85 High Street, Winchester, MA 01890

$1,899,000 · For sale

85 High Street, Winchester

Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchester’s 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.

About this address

85 High Street is a 4-bedroom, 2.5-bath single-family home for sale in Winchester, MA 01890 with 3,757 square feet, asking $1,899,000. It was built in 1931. It has been on our site since October 30, 2026.

The median asking price among the 11 other 4-bedroom single-family homes for sale in Winchester is $1,699,000. This one asks about 12% more. At $505 a square foot, it compares with a median of $562 among the 42 other single-family homes for sale in Winchester with a stated size.

At 3,757 square feet, it is larger than 73% of the 11 other 4-bedroom single-family homes in Winchester with a stated size.

This home is assessed at $1,434,500 for fiscal year 2026. The assessor lists a lot of 0.29 acres.

It scores 12 out of 100 for walkability, from how close everyday places are.

The closest train or subway stop is Wedgemere (MBTA Lowell Line), about 1.1 miles away. The closest bus stop is Cambridge St @ Oneida Rd (MBTA route 350), about 0.5 miles away.

The closest public schools by level are Ambrose Elementary (0.3 miles), McCall Middle (1.4 miles) and Winchester High School (1.6 miles). The district decides which school serves an address.

Listing information from MLS Property Information Network (MLS PIN), MLS #73596915, deemed reliable but not guaranteed. Prices are compared with other homes listed on this site today. Trains and buses come from the transit agencies’ published schedules and schools from the National Center for Education Statistics. Distances are straight-line. Assessed values and past sales are public records from municipal assessors, published by MassGIS. An assessed value is set for taxation and may differ from market value.

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To ask about this home or book a tour, call Benjamin Realty at (617) 734-5050 or email [email protected].