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8 Oak St, Winchester, MA, 01890

5beds
3baths
2,391sqft
$1,125,000
$471price/sqft
$7,308/moest. monthly cost
$292,320/yrincome needed

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

73
WalkingVery Walkable
0
TransitVery Limited Transit
66
BikeBikeable

Schools

9/10
Lynch Elementary SchoolGrades PK-51.0 mi
9/10
McCall Middle SchoolGrades 6-80.6 mi
10/10
Winchester High SchoolGrades 9-120.2 mi

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
    Inland FloodingRelatively High
  • Hurricane
    HurricaneModerate
  • Ice Storm
    Ice StormModerate
  • Tsunami
    TsunamiInsufficient Data

How This Home’s Risks Compare

Inland Flooding
Hurricane
Ice Storm
Tsunami

FEMA Declared Disasters Across Massachusetts Counties

Hurricane

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

MonthlyAnnual
Mortgage $5,688$68,256
Home Insurance *$203$2,436
Property Taxes $946$11,352
Electricity $471$5,657
Total$7,308$87,696
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$250,560/yr
40% on housing$219,240/yr
45% on housing$194,880/yr

Massachusetts FAIR Plan Programs

Massachusetts Property Insurance Underwriting Association

Covered
WildfireWildfire
HailHail
WindWind
Visit Website →
Current Policies
Residential: 213,928Commercial: 230
Total Premiums$400.85M
Total Exposure$115.57B

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.

Insurance Growth Rate5-year average: 7.6%
7.6%
0%30.0%
Electricity Growth Rate10-year average: 7.9%
7.9%
0%15.0%
Property Taxes Growth Rate2-year average: 0.5%
0.5%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$471This listing

vs Other Active Listings

Avg $/sqft

ZIP 01890$514
Middlesex County$437

vs Homes Sold Last Month

Median $/sqft

ZIP 01890$536
Middlesex County$413

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

DateEventPrice
2026-08-11Pending sale$1,125,000
2026-08-06Contingent$1,125,000
2026-07-28Listed for sale$1,125,000

For Sale by Agent

AgentThe Synergy Group
BrokerageThe Synergy Group

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