About this home
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.
Listing last checked: Listing updated:
Listed by Beth Sager Group · Keller Williams Realty Boston Northwest · MLS #73515601
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Details at a glance
Interior4 property facts
- Rooms
- 10
- Heating
- Natural Gas
- Cooling
- Window Unit(s)
- Basement
- Yes · Unfinished
Building5 property facts
- Style
- 2 Family - 2 Units Up/Down
- Year built
- 1880
- Garage
- 1
- Parking
- 9
- Foundation
- Stone
Land & utilities5 property facts
- Lot size
- 0.12 acres
- Water
- Public
- Sewer
- Public Sewer
- Pool
- Not reported
- Zoning
- RG
Financial2 property facts
- Annual taxes
- $11,374
- Assessment year
- 2025
Location
Estimated monthly cost
Explore costs at the $1,110,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$6,561 / monthAdjust
- Principal & interest
- $5,613
- Property tax
- $948
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $11,374. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.
Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.
The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.
Price and status timeline
- New
$2,700 · Jun 11, 2026
- Lsd
$2,600 · Sold $2,600 · Jul 10, 2025
- Lsd
$2,600 · Sold $2,600 · Oct 31, 2024
- Lsd
$3,200 · Sold $3,200 · Oct 31, 2024
- Sld
$1,049,000 · Sold $1,071,000 · Oct 16, 2024
More property insights
Automated value estimate $1,197,796
Estimated range $1,106,831–$1,288,762.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisPhoto-based condition insights
Overall presentation: above average
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About 63-65 Harvard Street
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