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85 High StreetWinchester, MA 01890Price: $1,999,000

  • Price: $1,999,000
  • Est. Mortgage of $/month
  • 12 Days on Market
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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Aug 27, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $1,999,000List Price
  • 4Bedrooms
  • 3Bathrooms
  • 3,757Square Feet
  • 0.29Acreage

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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.

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Listed by Catherine Albiani of Better Homes and Gardens Real Estate - The Shanahan Group

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