Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside.
| Units | 2 |
| Living area | 2,186 sqft |
| Lot size | 5,118 sqft |
| Year built | 1880 |
| Price / sqft | $526 |
| County | Middlesex |
| MLS # | 73515601 |
| Days on market | 4 days |
| Listed on | May 9, 2026 |
| Annual property tax | $11,374 |
| Tax year | 2025 |
| Assessed value | $1,025,600 |
| Zoning | RG |
| Gross income (actual) | $72,000/yr |
| Net operating income (actual) | $72,000/yr |
| Total actual rent | $6,000/mo |
| Stories | 3 |
| Total rooms | 10 |
| Lot size | 0.12 acres |
| Garage spaces | 1 |
| Parking spaces | 9 |
| Parking | Paved Drive |
| Basement | Unfinished |
| Foundation | Stone |
| Heating | Natural Gas |
| Cooling | Window Unit(s) |
| Sewer | Public Sewer |
| Water | Public |
Listing courtesy of Keller Williams Realty Boston Northwest — Beth Sager Group. Listing data © MLS PIN.
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It is a 2-unit multi-family property with 2,186 sqft of living area, built in 1880.
63-65 Harvard Street, Winchester MA 01890 has been listed for 4 days (since May 9, 2026).
Annual property taxes are $11,374 (2025), on an assessed value of $1,025,600.
At $1,150,000 for 2,186 sqft, that's about $526 per square foot.
1 garage space and 9 total parking spaces (paved drive).
63-65 Harvard Street, Winchester MA 01890 is in Winchester, Middlesex County, MA 01890.