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8 Oak Street, Winchester MA 01890

$1,125,000

Estimated $7,897/month Calculator

Single Family

5 Bedrooms

Baths

2391

Total Parking: 3

4,674 (0.11)

Built in 1870

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.

This home has been viewed 2 times

Last Checked: July 28th, 2026 at 7:43pm (Source: MLS PIN #73555597)

Air Conditioning

Lead Paint Free

General Information for 8 Oak Street, Winchester MA 01890

Listing ID73555597

Property TypeSingle Family / Detached

Price$1,125,000 ($470.51/SqFt)

StyleColonial

CityWinchester

CountyMiddlesex

Neighborhood(s)

Garage Parking0

ZoningRG

Year Built1870

Year Built SourcePublic Records

Year Built DetailsActual

Interior Features for 8 Oak Street, Winchester MA 01890

Approximate Living Area Total2391

Living Area Includes BasementYes

Rooms11

Bedrooms5

Primary En Suite BathroomYes

BasementFull

Cooling1, Split

Fireplaces

AppliancesRange

FlooringTile

Electric

Exterior Features for 8 Oak Street, Winchester MA 01890

Approximate Lot Size (Acres)0.11

Approximate Lot Size (Square Feet)4674

Total Parking3

Garage Parking0

WaterPublic

SewerPublic Sewer

Lot FeaturesGentle Sloping

Parking Features1

Exterior FeaturesPorch

Foundation Materials

Construction MaterialsFrame

Road Frontage Type

Patio & PorchCovered

Roof MaterialAsphalt/fiberglass Shingles

Utility Connections110 Volts

Water Views

Water Views Features

Waterfront0

Waterfront Features

Pool Features

Horse Permitted0

Horse Amenities

Disclosures for 8 Oak Street, Winchester MA 01890

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourceMeasured

Special Listing Conditions

ExclusionsElectric Fireplace

Compensation Based On

Financial Information for 8 Oak Street, Winchester MA 01890

Association Fee

Association Fee Frequency

Association Fee Includes

Real Estate Tax11586

Tax Year2026

Assessed Value$1,045,600

Location Information for 8 Oak Street, Winchester MA 01890

Elementary SchoolLynch Elementary School

Middle SchoolMccall Middle School

High SchoolWinchester Highschool

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 8 Oak Street, Winchester MA 01890

Agent

Name: The Synergy Group

Office

Name: The Synergy Group

Phone: 888-410-5454

Team Members

Payment Calculator

, Interest

Property Taxes 965.5

Principal & Interest 6931.89

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

The Synergy Group

Agent Phone

Office Phone

(888) 410-5454

Text Agent Call Agent Call Office

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EXIT

35 More Photos

Active

8 Oak Street, Winchester MA 01890

$1,125,000

General Information for 8 Oak Street, Winchester MA 01890

Interior Features for 8 Oak Street, Winchester MA 01890

Exterior Features for 8 Oak Street, Winchester MA 01890

Disclosures for 8 Oak Street, Winchester MA 01890

Financial Information for 8 Oak Street, Winchester MA 01890

Location Information for 8 Oak Street, Winchester MA 01890

Contact Information for 8 Oak Street, Winchester MA 01890

Agent

Office

Team Members

Payment Calculator

Exclusive Listing Agent

The Synergy Group

The Synergy Group