




8 Oak St, Winchester, MA, 01890
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.
Getting Around
Schools
Construction
Condition
- Year built: 1870
Materials
- Foundation: Stone
- Roof: Shingle
- Construction materials: Frame
Type & Style
- Home type: SingleFamily
- Architectural style: Farmhouse
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Range,Dishwasher,Disposal,Refrigerator,Washer,Dryer
- Laundry features: In Basement
Basement
- Has basement: Yes
- Basement: Full,Partially Finished
Bathroom1
- Features: Bathroom - Half
- Level: First
- Area: 21
Bathroom2
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Lighting - Pendant
- Level: Second
- Area: 55
Bedroom2
- Features: Closet, Lighting - Overhead
- Level: Second
- Area: 117
Bedroom3
- Features: Closet, Lighting - Overhead
- Level: Second
- Area: 160
Bedroom4
- Features: Closet, Flooring - Wood, Lighting - Overhead
- Level: First
- Area: 192
Bedrooms & Bathrooms
- Bedrooms: 5
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Dining Room
- Features: Flooring - Wood, Open Floorplan, Lighting - Overhead
- Level: First
- Area: 96
Family Room
- Features: Lighting - Overhead
- Level: Basement
- Area: 306
Features
- Bathroom - With Tub & Shower,Closet,Dining Area,Lighting - Overhead,Accessory Apt.
- Door features: Insulated Doors
- Window features: Insulated Windows
- Flooring: Wood,Tile,Vinyl,Flooring - Vinyl,Flooring - Wood
- Finished area below ground: 300
- Finished area above ground: 2,091
Heating & Cooling
- Heating features: Baseboard,Hot Water,Ductless
- Cooling features: Ductless
Interior Area
- Total structure area: 2,391
- Total interior livable area: 2,391 sqft
Kitchen
- Features: Flooring - Wood, Countertops - Stone/Granite/Solid, Kitchen Island
- Level: First
- Area: 168
Living Room
- Features: Flooring - Wood, Open Floorplan, Lighting - Overhead
- Level: First
- Area: 264
Master Bedroom
- Features: Closet, Flooring - Wood, Lighting - Overhead
- Level: Second
- Area: 132
Property
Details
- Parcel number: 897000
- Zoning: RG
Features
- Patio & porch: Porch,Deck,Patio
- Exterior features: Porch,Deck,Patio,Fenced Yard
- Fencing: Fenced/Enclosed,Fenced
Lot
- Lot size: 4,674 sqft
- Features: Level
Parking
- Total spaces: 3
- Parking features: Paved Drive,Off Street,Paved
- Has uncovered spaces: Yes
- Uncovered spaces: 3
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Inland Flooding
- Hurricane
- Ice Storm
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters Across Massachusetts Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $5,688 | $68,256 |
| Home Insurance * | $203 | $2,436 |
| Property Taxes | $946 | $11,352 |
| Electricity | $471 | $5,657 |
| Total | $7,308 | $87,696 |
Income You'd Need if You Spent...
Massachusetts FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
No zestimate history available
Price History
| Date | Event | Price |
|---|---|---|
| 2026-08-11 | Pending sale | $1,125,000 |
| 2026-08-06 | Contingent | $1,125,000 |
| 2026-07-28 | Listed for sale | $1,125,000 |
