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For sale
    • $749,900

    255 High Street Hill Rd, Windsor, MA 01270

    5beds
    3,744sqft
    : 
    $4,802/mo
    Get pre-qualified
    Single Family Residence
    Built in 1987
    3.24 Acres Lot
    $736,400 Zestimate®
    $200/sqft
    $-- HOA

    What's special

    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.
    28 days
    |
    868
    |
    32
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Jesse Dimitropolis 413-652-2802,

    RE/MAX COMPASS

    Source: BCMLS,MLS#: 250133MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: Second
      Bedroom
      • Description: In-Law Suite
      • Level: Second
      Bedroom 2
      • Level: Second
      Bedroom 3
      • Level: Second
      Bedroom 4
      • Description: In-Law Suite
      • Level: First
      Primary bathroom
      • Level: Second
      Half bathroom
      • Description: With Laundry
      • Level: First
      Full bathroom
      • Level: Second
      Full bathroom
      • Description: In-Law Suite
      • Level: First
      Dining room
      • Level: First
      Family room
      • Level: First
      Foyer
      • Level: First
      Great room
      • Level: Third
      Kitchen
      • Level: First
      Kitchen
      • Description: In-Law Suite
      • Level: First
      Living room
      • Level: First
      Living room
      • Description: In-Law Suite
      • Level: First
      Heating
      • Oil, Hot Water, Fireplace(s)
      Appliances
      • Included: Dryer, Range, Refrigerator, Washer
      Features
      • Interior Balcony, Radon Mitigation System
      • Flooring: Carpet, Ceramic Tile, Laminate, Wood
      • Windows: Skylight(s)
      • Basement: Radon Remed Sys,Garage Access,Full,Concrete
      • Has fireplace: Yes
      Interior area
      • Total structure area: 3,744
      • Total interior livable area: 3,744 sqft

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garaged & Off-Street
      • Attached garage spaces: 2
      • Details: Garaged & Off-Street
      Accessibility
      • Accessibility features: Accessible Bedroom, Accessible Full Bath
      Features
      • Patio & porch: Deck
      • Exterior features: Privacy, Landscaped
      • Has view: Yes
      • View description: Hill/Mountain
      Lot
      • Size: 3.24 Acres
      • Dimensions: 228x697
      Details
      • Parcel number: M 14 L 115
      • Zoning description: Residential

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Salt Box,Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Roof: Asphalt Shingles
      Condition
      • Year built: 1987

      Utilities & green energy

      • Electric: 200 Amp, Circuit Breakers
      • Sewer: Private Sewer
      • Water: Well
      • Utilities for property: Fiber Optic Availabl
      Green energy
      • Energy generation: Solar, Solar Panels Owned

      Community & HOA

      Location
      • Region: Windsor

      Financial & listing details

      • Price per square foot: $200/sqft
      • Tax assessed value: $464,100
      • Annual tax amount: $5,263
      • Date on market: 7/8/2026

        Estimated market value

        $736,400

        $700,000 - $773,000

        $3,339/mo

        Price history

        DateEventPrice
        7/8/2026Listed for sale$749,900+226%$200/sqft
        Source: BCMLS #250133 Report a problem
        10/15/1999Sold$230,000$61/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,263 +2.4%$464,100 +4.2%
        2024$5,138 +4.1%$445,200 +18.3%
        2023$4,935 -0.1%$376,400 +0.2%
        2022$4,940 +2.4%$375,700 +1.6%
        2021$4,826 +2.3%$369,800 +10.4%
        2020$4,718 +0%$335,100 -5.4%
        2019$4,717 -18.2%$354,400 -17.2%
        2018$5,764 +9.6%$428,200 +10.6%
        2017$5,258 +0.1%$387,200 -1.3%
        2016$5,254 -3.3%$392,400 -3.8%
        2015$5,432 +0.5%$408,100 -0.7%
        2014$5,406 +0.5%$410,800 -3.9%
        2013$5,381 +3.2%$427,400 -4.7%
        2012$5,214 -2.9%$448,700 +7.8%
        2011$5,368 +4.4%$416,100 -10%
        2010$5,141 -0.3%$462,300 -6.4%
        2009$5,156 +14.5%$493,900 +17.1%
        2008$4,504 -2.5%$421,700 +17.8%
        2007$4,618 +3.6%$358,000 +2.8%
        2006$4,456 +9.2%$348,100 +22.7%
        2005$4,081 +7.2%$283,800
        2004$3,806 +2.4%$283,800
        2003$3,718 +8.6%$283,800 +8.7%
        2002$3,424 $261,000
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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        Climate risks

        Neighborhood: 01270

        Getting around

        0 / 100
        Car-Dependent
        4 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Berkshire Trail
        • Middle: Nessacus Regional
        • High: Wahconah Regional

        Source: BCMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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