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4 Beds
3 Baths
3,757 sqft

$1,999,000

85 High St, Winchester MA, 01890

Price per sqft$532.07
Built in1931
Property size3,757 sqft
Property typeResidential

Overview

Active

Listed Aug 19, 2026

Updated 3 weeks ago

Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable 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.

$13,299/mo

Est. mortgage payment based on a $1,999,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
73565817

Interior Features

Bedrooms
4
Bathrooms
3
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.29 Acres

Other Property Details

Taxes
$15,671
Tax Frequency
Annually
Garage
Yes
55+/Senior Community
No

This listing is provided by Catherine Albiani with Better Homes and Gardens Real Estate - The Shanahan Group

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Data last updated 8:06 PM UTC, 9/3/2026

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