Sold Sep 8, 2026
$1,340,000Upcoming open house
Sat, Nov 7 · 12:00 PM–1:00 PM
Arrive prepared. Get the November 2026 Winchester Bean Group Buyer’s Guide before you tour.
About this home
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.
Listing last checked: Listing updated:
Listed by The Marrocco Group · Coldwell Banker Realty - Lexington · MLS #73592723
Request property information
Select a document to start a request. You can add others in the form. Availability varies.
Details at a glance
Interior5 property facts
- Rooms
- 12
- Heating
- Forced Air, Natural Gas, Electric
- Cooling
- Central Air
- Flooring
- Wood, Vinyl
- Basement
- Yes · Unfinished
Building5 property facts
- Style
- Multi Family
- Year built
- 1910
- Parking
- 4
- Foundation
- Stone, Other
- Roof
- Shingle
Land & utilities5 property facts
- Lot size
- 0.11 acres
- Water
- Public
- Sewer
- Public Sewer
- Pool
- Not reported
- Zoning
- RG
Financial2 property facts
- Annual taxes
- $10,670
- Assessment year
- 2026
Location
Estimated monthly cost
Explore costs at the $1,249,000 asking price. Adjust the assumptions to your situation.
Known monthly costs$7,205 / monthAdjust
- Principal & interest
- $6,316
- Property tax
- $889
- Insurance
- Not entered
- HOA
- Not entered
Listing annual taxes: $10,670. 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.
More property insights
Automated value estimate $1,317,016
Estimated range $1,257,385–$1,376,647.
Automated estimates are not appraisals or guarantees of market value.
Request a professional market analysisComparable properties 1 supplied
Photo-based condition insights
Overall presentation: average
Explore more of Winchester
Continue your search in Winchester.
Need help making sense of this home?
About 419-421 Washington St
Can I request a private showing?
Request a tour of 419-421 Washington St and a Bean Group agent will help coordinate an available time with the listing side.
Can you help me evaluate this property?
Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.
Are property documents available?
Availability varies by property and source. Request the documents you need and we will help obtain what is available.