217 Pleasant Street Winthrop — Photo 1 of 39
Recent Drop: $19,000
$979,900
Investment Analysis — 217 Pleasant Street
Winthrop, MA 02152
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 6-bedroom in 02152 carries an estimated $3,470/mo in gross rent — about a 2.31% cap rate and $22,643/yr in estimated NOI at the $979,900 list price. Adjust every assumption in the calculator below.
Beds
6
Baths
2.5
SqFt
3,263
Style
Single Family
Built
1896
Stop by our OPEN HOUSE Sunday 9/13 1:00-2:30 for a viewing. A fantastic 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.
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Open Houses
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
$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
Listing Agent: Louis Bonavita
Listing Office: Benton Real Estate Company
MLS® Number: 73567723
