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85 High Street, Winchester, MA 01890

$1,749,000
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New to the Market Active Price Reduced $150,000 on November 5th, 2026
BEDS4 BATHS2 full 1 partial SQUARE FEET3,757 MLS#73596915
STATUSActive PROPERTY TYPEResidential - Single Family

Property Description

Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchesters most desirable neighborhoods, offering timeless architecture, exceptional flexibility, within a rare setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location??ready to be loved from day one.

85 High Street | MLS# 73596915

This single family home located at 85 High Street, Winchester, MA 01890 is currently listed for sale with an asking price of $1,749,000. This property was built in 1931 and has 4 bedrooms and 2 full and 1 partial baths with 3757 sq. ft. Search Winchester real estate on www.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Bulkhead, Sump Pump, Concrete
Cooling: Central Air
Fenced: Yes
Fireplaces: 1
Garage: 2
Heating: Steam, Natural Gas
Home Style: Colonial
Lot Size: 0.29 Acres
Roof Type: Shingle
Taxes: $15,671
Year Built: 1931

Amenities

Dining Area
Breakfast Bar / Nook
Foyer
Bonus Room
Patio
Rain Gutters
Professional Landscaping
Sprinkler System
Screens
Fenced Yard

Feature Descriptions

Appliances: Water Heater, Oven, Dishwasher, Disposal, Range, Refrigerator, Washer, Dryer
Building Area Total: 3757
Community Features: Public Transportation, Tennis Court(s), Park, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station
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: 6
Dining Room: Flooring - Hardwood
Electric: Circuit Breakers,200+ Amp Service, Other (See Remarks)
Family Room: Closet/Cabinets - Custom Built, Flooring - Wood
Fencing: Fenced/Enclosed, Fenced
Fireplace Features: Living Room
Fireplace Y/N: Yes
Flooring: Tile, Hardwood, Flooring - Hardwood, Laminate
GarageY/N: Yes
HeatingY/N: 1
Kitchen: Flooring - Hardwood, Countertops - Stone/Granite/Solid, Recessed Lighting
Laundry: Second Floor, Electric Dryer Hookup, Washer Hookup
Living Room: Closet/Cabinets - Custom Built, Flooring - Hardwood
Lot Features: Corner Lot, Level
Master Bathroom: Yes
Master Bedroom: Bathroom - Full, Walk-In Closet(s), Flooring - Wall to Wall Carpet
Open Parking Y/N: Yes
Parcel Number: M:021 B:0086 L:0,900221
Parking Features: Detached, Garage Door Opener, Heated Garage, Storage, Off Street, Paved
Parking Total: 6
Patio And Porch: Patio
Road Responsibility: Public Maintained Road
Rooms Total: 12
Sewer: Public Sewer
Utilities: for Electric Range, for Electric Dryer, Washer Hookup
Water: Public
Window Features: Screens

Room Sizes

Bathroom 1: 8.00 X 6.00 Level - First
Bathroom 2: 8.00 X 6.00 Level - Second
Bathroom 3: 13.00 X 7.00 Level - Second
Bedroom 2: 15.00 X 9.00 Level - Second
Bedroom 3: 14.00 X 12.00 Level - Second
Bedroom 4: 14.00 X 10.00 Level - Second
Bedroom 5: 19.00 X 13.00 Level - Third
Dining Room: 13.00 X 14.00 Level - First
Family Room: 17.00 X 16.00 Level - First
Kitchen: 11.00 X 11.00 Level - First
Living Room: 24.00 X 14.00 Level - First
Primary Bedroom: 23.00 X 12.00 Level - Second

Local Schools

High School: Whs
Middle School: Mccall
Elementary School: Ambrose

Listed By / Shown By

Listed By

Agency Name: Better Homes and Gardens Real Estate - The Shanahan Group
Agent Name: Catherine Albiani
Agency Phone: 781-729-9030

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Estimated Payment

$ 5,708.56 per month $3,892.52 Principal & Interest $1,305.92 Property Tax $510.13 Homeowner's Insurance

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