HomeWinchesterMulti Family8-10 Oak St, Winchester MA 01890
8-10 Oak St, Winchester MA 01890 — photo 1 of 381 / 38
$1,125,000
8-10 Oak St, Winchester MA 01890
2 units · 5 bd · 3 ba · 2,391 sqft · $562,500/unit
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Signal Score pending — we haven't seeded market rents for this ZIP (01890) yet.

About this property

Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

Property details

Units2
Living area2,391 sqft
Lot size4,674 sqft
Year built1870
Price / sqft$471
CountyMiddlesex
MLS #73555245

Listing status

Days on market6 days
Listed onJuly 27, 2026

Taxes & financials

Annual property tax$11,586
Tax year2026
Assessed value$1,045,600
ZoningRG
Total actual rent$0/mo

Building & lot

Stories4
Total rooms11
Lot size0.11 acres
Garage spaces0
Parking spaces3
ParkingPaved Drive, Off Street
BasementFull, Partially Finished
FoundationStone
RoofShingle
ConstructionFrame
FlooringWood, Tile, Vinyl

Utilities & systems

CoolingDuctless
SewerPublic Sewer
WaterPublic
Utilitiesfor Gas Range, for Electric Range
AppliancesRange, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer

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 8-10 Oak St, Winchester MA 01890 have?

It is a 2-unit multi-family property with 2,391 sqft of living area, built in 1870.

How long has 8-10 Oak St, Winchester MA 01890 been on the market?

8-10 Oak St, Winchester MA 01890 has been listed for 6 days (since July 27, 2026).

What is the price per unit?

At a list price of $1,125,000 across 2 units, that works out to roughly $562,500 per unit.

What are the property taxes on 8-10 Oak St, Winchester MA 01890?

Annual property taxes are $11,586 (2026), on an assessed value of $1,045,600.

What is the price per square foot?

At $1,125,000 for 2,391 sqft, that's about $471 per square foot.

Is there parking?

3 total parking spaces (paved drive, off street).

Where is this property located?

8-10 Oak 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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