8 Oak Street, Winchester, MA 01890

• 5 beds |
• 3 baths |
• 2,391 sqft

Property Description

Thoughtfully updated 1870 home with a versatile footprint offering many options for multi-generational living, a grand home office setup, dedicated au pair quarters, or separately rented as an Accessory Dwelling Unit (ADU). Elegant renovations have preserved the home's original historic character while seamlessly incorporating today's modern luxuries. A charming farmer's porch welcomes you into the main living area, featuring 8 rooms, 4 bedrooms, and 1.5 baths. The beautifully renovated 2024 eat-in kitchen showcases timeless cabinetry, quartz countertops, a functional butcher block island, custom blue-and-white tile backsplash, an exterior-vented gas range, and direct access to a new 2024 TimberTech deck. Interior highlights include an inviting living room with a striking embossed tin ceiling, a flexible first-floor bedroom or office featuring floor-to-ceiling windows, and gorgeous wide-plank flooring. The walk-out lower-level family room adds excellent bonus space with direct access to the backyard, while three additional bedrooms sit on the second floor. The full bath was tastefully renovated in 2020 with vintage-inspired washstand sinks, and the unfinished basement provides laundry space and storage. The separate, fully integrated living area is ideal for extended family, guests, an au pair, or rental income. This bright secondary suite offers a sunlit living room with its own deck access, an eat-in kitchen, full bath, and a spacious second-floor bedroom. Original pine floors on main level and carpet in bedroom. Modern mini-split heating and A/C units provide year-round climate control throughout both distinct living areas. The main home also features gas baseboard and radiator heat, while the suite is independently served by radiator heat. Outside, a patio and three off-street parking spaces complete this exceptional property. The location is an absolute commuter's dream, situated just a short stroll to vibrant Winchester Center, boutique shops, local cafés, and acclaimed restaurants. Commuters will love being near two MBTA Commuter Rail stations, offering a quick two-stop ride straight into Boston's North Station. Best of all, this property sits within the highly sought-after Lynch Elementary School district, placing you directly inside Winchester's top-rated, award-winning public school system. This rare property truly offers the perfect combination of timeless historic charm, high-end modern updates, and outstanding lifestyle versatility.

Listing Status:

Active

Date Added:

July 28, 2026

Data Last Updated:

July 29, 2026 at 5:08AM

Listing Office:

The Synergy Group : 888-410-5454

Listing Agent:

The Synergy Group : 781-570-9007

MLS ID:

73555597

Interior

• General: Bathroom - With Tub & ShowerClosetDining AreaLighting - OverheadAccessory Apt.
• Appliances: RangeDishwasherDisposalRefrigeratorWasherDryer
• Laundry: In Basement
• Basement: FullPartially Finished
• Flooring: WoodTileVinylFlooring - VinylFlooring - Wood
• A/C: Ductless
• Heating: BaseboardHot WaterDuctless
• Fireplace: Fireplaces: 0

Exterior

• General: PorchDeckPatioFenced Yard
• Style: Farmhouse
• Parking: Paved DriveOff StreetPavedParking spaces: 3

Construction

• Roofing: Shingle
• Windows: Insulated Windows
• General: FrameStone

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