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Investor alert! About one mile from an array of shops, restaurants, & the commuter rail to Boston, this Winchester multi-family is a rare opportunity waiting to be redesigned! Held by the same family for many years, the property offers substantial square footage & endless potential for those ready to roll up their sleeves. While it requires significant renovation, the reward will be well worth the effort. The classic wood exterior provides timeless character while an addition off the upper level offers valuable extra living space. Each apartment includes fully applianced kitchens & in-unit laundry. Explore the possibilities: convert to a single-family home, pursue a condo conversion, or live in one unit while generating rental income from the other. The main-level unit may be shown at open house only; the upper unit is available for private showings. An exceptional chance to invest in Winchester, known for its top-rated schools, charming neighborhoods, and unbeatable lifestyle!
Current real estate data for Multi Family in Winchester as of Jan 26, 2026
3
Multi Family Listed
341
Avg DOM
369
Avg $ / SqFt
$1,061,667
Avg List Price

Property Details

Price:
$1,025,000
MLS #:
73470713
Status:
Pending
Beds:
6
Baths:
2
Type:
Multi Family
Listed Date:
Jan 21, 2026
Finished Sq Ft:
2,605
Total Sq Ft:
2,605
Lot Size:
7,366 sqft / 0.17 acres (approx)
Year Built:
1926
Units:
2
MccallWinchester High

Schools

Middle School:
Mccall
High School:
Winchester High

Interior

Appliances
Range, Dishwasher, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms
Flooring
Tile, Varies, Hardwood, Parquet
Laundry Features
Washer & Dryer Hookup, Electric Dryer Hookup, Washer Hookup

Exterior

Community Features
Public Transportation
Construction Materials
Frame
Parking Features
Paved Drive, Off Street
Parking Spots
6

Financial

Tax Year
2025
Taxes
$10,669

Map

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Community

Property Summary

    353-355 Washington Street Winchester MA is a Multi Family for sale in Winchester, MA, 01890. It is listed for $1,025,000 To schedule a showing of MLS#73470713 at 353-355 Washington Street in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.

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CRP: Certified Relocation Professional
CRS: Certified Residential Specialist
GRI: Graduate of Realtors Institute
CBR: Certified Buyers Representative
BSBA: Bachelor of Science in Business Administration. Babson College 1979
MBA: Master of Business Administration. Babson College 2002

James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…

More About James
353-355 Washington Street
Winchester, MA