8 Oak Street Winchester MA 01890 | MLS #73555597

8 Oak Street
Winchester, MA, 01890
$1,125,000
5 Beds
2.5 Baths
2,391 SqFt
0.11 Acres
$1,125,000
8 Oak Street
Winchester, MA, 01890
MLS #73555597 image #0
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 cafĂ©s, 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.

Property Details

Price:
$1,125,000
MLS #:
73555597
Status:
Pending
Beds:
5
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Jul 28, 2026
Finished Sq Ft:
2,391
Total Sq Ft:
2,391
Lot Size:
4,674 sqft / 0.11 acres (approx)
Year Built:
1870
FarmhouseLynch Elementary SchoolMccall Middle SchoolWinchester Highschool

Schools

Elementary School:
Lynch Elementary School
Middle School:
Mccall Middle School
High School:
Winchester Highschool

Interior

Above Grade Finished Area
2091
Appliances
Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
300
Cooling
Ductless
Flooring
Wood, Tile, Vinyl, Flooring – Vinyl, Flooring – Wood
Heating
Baseboard, Hot Water, Ductless
Interior Features
Bathroom – With Tub & Shower, Closet, Dining Area, Lighting – Overhead, Accessory Apt.
Laundry Features
In Basement

Exterior

Architectural Style
Farmhouse
Community Features
Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Highway Access, House of Worship, Public School, Sidewalks
Construction Materials
Frame
Exterior Features
Porch, Deck, Patio, Fenced Yard
Fencing
Fenced/Enclosed, Fenced
Lot Features
Level
Open Parking Spaces
3
Open Parking YN
1
Parking Features
Paved Drive, Off Street, Paved
Parking Spots
3
Parking Total
3
Patio And Porch Features
Porch, Deck, Patio
Roof
Shingle
Window Features
Insulated Windows

Financial

Tax Year
2026
Taxes
$11,586
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Marie Andrews

Marie Andrews

Realtor®, Broker/Owner, GBREB, Notary Public

Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…

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Map

Current real estate data for Single Family in Winchester as of Sep 21, 2026
60
Single Family Listed
61
Avg DOM
561
Avg $ / SqFt
$1,945,328
Avg List Price

Community

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Property Summary

    8 Oak Street Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $1,125,000 and features 5 beds, 3 baths, and has approximately 2,391 square feet of living space, and was originally constructed in 1870. The current price per square foot is $471. The average price per square foot for Single Family listings in Winchester is $561. The average listing price for Single Family in Winchester is $1,945,328. To schedule a showing of MLS#73555597 at 8 Oak Street in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
8 Oak Street
Winchester, MA