8 Oak Street, Winchester MA 01890
Track this home for price, status, and open-house alerts.
About this home
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 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 suite is independently served by radiator heat. Outside, a patio and 3 off-street parking spaces complete this exceptional property. The location is a commuter's dream, situated just a short stroll to vibrant Winchester Center, boutique shops, local cafés, and acclaimed restaurants. Commuters will love being near 2 MBTA Commuter Rail stations, offering a quick 2-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.
View in the App
Save this property, schedule tours instantly, and get alerts when the price drops
Scan with phone
Public Records & Permits
Log in to view assessor & tax records, ownership history, and recent building permits for this property.
BMN Estimate
Get the number an algorithm can't give you
A free agent CMA factors in condition, upgrades, and the street — the things comps alone can't see.
Recently Sold Nearby
Property History
Market Insights
Property Timeline
Status: Active under contract
Aug 6, 2026Pending Sale
Aug 6, 2026Listed for Sale
Jul 28, 2026| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 08/06/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 08/06/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 07/28/2026 | 🏠 Listed for Sale | $1,125,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $11,586 | $1,045,600 |
Financial Details
Facts & Features
Home Facts
Interior
Exterior
Parking
Utilities
Financial
HOA & Community
MA Disclosures
Additional Details
Property Overview
Floor Layout
Floor Layout
Finished Area
Display Options
Outdoor Areas
Room Markers
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Construction & Materials
Heating, Cooling & Utilities
Exterior & Lot
Parking & Garage
Nearby Schools
School information not available for this location.
Monthly Payment Calculator
Monthly Payment Breakdown
Loan Summary
Rate Impact
Payment Over Time
Location
Neighborhood
8 Oak Street, Winchester MA 01890
Winchester, MA 01890
Listing Information
Contact Us
Similar Homes for Sale
Comparable Properties
Customize Comparable Search
Finding comparable properties...
