For sale

$925,000

11 Judges Hollow Road, Fairfield, CT 06824

2beds

1,135sqft

$5,991/mo

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Single Family Residence

Built in 1932

1.6 Acres Lot

$888,000 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.

88 days

581

11

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: $415,450
Annual tax amount: $7,972
Date on market: 5/20/2026

Estimated market value

$888,000

$844,000 - $932,000

$4,272/mo

Price history

Date	Event	Price
5/20/2026	Listed for sale	$925,000-2.6%$815/sqft
Source: Smart MLS #24176507 Report a problem
5/19/2026	Listing removed	$950,000$837/sqft
Source: Smart MLS #24141884 Report a problem
11/28/2025	Listed for sale	$950,000+35.9%$837/sqft
Source: Smart MLS #24141884 Report a problem
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: Smart MLS #98250841 Report a problem

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