An exceptional turnkey opportunity in Winchester, 419–421 Washington Street presents a beautifully refreshed two-family residence featuring significant mechanical upgrades and refined finishes throughout. Major improvements include a brand-new roof, newly paved driveway with parking for 4–5 vehicles, separate central heating and air conditioning systems, separate utilities, fresh interior and exterior paint, and beautifully refinished hardwood floors. Ideally situated near vibrant Winchester Center, enjoy convenient access to local dining, boutique shopping and commuter rail service to Boston. Proximity to Winchester Hospital, I-93, Route 128/I-95, Middlesex Fells Reservation and Winchester's highly regarded schools further enhances the appeal. Move-in ready with extensive recent improvements, this exceptional property offers an ideal opportunity for owner-occupants and investors seeking lasting value in one of Greater Boston's most desirable communities.
419-421 Washington St, Winchester MA 01890
Winchester, MA 01890
- Property type
- Multi Family
- Status
- Active
- Year built
- 1910
- Lot size
- 0.11 acres
- Living area
- 2,946 sf
- MLS#
- c77a232a1e2ace7001b0162af8c22ed5
- Beds · Baths
- 6 · 2
Winchester, MA.
Winchester, Massachusetts, is a market our advisors follow closely — its streets, housing stock and setting each shape what a residence here is worth and how it lives day to day. We are glad to walk you through the locale in detail, and how this particular address sits within it.
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Listings updated Oct 24, 2026



