Exceptional two-family opportunity with incredible potential to renovate/expand! Situated on a large, level corner lot with frontage on both Cross Street and Verplast Avenue, this property offers endless possibilities for investors, builders, or owner-occupants. The first-floor unit features a fireplaced living room, an updated kitchen, three bedrooms, 1.5 baths and sunroom overlooking the expansive backyard. The second unit offers a spacious and flexible layout with a living room, kitchen, 2 bedrooms, laundry room and full bath. The generous lot, separate entrances, and existing footprint create an ideal opportunity to modernize the current two-family, expand the living space, or explore redevelopment possibilities. Whether you're looking for a strong income property or your next renovation project, this property is full of potential and ready for its next chapter!
| Units | 2 |
| Living area | 2,801 sqft |
| Lot size | 10,367 sqft |
| Year built | 1960 |
| Price / sqft | $392 |
| County | Middlesex |
| MLS # | 73553083 |
| Days on market | 10 days |
| Listed on | July 21, 2026 |
| Annual property tax | $9,849 |
| Tax year | 2025 |
| Assessed value | $888,100 |
| Zoning | RG |
| Total actual rent | $0/mo |
| Stories | 2 |
| Total rooms | 11 |
| Lot size | 0.24 acres |
| Garage spaces | 0 |
| Parking spaces | 4 |
| Basement | Full, Finished, Walk-Out Access |
| Foundation | Concrete Perimeter |
| Roof | Shingle |
| Heating | Oil |
| Cooling | Central Air |
| Sewer | Public Sewer |
| Water | Public |
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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 2,801 sqft of living area, built in 1960.
257 Cross St, Winchester MA 01890 has been listed for 10 days (since July 21, 2026).
At a list price of $1,099,000 across 2 units, that works out to roughly $549,500 per unit.
Annual property taxes are $9,849 (2025), on an assessed value of $888,100.
At $1,099,000 for 2,801 sqft, that's about $392 per square foot.
4 total parking spaces.
257 Cross St, Winchester MA 01890 is in Winchester, Middlesex County, MA 01890.

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.