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Annalise Hardy
REALTOR®
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8-10 Oak St, Winchester, MA 01890

$1,125,000
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New to the Market Active
BEDS5 BATHS2 full 1 partial SQUARE FEET2,391 MLS#73555245
STATUSActive PROPERTY TYPEMulti Unit - Multiple

Property Description

Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

8-10 Oak St | MLS# 73555245

This multi-family property located at 8-10 Oak St, Winchester, MA 01890 is currently listed for sale with an asking price of $1,125,000. Search Winchester real estate on annalisehardy.masiellogrouprealestate.com today.

Property Features

Property Type: Multi Unit - Multiple
Basement: Full, Partially Finished
Basement: Yes
Cooling: Ductless
Fenced: Yes
Lot Size: 0.11 Acres
Roof Type: Shingle
Stories: 4.0
Taxes: $11,586
Year Built: 1870

Amenities

Stone/Granite/Solid Counters
Bathroom With Tub & Shower
Open Floorplan
Remodeled
Slider
Living Room
Dining Room
Kitchen
Family Room
Balcony/Deck

Feature Descriptions

Appliances: Range, Dishwasher, Disposal, Microwave, 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
Door Features: Insulated Doors
Dwelling Type: Multi Family
Exterior: Frame
Fencing: Fenced/Enclosed, Fenced
Flooring: Wood, Tile, Vinyl
Lot Features: Level
Open Parking Y/N: Yes
Parcel Number: 897000
Parking Features: Paved Drive, Off Street
Parking Total: 3
Patio And Porch: Deck - Composite, Patio, Covered
Rent Includes: Unit 2(Heat, Water)
Road Responsibility: Public Maintained Road
Rooms Total: 11
Sewer: Public Sewer
Units: 2
Utilities: for Gas Range, for Electric Range
Water: Public
Window Features: Insulated Windows

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: Annalise Hardy
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 12:01:19 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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