighborhood
Public Transportation • Park • Golf
Geography
Property History
$949,900
Was $979,900
Sep 29, 2026
MLS® 73567723
$979,900
Was $998,900
Sep 11, 2026
MLS® 73567723
$998,900
Aug 25, 2026
MLS® 73567723
$999,000
Aug 24, 2026
MLS® 73540636
$999,000
Jun 24, 2026
MLS® 73540636
Questions about this home
When was 217 Pleasant Street, Winthrop listed?
217 Pleasant Street, Winthrop was listed on August 25, 2026.
Has the price of 217 Pleasant Street, Winthrop changed?
The price has come down from an original $998,900 to $949,900 across 2 changes, most recently on September 29, 2026.
What are the property taxes for 217 Pleasant Street, Winthrop?
The annual property taxes for 217 Pleasant Street, Winthrop are $9,003 (2026 tax year).
How big is the lot at 217 Pleasant Street, Winthrop?
217 Pleasant Street, Winthrop sits on a 0.14-acre (6,210 sq ft) lot.
What is the status of 217 Pleasant Street, Winthrop?
217 Pleasant Street, Winthrop is actively listed for sale.
Population
18,759
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
Median Household Income
$116K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
Renter-Occupied Homes
43.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
New Construction Permits — Suffolk County
2,337 housing units permitted in the last 12 months (+13% vs the prior 12 months) — 2,062 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '26)
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,263 sq ft principal dwelling). Lot size: 6,210 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Listing Agent: Louis Bonavita
Listing Office: Benton Real Estate Company
MLS® Number: 73567723
