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.
For sale
$925,000
11 Judges Hollow Road, Fairfield, CT 06824
2beds
1,135sqft
Est.: 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
- 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#: 24176507
Tour with a local agent
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
Estimated market value
$903,300
$858,000 - $948,000
$4,486/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/20/2026 | Listed for sale | $925,000-2.6%$815/sqft |
Source: | ||
| 5/19/2026 | Listing removed | $950,000$837/sqft |
Source: | ||
| 11/28/2025 | Listed for sale | $950,000+35.9%$837/sqft |
Source: | ||
| 11/22/2009 | Listing removed | $699,000$616/sqft |
Source: NCI #98391406 Report a problem | ||
| 11/8/2009 | Listed for sale | $699,000+10.4%$616/sqft |
Source: NCI #98391406 Report a problem | ||
| 11/14/2005 | Sold | $633,000$558/sqft |
Source: | ||
Public tax history
| Year | Property taxes | Tax 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 | $152,880 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
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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
Nearby schools
GreatSchools rating
- 8/10Burr Elementary SchoolGrades: K-5Distance: 2.2 mi
- 8/10Tomlinson Middle SchoolGrades: 6-8Distance: 5.7 mi
- 9/10Fairfield Warde High SchoolGrades: 9-12Distance: 5 mi
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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A local lender can help you make sure your offer is ready when you are.
- Connecticut
- Fairfield County
- Fairfield
- 06824
- 11 Judges Hollow Road








