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257 High StreetWinchester, MA 01890Price: $3,299,000

  • Price: $3,299,000
  • Est. Mortgage of $/month
  • 63 Days on Market
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Federal 30-year interest rate: 6.17% last updated on Oct 30, 2025
* 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.
  • $3,299,000List Price
  • 5Bedrooms
  • 7Bathrooms
  • 1.68Acreage
  • 1994Year Built
  • 7,101Square Feet
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Spectacular Winchester estate offering over 7000 sf of living space with exceptional privacy and exclusivity on an oversized lot. This grand home spans over three full levels with extraordinary living spaces highlighted by a soaring two-story family room, elegant mahogany library w/ fplc, custom built-ins. The large country kitchen offers commercial grade appliances, w access to glorious deck, mudroom, pantry & oversized 2 car garage. The 2nd floor offers a stunning master w sitting area, marble bath & walk in closet. 3 add'l BR's, all generously sized. The expansive lower level features an inviting screened "Florida room" family space that opens to a bluestone patio with fire pit, overlooking expansive meticulously maintained lawn & an outdoor shower! Additionally in the LL, there is a movie theatre, full kitchen, gym, bedroom, game room w fplc, perfect for ADU/ extended family or for everyday living and entertaining. Must see this fabulous home~ The ultimate home for hosting!

Property Details of 257 High Street

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Listed by Kim Covino & Co. Team of Compass