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Lauren Chadwick
REALTOR®
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8 Oak Street, Winchester, MA 01890

$1,125,000
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New to the Market Active
BEDS5 BATHS2 full 1 partial SQUARE FEET2,391 MLS#73555597
STATUSActive PROPERTY TYPEResidential - Single Family

Property Description

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.

8 Oak Street | MLS# 73555597

This single family home located at 8 Oak Street, Winchester, MA 01890 is currently listed for sale with an asking price of $1,125,000. This property was built in 1870 and has 5 bedrooms and 2 full and 1 partial baths with 2391 sq. ft. Search Winchester real estate on laurenchadwick.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Full, Partially Finished
Basement: Yes
Cooling: Ductless
Fenced: Yes
Heating: Baseboard, Hot Water, Ductless
Home Style: Farmhouse
Lot Size: 0.11 Acres
Roof Type: Shingle
Taxes: $11,586
Year Built: 1870

Amenities

Bathroom - With Tub & Shower
Closet
Dining Area
Lighting - Overhead
Accessory Apt.
Porch
Deck
Patio
Fenced Yard

Feature Descriptions

Appliances: Range, Dishwasher, Disposal, Refrigerator, Washer, Dryer
Building Area Total: 2391
Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Medical Facility, Highway Access, House of Worship, Public School, Sidewalks
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 1
Dining Room: Flooring - Wood, Open Floorplan, Lighting - Overhead
Door Features: Insulated Doors
Exterior: Frame
Family Room: Lighting - Overhead
Fencing: Fenced/Enclosed, Fenced
Flooring: Wood, Tile, Vinyl, Flooring - Vinyl, Flooring - Wood
HeatingY/N: 1
Kitchen: Flooring - Wood, Countertops - Stone/Granite/Solid, Kitchen Island
Laundry: In Basement
Living Room: Flooring - Wood, Open Floorplan, Lighting - Overhead
Lot Features: Level
Master Bedroom: Closet, Flooring - Wood, Lighting - Overhead
Open Parking Y/N: Yes
Parcel Number: 897000
Parking Features: Paved Drive, Off Street, Paved
Parking Total: 3
Patio And Porch: Porch, Deck, Patio
Road Responsibility: Public Maintained Road
Rooms Total: 11
Sewer: Public Sewer
Utilities: for Gas Range, for Electric Range
Water: Public
Window Features: Insulated Windows

Room Sizes

Bathroom 1: 7.00 X 3.00 Level - First
Bathroom 2: 11.00 X 5.00 Level - Second
Bedroom 2: 13.00 X 9.00 Level - Second
Bedroom 3: 16.00 X 10.00 Level - Second
Bedroom 4: 16.00 X 12.00 Level - First
Dining Room: 12.00 X 8.00 Level - First
Family Room: 18.00 X 17.00 Level - Basement
Kitchen: 14.00 X 12.00 Level - First
Living Room: 22.00 X 12.00 Level - First
Primary Bedroom: 12.00 X 11.00 Level - Second

Local Schools

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

Listed By / Shown By

Listed By

Agency Name: The Synergy Group
Agent Name: The Synergy Group
Agency Phone: 888-410-5454

Shown By

Agent Name: Lauren Chadwick
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 3,797.39 per month $2,503.76 Principal & Interest $965.50 Property Tax $328.13 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 07/29/2026. The listing information on this page last changed on 07/29/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 07/29/2026 12:00:27 AM EST) or MLSPIN MLS (last updated Tue 07/28/2026 11:38:25 PM EST) or Prime MLS (last updated Tue 07/28/2026 11:33:34 PM EST) or MREIS (last updated Tue 07/28/2026 11:55:14 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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