8 Oak Street, Winchester MA 01890

Winchester, MA 01890
$1,125,000
Est. $6,854/month
5
Beds
2.5
Baths
2,391
Sq Ft
$471
Price/Sq Ft
0.11
Acres
1870
Year Built
3
Parking
13
Days on Market
Sale Pending Listed Jul 28, 2026 • MLS# 73555597 Copied! • Updated Aug 11, 2026

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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.

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Recently Sold Nearby

Property History

Market Insights

Property Timeline

📋
Status: Active under contract
Aug 6, 2026
Active → Active Under Contract
Pending Sale
Aug 6, 2026
Offer accepted, sale pending
🏠
Listed for Sale
Jul 28, 2026
$1,125,000
Original listing
Agent: The Synergy Group Office: The Synergy Group

Tax History

Year Taxes Assessment
2026 $11,586 $1,045,600

Financial Details

Annual Property Tax
$11,586
Tax Year 2026
Assessed Value
$1,045,600

Facts & Features

Home Facts

Type Residential
Style Single Family Residence
Year Built 1870
Living Area 2,391 sq ft
Lot Size 0.11 acres
Bedrooms 5
Full Baths 2
Half Baths 1
Total Rooms 11

Interior

Heating Baseboard, Hot Water, Ductless
Cooling Ductless
Flooring Wood, Tile, Vinyl, Flooring - Vinyl, Flooring - Wood
Appliances Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Fireplace None
Basement Full, Partially Finished
Laundry In Basement
Features Bathroom - With Tub & Shower, Closet, Dining Area, Lighting - Overhead, Accessory Apt.

Exterior

Construction Frame
Architecture Farmhouse
Roof Shingle
Features Porch, Deck, Patio, Fenced Yard
Pool None
Spa None
Fencing Fenced/enclosed, Fenced
Patio/Porch Porch, Deck, Patio
Features Paved Drive, Off Street, Paved
Total Spaces 3
Electric None
Water Public
Sewer Public Sewer
Gas None
Other For Gas Range, For Electric Range
Annual Tax $11,586
Assessed Value $1,045,600
Fee Includes None
Amenities None
Optional Fee Includes None
Seller Disclosures Entire Home To Be Delivered Vacant. Seller Prefers Closing Sept 28. 2 Sides Of Fascia Boards On Front Porch Need Replacing. Offers Due Mon, 8/3 By 12pm - One Pdf To Marie. Main Home Pays All Heat & Water. Accessory Apt Pays Its Own Electric.
Possession None
Accepted Financing None
Structure Type []
House Color Yellow
Sq Ft Source Measured
Sq Ft Disclosures Floor plans measurements are approximate. Buyer and Buyers agent to do their own due diligence.
Documents None
County Middlesex
Total market time (incl. prior listings) 14 days

Property Overview

Property Type
Single Family Residence
Listing Type
Sale Pending
Year Built
1870
Bedrooms
5
Full Bathrooms
2
Half Bathrooms
1
Living Area
2,391 sq ft
Total Rooms
11

Floor Layout

Interior Features

Flooring: Wood, Tile, Vinyl, Flooring - Vinyl, Flooring - Wood
Appliances: Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Interior Features: Bathroom - With Tub & Shower, Closet, Dining Area, Lighting - Overhead, Accessory Apt.
Windows: Insulated Windows
Basement: Full, Partially Finished
Laundry: In Basement
Security:

Construction & Materials

Style: Farmhouse
Year Built: 1870
Structure Type:
Exterior Materials: Frame
Roof: Shingle
Foundation: Stone

Heating, Cooling & Utilities

Heating: Baseboard, Hot Water, Ductless
Cooling: Ductless
Hot Water:
Water Source: Public
Sewer: Public Sewer
Energy Features:

Exterior & Lot

Exterior Features: Porch, Deck, Patio, Fenced Yard
Patio & Porch: Porch, Deck, Patio
Fencing: Fenced/Enclosed, Fenced
Other Structures:
Lot Features: Level
Road Surface: Paved

Parking & Garage

Total Parking Spaces: 3
Parking Features: Paved Drive, Off Street, Paved

Nearby Schools

School information not available for this location.

Monthly Payment Calculator

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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $966
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Location

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Neighborhood

8 Oak Street, Winchester MA 01890

Winchester, MA 01890

Listing Information

Listing Agent The Synergy Group
Listing Office The Synergy Group
Office Phone 888-410-5454
Agent MLS ID TM321745
Office MLS ID AN7316
Listing Data Updated Aug 11, 2026 9:19 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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Steve Novak Real Estate
Steve Novak Real Estate
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