LOCATION! LOCATION! Possibilities abound in this RARE side by side DUPLEX affording popular Townhouse style living in the city- a skip and a jump to the GREEN LINE train, Ball Sq, Davis Square and Tufts University. Long time family owned and occupied cared for home affording you POSSIBILITIES to build sweat equity modernizing. Two level 6/6 2 family home with good bones. Updates include a New roof, gutter & spouts (2025) Addition roof (2020) Both water mains from the street replaced in 2023. Separate Gas furnaces in 2010. Need a first floor bedroom? It's POSSIBLE! Enjoy a nice rear deck and the fenced yard is a perennial paradise. Great property for both investment income and multi generational living. Bakery, restaurants and conveniences at your door- WALK SCORE 97 and BIKERS PARADISE SCORE OF 99. Offers requested by 10am on Monday June 22
| Units | 2 |
| Living area | 2,355 sqft |
| Lot size | 5,054 sqft |
| Year built | 1910 |
| Price / sqft | $408 |
| County | Middlesex |
| MLS # | 73537730 |
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Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
Auto-generated from the listing data — richer AI answers coming with the live site.
It is a 2-unit multi-family property with 2,355 sqft of living area, built in 1910.
At a list price of $988,888 across 2 units, that works out to roughly $494,444 per unit.
At $988,888 for 2,355 sqft, that's about $408 per square foot.
33 Winchester St, Medford MA 02155 is in Medford, Middlesex County, MA 02155.

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.