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.
Multi-familyProperty Type
1910Year Built
4,874 sq ftLot Size
$441Price/Sq.Ft.
4 spacesParking
Listed by The Marrocco Group• Coldwell Banker Realty - Lexington
Winchester Highlands, located between the Middlesex Fells Reservation and Winchester Center, is a residential and wooded Winchester neighborhood with hillside streets and pocket parks. The neighborhood’s character concentrates around the Cambridge Street and Main Street junction, where small storefronts, cafés, and everyday errands cluster in a compact, walkable strip. Book Ends and the Winchester Community Music School act as cultural touchstones, with Wright-Locke Farm adding a seasonal, local-food rhythm nearby. Housing reads as classic New England—Colonial and Cape silhouettes, mature trees, and stone walls along curving roads. Trails and overlooks in the Fells shape the daily backdrop, while the town center’s civic buildings and shops keep the pace grounded.
Provided by Walk Score and Local Logic
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Interior features
Insulated windows
Upgraded countertops
Living room
Dining room
Laundry room
Bathrooms
2 full bathrooms
Bathroom with tub and shower
Kitchen
Range
Dishwasher
Laundry & utility
Washer hookup
Flooring
Wood
Hardwood
Tile
Heating & cooling
Forced-air natural gas heating
Central air conditioning
Exterior features
Fenced yard
Enclosed porch
Wood deck
Rain gutters
Home design
Multi-family property
Two stories
Parking
Four off-street parking spaces
Paved driveway
Construction
Frame construction
Brick and mortar foundation
Shingle roof
Sage exterior
Utilities
Public water
Public sewer
Circuit breakers
HOA & community
Nearby public transportation, shopping, walking and jogging trails, medical facilities, highway access, and public schools
Electricity and solar
View estimated energy costs and solar savings for this home