255 High St Hill RoadWindsor, MA 01270Price: $724,900

  • Price: $724,900
  • Est. Mortgage of $/month
  • 48 Days on Market
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Federal 30-year interest rate: 6.65% last updated on Aug 20, 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.
  • $724,900List Price
  • 5Bedrooms
  • 4Bathrooms
  • 3.24Acreage
  • 3,744Square Feet
Listed by Jesse Dimitropolis of RE/MAX COMPASS
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255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270
255 High St Hill Road Windsor MA 01270

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Tucked away on 3.24 private wooded acres, this one-of-a-kind Contemporary offers 3,744 sq. ft. of living space across three finished levels. Soaring ceilings, exposed timber beams, hardwood floors, and a dramatic center chimney create a warm yet impressive setting. The open floor plan is anchored by multiple wood-burning fireplaces, a pellet stove, and abundant natural light. Offering a total of five bedrooms and 3.5 baths, including a private in-law suite above the oversized attached two-car garage, this home provides exceptional flexibility for guests or extended living. Enjoy an owned 9.52 kW solar system, spacious decks, beautifully maintained grounds, and the privacy of a true Berkshire retreat just a short drive from everything the Berkshires and Northampton have to offer.

Property Details of 255 High St Hill Road

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Based on information submitted to BCMLS  as of August 23, 2026 . All data is obtained from various sources and has not been, and will not be, verified by broker or BCMLS.  All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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