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For sale
  • $925,000

    11 Judges Hollow Road, Fairfield, CT 06824

    2beds
    1,135sqft
    : Get pre-qualified
    Single Family Residence
    Built in 1932
    1.6 Acres Lot
    $903,300 Zestimate®
    $815/sqft
    $-- HOA

    What's special

    Mature treesPrivate driveHilltop propertySecluded pondRolling hillsHiking paths
    This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With trails leading directly from the back door to a secluded pond and hiking paths, it serves as an ideal weekend retreat and a convenient alternative to the Vermont or Connecticut River Valley. Located only 70 minutes from Grand Central via the Westport train station, this home offers easy access to both the Connecticut coastline and deep woods. This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With trails leading directly from the back door to a secluded pond and hiking paths, it serves as an ideal weekend retreat and a convenient alternative to the Vermont or Connecticut River Valley. Located only 70 minutes from Grand Central via the Westport train station, this home offers easy access to both the Connecticut coastline and deep woods.
    10 days
    |
    687
    |
    14
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Lisa Hartmann (203)858-9126,

    William Pitt Sotheby's Int'l 203-227-1246

    Source: Smart MLS,MLS#: 24176507MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 2
      • Bathrooms: 2
      • Full bathrooms: 2
      Primary bedroom
      • Level: Main
      Bedroom
      • Level: Main
      Heating
      • Wall Unit, Other
      Cooling
      • Wall Unit(s)
      Appliances
      • Included: None, Water Heater
      Features
      • Open Floorplan
      • Basement: Partial,Unfinished,Walk-Out Access
      • Attic: None
      • Has fireplace: No
      Interior area
      • Total structure area: 1,135
      • Total interior livable area: 1,135 sqft
      • Finished area above ground: 1,135

      Property

      Features
      • Patio & porch: Porch
      • Has private pool: Yes
      • Pool features: In Ground
      • Waterfront features: Beach Access
      Lot
      • Size: 1.6 Acres
      • Features: Wooded, Sloped
      Details
      • Additional structures: Shed(s)
      • Parcel number: 132905
      • Zoning: AAA

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch
      • Property subtype: Single Family Residence
      Materials
      • Shingle Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1932

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Golf, Public Rec Facilities
      • Subdivision: Greenfield Hill
      HOA
      • Has HOA: No
      Location
      • Region: Fairfield

      Financial & listing details

      • Price per square foot: $815/sqft
      • Tax assessed value: $233,660
      • Annual tax amount: $6,634
      • Date on market: 5/20/2026
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        Estimated market value

        $903,300

        $858,000 - $948,000

        $4,486/mo

        Price history

        DateEventPrice
        5/20/2026Listed for sale$925,000-2.6%$815/sqft
        Source: Smart MLS #24176507 Report a problem
        5/19/2026Listing removed$950,000$837/sqft
        Source: Smart MLS #24141884 Report a problem
        11/28/2025Listed for sale$950,000+35.9%$837/sqft
        Source: Smart MLS #24141884 Report a problem
        11/22/2009Listing removed$699,000$616/sqft
        Source: NCI #98391406 Report a problem
        11/8/2009Listed for sale$699,000+10.4%$616/sqft
        Source: NCI #98391406 Report a problem
        11/14/2005Sold$633,000$558/sqft
        Source: Smart MLS #98250841 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$6,634 +1.8%$233,660
        2024$6,519 +1.4%$233,660
        2023$6,428 +1%$233,660
        2022$6,365 +1%$233,660
        2021$6,304 +4.7%$233,660 +3.9%
        2020$6,023 $224,840
        2019$6,023 +1.6%$224,840
        2018$5,927 +2.1%$224,840
        2017$5,805 -1%$224,840 -4.9%
        2015$5,864 +1.6%$236,530
        2014$5,771 +2%$236,530
        2013$5,660 +6.5%$236,530
        2011$5,315 -18.4%$236,530 -30%
        2010$6,515 +2%$338,100
        2009$6,390 +1.7%$338,100
        2008$6,282 +6.7%$338,100
        2007$5,886 +4.4%$338,100
        2006$5,636 -9.7%$338,100 +34.3%
        2005$6,243 +6%$251,720
        2004$5,890 +8.8%$251,720
        2003$5,412 +21.2%$251,720 +64.7%
        2001$4,464 +85.3%$152,880
        2000$2,409 -41%$152,880
        1999$4,082 $152,880

        Find assessor info on the county website

        Monthly payment

        Est. payment

          Payment breakdown

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          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: 06824

          Getting around

          2 / 100
          Car-Dependent
          4 / 100
          Somewhat Bikeable

          Nearby schools

          GreatSchools rating
          Schools provided by the listing agent
          • Elementary: Burr
          • Middle: Tomlinson
          • High: Fairfield Warde

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

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