
217 Pleasant Street Winthrop — Photo 1 of 39
Recent Drop: $200,000
$999,000
Winthrop, MA 02152
Beds
6
Baths
2.5
SqFt
3,263
Style
Single Family
Built
1896
PRICE IMPROVEMENT, not another reduction, but an opportunity to make this your own. 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.
* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Winthrop, MA.
Gas Water Heater • Tankless Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Washer • Dryer • Plumbed For Ice Maker
Public Transportation • Park • Golf
Was $1,099,000
Jul 21, 2026
MLS® 73540636
Was $1,149,000
Jul 16, 2026
MLS® 73540636
Was $1,199,000
Jul 15, 2026
MLS® 73540636
Jun 24, 2026
MLS® 73540636
18,759
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$116K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
43.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
2,527 housing units permitted in the last 12 months (+37% vs the prior 12 months) — 2,269 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
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: 73540636
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