8 Oak StreetWinchester, MA 01890MLS Number 73555597

  • Price: $1,125,000
  • Est. Mortgage of $/month
  • 2 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.58% last updated on Jul 23, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
Open House
8 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 018908 Oak Street Winchester MA 01890
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  • 5Bedrooms
  • 0.11Acreage
  • 3Bathrooms
  • 1870Year Built

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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 cafs, 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.

Open Houses

August 1st
Starts: 12:00pm
Ends: 1:30pm
August 2nd
Starts: 12:00pm
Ends: 1:30pm
Listed by The Synergy Group of The Synergy Group

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More Info

Basic Information

  • Bedrooms5
  • Mls StatusNew
  • Bathroom3
  • Lot Features Level
  • Parcel Number 897000
  • Road Frontage DescriptionPaved

Basic Information

  • List Price$1,125,000
  • MLS Number73555597
  • Modification Date07/28/2026
  • Property SubTypeSingle Family Residence

Building

  • BasementFull, Partially Finished
  • Building Area Units Square Feet
  • Construction Materials Frame
  • Door Features Insulated Doors
  • FoundationStone
  • Patio And Porch Features Porch, Deck, Patio
  • Property StyleFarmhouse
  • Rooms11
  • Utilities For Gas Range, For Electric Range
  • Window Features Insulated Windows
  • Year Built1870
  • Year Built Details Actual
  • Year Built Source Public Records

Amenities

  • Amenities
    • Highway Access
    • House of Worship
    • Medical Facility
    • Park
    • Public School
    • Public Transportation
    • Shopping
    • Sidewalks
    • Walk/Jog Trails
  • Appliances IncludedRange, Dishwasher, Disposal, Refrigerator, Washer, Dryer

Tax Information

  • Tax Assessed Value $1,045,600
  • Tax Year 2026
  • Taxes$11,586

Parking

  • Parking Spaces3
  • Open Parking YN Yes
  • Parking Features Paved Drive, Off Street, Paved

Location

  • Address8 Oak Street
  • Building Number8
  • CountyMiddlesex
  • StateMA
  • StreetOak Street
  • TownWinchester
  • Zip01890

Property

  • Acreage0.11

Interior

  • Flooring Wood, Tile, Vinyl, Flooring - Vinyl, Flooring - Wood
  • Interior Features Bathroom - With Tub & Shower, Closet, Dining Area, Lighting - Overhead, Accessory Apt.

Utilities

  • Cooling Ductless
  • Cooling YN Yes
  • Heat SystemYes
  • Heating Baseboard, Hot Water, Ductless
  • Sewer Public Sewer
  • Water Source Public

Other

  • Date Listed07/28/2026
  • Farm Land Area Units Square Feet

School Information

  • High School Winchester Highschool
  • Elementary SchoolLynch Elementary School
  • Junior HighMccall Middle School

Rooms

  • Bathroom 1 First,7 x 3
  • Bathroom 2 Second,11 x 5
  • Bathrooms Total Decimal 2.5
  • Bedroom 2 Second,13 x 9
  • Bedroom 3 Second,16 x 10
  • Bedroom 4 First,16 x 12
  • Dining Room First,12 x 8
  • Family Room Basement,18 x 17
  • Full Bath2
  • Half Baths1
  • Kitchen First,14 x 12
  • Living Room First,22 x 12
  • Master Bedroom Second,12

Exterior

  • Exterior Features Porch, Deck, Patio, Fenced Yard
  • Fencing Fenced/Enclosed, Fenced
  • RoofShingle

Property Information

  • Square Feet2,391
  • Building Area Source Measured
  • Living Area 2,391
  • Lot Size Square Feet 4,674
  • Lot Size Units Acres
  • Road Responsibility Public Maintained Road
CENTURY 21 Shawmut Properties | Brighton
CENTURY 21 Shawmut Properties | Brighton
134 Tremont Street
Brighton, MA 02135

Winchester, MA Demographics

There is no data available

Winchester, MA Real Estate Market Data

There is no data available

Winchester, MA Schools

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The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. The property listing data and information, and the Images, 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. MLSPIN and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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