50 Main St, Winthrop, MA, 02152
About This Home
Excellent opportunity to own a well-maintained 2-family property in the highly desirable seaside community of Winthrop! Perfect for investors, owner-occupants or multi-generational living, this spacious property offers two large units featuring 3 bedrooms,1 full bathroom, hardwood floors, generous living areas and a bonus office room! Separate utilities and washer/dryer hookups add convenience and value for both owners and tenants. The property also offers plenty off-street parking, a paved driveway, and a private outdoor area. Conveniently located near restaurants, shopping, public transportation, beaches, Logan Airport, and major highways, making commuting into Boston quick and easy. Strong rental demand in the area creates excellent income potential and long-term upside. Whether you are looking to expand your investment portfolio, generate steady rental income or occupy one unit while collecting rent from the other, this property checks all the boxes!
Getting Around
Somewhat Walkable
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1850
Materials
- Foundation: Block,Stone
- Roof: Shingle
- Construction materials: Frame
Type & Style
- Home type: MultiFamily
- Property subType: Multi Family
Interior
Appliances
- Appliances included: Range,Refrigerator,Range Hood,Dishwasher
- Laundry features: Gas Dryer Hookup,Washer Hookup
Basement
- Has basement: Yes
- Basement: Unfinished
Bedrooms & Bathrooms
- Bedrooms: 6
- Bathrooms: 2
- Full bathrooms: 2
Features
- Ceiling Fan(s),Walk-In Closet(s),Bathroom With Tub,Bathroom with Shower Stall,Living Room,Kitchen,Mudroom
- Flooring: Tile,Vinyl,Laminate,Hardwood
- Finished area above ground: 2,560
Heating
- Heating features: Hot Water,Natural Gas,Baseboard,Electric
Interior Area
- Total structure area: 2,560
- Total interior livable area: 2,560 sqft
Property
Details
- Parcel number: M:0053 B:0009 L:0000,1423661
- Zoning: R
Features
- Patio & porch: Deck - Wood
- Exterior features: Rain Gutters
- Fencing: Fenced
- Waterfront features: Ocean,0 to 1/10 Mile To Beach,Beach Ownership(Public)
Lot
- Lot size: 5,671 sqft
Parking
- Total spaces: 8
- Parking features: Paved Drive,Off Street,Driveway,Paved
- Has uncovered spaces: Yes
- Uncovered spaces: 8
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Coastal Flooding
- Heat Wave
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters Across Massachusetts Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $4,045 | $48,540 |
| Home Insurance * | $326 | $3,912 |
| Property Taxes | $683 | $8,196 |
| Electricity | $504 | $6,057 |
| Total | $5,558 | $66,696 |
Income You'd Need if You Spent...
Massachusetts FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-06-03 | Price change | $799,986 |
| 2026-05-26 | Listed for sale | $829,986 |
| 2022-06-08 | Listing removed | $750,000 |
| 2022-03-23 | Listed for sale | $750,000 |
| 1997-06-25 | Sold | $75,200 |
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