HomeWinchesterMulti Family257 Cross St, Winchester MA 01890
257 Cross St, Winchester MA 01890 — photo 1 of 391 / 39
$1,099,000
257 Cross St, Winchester MA 01890
2 units · 5 bd · 3 ba · 2,801 sqft · $549,500/unit
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INVESTMENT SNAPSHOT

Signal Score pending — we haven't seeded market rents for this ZIP (01890) yet.

About this property

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!

Property details

Units2
Living area2,801 sqft
Lot size10,367 sqft
Year built1960
Price / sqft$392
CountyMiddlesex
MLS #73553083

Listing status

Days on market10 days
Listed onJuly 21, 2026

Taxes & financials

Annual property tax$9,849
Tax year2025
Assessed value$888,100
ZoningRG
Total actual rent$0/mo

Building & lot

Stories2
Total rooms11
Lot size0.24 acres
Garage spaces0
Parking spaces4
BasementFull, Finished, Walk-Out Access
FoundationConcrete Perimeter
RoofShingle

Utilities & systems

HeatingOil
CoolingCentral Air
SewerPublic Sewer
WaterPublic

Location

More about investing in Winchester

Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.

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Questions & answers

Auto-generated from the listing data — richer AI answers coming with the live site.

How many units does 257 Cross St, Winchester MA 01890 have?

It is a 2-unit multi-family property with 2,801 sqft of living area, built in 1960.

How long has 257 Cross St, Winchester MA 01890 been on the market?

257 Cross St, Winchester MA 01890 has been listed for 10 days (since July 21, 2026).

What is the price per unit?

At a list price of $1,099,000 across 2 units, that works out to roughly $549,500 per unit.

What are the property taxes on 257 Cross St, Winchester MA 01890?

Annual property taxes are $9,849 (2025), on an assessed value of $888,100.

What is the price per square foot?

At $1,099,000 for 2,801 sqft, that's about $392 per square foot.

Is there parking?

4 total parking spaces.

Where is this property located?

257 Cross St, Winchester MA 01890 is in Winchester, Middlesex County, MA 01890.

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Justin Rollo, Broker Associate at Signal Real Estate
Justin RolloBroker Associate, Signal Real Estate · MA Lic. #9534264

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.

📞 978-790-4381📍 25 Braintree Hill Park, Suite 200, Braintree, MA 02184
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