8-10 Oak St, Winchester, MA 01890

• 5 beds |
• 3 baths |
• 2,391 sqft

Property Description

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.

Listing Status:

Active

Date Added:

July 27, 2026

Data Last Updated:

August 6, 2026 at 7:08AM

Listing Office:

The Synergy Group : 888-410-5454

Listing Agent:

The Synergy Group : 781-570-9007

MLS ID:

73555245

Interior

• General: Stone/Granite/Solid CountersBathroom With Tub & ShowerOpen FloorplanRemodeledSliderLiving RoomDining RoomKitchenFamily Room
• Appliances: RangeDishwasherDisposalMicrowaveRefrigeratorWasherDryer
• Basement: FullPartially Finished
• Flooring: WoodTileVinyl
• A/C: Ductless
• Fireplace: Fireplaces: 0

Exterior

• General: Balcony/Deck
• Parking: Paved DriveOff StreetParking spaces: 3

Construction

• Roofing: Shingle
• Windows: Insulated Windows
• General: Frame4Stone

Location

• Road/Access: Public
• Originating MLS: MLS Property Information Network
• County: Middlesex

Lot

• Zoning: RG897000
• Fencing: Fenced/EnclosedFenced

Utilities

• Utilities: for Gas Rangefor Electric Range
• Water: Public
• Sewer: Public Sewer

Financial

• Source: MLS Property Information Network