$1,125,000
8 Oak Street
Winchester, MA, 01890
OH 7/31 4-5pm, 8/1 & 8/2 12-1:30pm 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:
Active
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
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
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 Jul 31, 2026
59
Single Family Listed
67
Avg DOM
557
Avg $ / SqFt
$1,993,317
Avg List Price
Community
- Address8 Oak Street Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
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 $557. The average listing price for Single Family in Winchester is $1,993,317. To schedule a showing of MLS#73555597 at 8 Oak Street in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of The Synergy Group. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
8 Oak Street
Winchester, MA









































