11 Judges Hollow Road
Fairfield, Connecticut 06824
- Beds
- 2
- Baths
- 2
- SqFt
- 1,135
- Acres
- 1.60
- Year Built
- 1932
- Neighborhood
- Greenfield Hill
- Property Type
- Single Family
Matt Caiola
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About This Home
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.
Key Facts
- City/Town
- Fairfield
- Neighborhood
- Greenfield Hill
- Property / Style
- Single Family · Ranch
- Year Built
- 1932
- Days on Market
- 68 days
- Beds
- 2
- Baths
- 2 full
- Living Area
- 1,135 sq ft
- Lot Size
- 1.60 acres
- Property Taxes
- $6,634 / Annually
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
89
105 under contract
Median List Price
$1.57M
89 active listings
Median Closed Price
$1.16M
571 sales
Median Days on Market
33
89 active listings
Median $ / Sq Ft
$500
89 active listings
Sale-to-List Ratio
101.9%
571 sales
How this home compares
List Price
$925,000
vs $1.57M median
41.3% below median
Price / Sq Ft
$815
vs $500 median
63.0% above median
Days on Market
68 days
vs 33 days median
35 days longer than median
Based on 89 active and 571 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of July 28, 2026.
Location
11 Judges Hollow Road, Fairfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,716
- Property Taxes$553
- Insurance$308
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Fairfield
- Neighborhood
- Greenfield Hill
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1932
- New Construction
- No/Resale
- Living Area
- 1,135 sq ft
Schools
- Elementary
- Burr
- High
- Fairfield Warde
Interior
- Heating
- Wall UnitOther
- Cooling
- Wall Unit
- Appliances
- None
- Basement
- PartialUnfinishedWalk-out
- Interior Features
- Open Floor Plan
Exterior & Lot
- Lot Size
- 1.60 acres
- Zoning
- AAA
- Waterfront Details
- Beach Rights
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- In Ground Pool
- Construction
- Shingle
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- ShedPorch
- Lot Description
- TreedSloping Lot
Listing & Financials
- Property Taxes
- $6,634 / Annually
- Days on Market
- 68
- MLS #
- 24176507
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 5:20 AM UTC.