Tashna Bowes

11 Judges Hollow Road

Fairfield, CT
$ 925,000 Beds 2 Baths 2 Sq 1,135
Monthly Estimate* How much can I afford?

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.

Single Family

  • Price
  • $ 925,000
  • City
  • Fairfield
  • Bedrooms
  • 2
  • Full Bathrooms
  • 2
  • County
  • Fairfield
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 1.6 Acres
  • Zip
  • 06824
  • Sqr Footage
  • 1,135
  • Year Built
  • 1932
  • Taxes
  • $ 7972
  • Style
  • MLS#
  • 24176507
Listed By: Lisa Hartmann 203-858-9126 with William Pitt Sotheby's Int'l. - (203) 227-1246
Data Source: Smart MLS

Features

General

Zoning AAA
Neighborhood Greenfield Hill
County Fairfield
Tax Year July 2026-June 2027
Property Type Single Family For Sale
Status Active
Acres 1.6
Directions Rt 136 To Judges Hollow Rd- Travel South On Narrow Lane.
High School Fairfield Warde
City Fairfield
Elementary School Burr
Sq Ft Total 1135
DOM 83
Year Built 1932
Style Ranch
Year Built Source Public Records
Pool Description In Ground Pool

Interior Features

Cooling System Wall Unit
Total Rooms 4
Basement Description Partial,Unfinished,Walk-out

Exterior Features

Water Source Private Well
Lot Description Treed,Sloping Lot
Color White

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Burr Elementary School
Middle School Unknown Middle School
High School Fairfield Warde High School

Price History

5/20/2026 Listed $925,000

Property vs Zip Code Average in 06824

Price
AVG $2.56M
$930K
Year Built
AVG 1967
1932

In The Neighborhood

Areas That We Cover

11 Judges Hollow Road Fairfield, CT is a Single Family Home for sale at $925000 with 1135 sqft and a lot size of 1.6 Acres Acre(s). 11 Judges Hollow Road Fairfield has 2 bedrooms, 2 baths and was built in 1932. The property's zip code is 06824 which is in Fairfield, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.

Tashna Bowes

Tashna Bowes

347-698-0908

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