
63-65 Harvard Street Winchester — Photo 1 of 33
Recent Drop: $40,000
$1,110,000
Winchester, MA 01890
Beds
5
Baths
3
SqFt
2,186
Style
2 Family - 2 Units Up/Down
Built
1880
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.
* Analysis is based on 24 actively listed and recently sold comparable properties strictly within Winchester, MA.
Was $1,150,000
Aug 10, 2026
MLS® 73515601
Jun 11, 2026
MLS® 73534454
May 9, 2026
MLS® 73515601
Jul 25, 2025
MLS® 73402642
Jul 10, 2025
MLS® 73402642
Jan 19, 2025
MLS® 73308335
Dec 15, 2024
MLS® 73308333
Dec 5, 2024
MLS® 73302727
Oct 31, 2024
MLS® 73308335
Oct 31, 2024
MLS® 73308333
Oct 16, 2024
MLS® 73302727
23,406
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$230K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
18.3%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
2,667 housing units permitted in the last 12 months (-2% vs the prior 12 months) — 1,709 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Listing Agent: Beth Sager Group
Listing Office: Keller Williams Realty Boston Northwest
MLS® Number: 73515601
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