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
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
Contact Us
Mortgage Calculator
Community
- Address353-355 Washington Street Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Close to Wright Locke Farm
- Cox Road / High St Extension neighborhood
- East SIde near town forest!!
- Everett/ Stratford
- Flats location
- FLATS location Across from Wedgemere/Oxford
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Ledgewood Estates
- Middlesex
- Myopia Hill/ Winchester Country Club Area
- Near VO school
- old village/ West side
- The Flats
- Top neighborhood near town center
- West side
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 JamesCourtesy of Gibson Sotheby’s International Realty. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
353-355 Washington Street
Winchester, MA
































