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.
This home has been viewed 11 times
Last Checked: May 14th, 2026 at 5:03am (Source: MLS PIN #73515601)
Gross Income: $72,000
Gross Expenses: $11,374
Net Income Calc: $60,626
Annual Expenses for 63-65 Harvard Street, Winchester MA 01890
Total Gross Expenses (Calculated)$11,374/year
APOD AvailableNo
Heating
Electricity
Water
Gas
Insurance
Sewer
Trash Removal
Repair & Maintenance
Management
Miscellaneous
Real Estate Tax11374
Annual Income & Unit Breakdown for 63-65 Harvard Street, Winchester MA 01890
Total Gross Income (Calculated)$72,000
Unit 1
Rental Income$0
LeaseY
Bedrooms2
Bathrooms1 Full
Floor1
Levels in Unit1
Rent Includes
Unit 2
Rental Income$0
LeaseY
Bedrooms3
Bathrooms2 Full
Floor2
Levels in Unit2
Rent Includes
General Information for 63-65 Harvard Street, Winchester MA 01890
Listing ID73515601
Property TypeMulti Family / 2 Family
Price1150000 ($526.08/SqFt)
Style2 Family - 2 Units Up/down
CityWinchester
CountyMiddlesex
Neighborhood(s)
Approximate Living Area Total2186
Approximate Lot Size (Acres)0.12
Total Parking10 (1 Garage)
Garage Parking1
Year Built1880
Year Built SourcePublic Records
Year Built DetailsApproximate
WaterPublic
SewerPublic Sewer
Electric
Hot Water
Roof Material
BasementFull
Construction Materials
Lot Features
Foundation Description
Accessible Features
Outdoor Space
ZoningRG
Water Views
Water Views Features
Waterfront0
Waterfront Features
Terms
Disclosures for 63-65 Harvard Street, Winchester MA 01890
Lead PaintNone
UFFI
Living Area Includes BasementNo
Living Area Disclosure
Building Area SourcePublic Records
ExclusionsFireplace Mantel In Living Room Is Excluded.
Financial Data Source
Total Gross Expenses By Broker
Total Gross Income By Broker
Total Net Income By Broker
Short Sale / Forclosure (Bank Owned)
Compensation Based On
Financial Information for 63-65 Harvard Street, Winchester MA 01890
Real Estate Taxes11374
Tax Year2025
Assessed Value$1,025,600
Financial Data Source
Total Gross Expenses By Broker
BostonRealEstate.com Gross Expenses
Total Gross Income By Broker
BostonRealEstate.com Gross Income
Total Net Income By Broker
BostonRealEstate.com Gross NOI
CAP Rate (based on Broker info)
Location Information for 63-65 Harvard Street, Winchester MA 01890
Neighborhood(s)
Area Amenities
Contact Information for 63-65 Harvard Street, Winchester MA 01890