Fairfield, CT / 122 DAYS ON MARKET

11 Judges Hollow RoadFairfield, CT 06824

Asking price$925,000Active

Our Take

11 Judges Hollow Road in Fairfield is a 1930s rustic hunting cabin on 1.6 wooded acres at the end of a private drive. The hilltop setting includes mature trees, rolling hills, and 18th-century stone walls, with the property surrounded by the 186-acre Brett Woods Conservation Area. Trails lead from the back door to a secluded pond and hiking paths. Main Street Westport is eight minutes away, and Grand Central is 70 minutes via the Westport train station.

11 Judges Hollow Road — photo 1
1 / 10

Estimated buyer rebate

Buy with Cress and Save $4,625 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 20% rebate. Actual savings depend on final purchase price and commission received.

(212) 203-5251 george@cress.coContact form →

At a glance

Active · MLS #24176507
Bedrooms
2
BathroomsBaths
2 full / 0 half
Square feet
1,135
Year built
1932
Acres
1.6
Property taxes
$7,972

July 2026-June 2027

What stands out

  • 1930s rustic hunting cabin
  • 1.6 wooded acres at a private-drive end
  • Hilltop setting with mature trees and rolling hills
  • 18th-century stone walls
  • Surrounded by 186-acre Brett Woods Conservation Area
  • Trails from the back door to a secluded pond
  • Eight minutes from Main Street Westport
  • 70 minutes from Grand Central via Westport train station
Read the full listing description

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.

Schools

Elementary
Burr
Middle
Tomlinson
High
Fairfield Warde

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

Open Google Maps ↗

11 Judges Hollow Road, Fairfield, CT 06824

Price history

DateEventPrice
Originally listed$925,000

Intermediate price changes and previous listings may not be included.

Could this be your next home?

Let’s talk about the property—and what working with Cress could save you.

Inquire about this property →

*Estimate: $925,000 asking price × assumed 2.5% buyer-agent commission × 20% rebate = $4,625. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by William Pitt Sotheby's Int'l · (203) 227-1246

Lisa Hartmann

SmartMLS · Listing #24176507 · Active

Listing data checked: Sep 18, 2026, 7:05 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

For personal, noncommercial use to identify properties you may be interested in purchasing.