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.
| Units | 2 |
| Living area | 2,391 sqft |
| Lot size | 4,674 sqft |
| Year built | 1870 |
| Price / sqft | $471 |
| County | Middlesex |
| MLS # | 73555245 |
| Days on market | 6 days |
| Listed on | July 27, 2026 |
| Annual property tax | $11,586 |
| Tax year | 2026 |
| Assessed value | $1,045,600 |
| Zoning | RG |
| Total actual rent | $0/mo |
| Stories | 4 |
| Total rooms | 11 |
| Lot size | 0.11 acres |
| Garage spaces | 0 |
| Parking spaces | 3 |
| Parking | Paved Drive, Off Street |
| Basement | Full, Partially Finished |
| Foundation | Stone |
| Roof | Shingle |
| Construction | Frame |
| Flooring | Wood, Tile, Vinyl |
| Cooling | Ductless |
| Sewer | Public Sewer |
| Water | Public |
| Utilities | for Gas Range, for Electric Range |
| Appliances | Range, Dishwasher, Disposal, Microwave, Refrigerator, Washer, Dryer |
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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 2,391 sqft of living area, built in 1870.
8-10 Oak St, Winchester MA 01890 has been listed for 6 days (since July 27, 2026).
At a list price of $1,125,000 across 2 units, that works out to roughly $562,500 per unit.
Annual property taxes are $11,586 (2026), on an assessed value of $1,045,600.
At $1,125,000 for 2,391 sqft, that's about $471 per square foot.
3 total parking spaces (paved drive, off street).
8-10 Oak 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.