George Cress of Real Broker Email: george@callcress.com Call/Text: 212-203-5251
11 Judges Hollow Road
Fairfield, CT 06824
$925,000Active$4,625 Buyer Rebate*
- 2
- beds
- 2
- baths
- 1,135
- SF
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.
Property Details
Listing Facts
- Acres
- 1.6
- Year built
- 1932
- Taxes (July 2026-June 2027)
- $7,972 (July 2026-June 2027)
- Price/SF
- $815
- Days on Market
- 162 Days
- MLS number
- 24176507
Highlights
- 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
School assignments as reported by SmartMLS.
Price History
| Date | Event | Price |
|---|---|---|
| Listed | $925,000 |
Listing Agent
William Pitt Sotheby's Int'l · (203) 227-1246
Lisa Hartmann · (203) 858-9126
Map
11 Judges Hollow Road, Fairfield, CT 06824
Nearby Properties for Sale
Homes for Sale in Fairfield ↗
Active$1,475,0004 beds · 2.5 ba · 2,360 sqft · Active50 Judges Hollow Road, Fairfield, CT 06824William Pitt Sotheby's Int'l
Active$2,695,0004 beds · 6 ba · 7,298 sqft · Active443 Brambley Hedge Circle, Fairfield, CT 06824William Pitt Sotheby's Int'l
Active$1,785,0005 beds · 5 ba · 6,136 sqft · Active203 Wildflower Lane, Fairfield, CT 06824Realty ONE Group Connect
Active$15,000,0007 beds · 8.5 ba · 9,129 sqft · Active4800 Congress Street, Fairfield, CT 06824William Pitt Sotheby's Int'l
Active$9,975,0007 beds · 8.5 ba · 9,129 sqft · Active4800 Congress Street, Fairfield, CT 06824William Pitt Sotheby's Int'lNearby sold homes
Sold Homes in Fairfield ↗
Sold 08/02/23$995,0004 beds · 2.5 ba · 2,360 sqft · Sold50 Judges Hollow Road, Fairfield, CT 06824William Pitt Sotheby's Int'l
Sold 07/20/22$1,443,8254 beds · 3.5 ba · 3,909 sqft · Sold275 Foggwood Road, Fairfield, CT 06824William Raveis Real Estate
Sold 10/22/26$1,500,0004 beds · 3.5 ba · 3,181 sqft · Sold1495 Westport Turnpike, Fairfield, CT 06824William Pitt Sotheby's Int'l
Sold 05/30/23$749,9004 beds · 2.5 ba · 2,320 sqft · Sold3250 North Street, Fairfield, CT 06824William Raveis Real Estate
Sold 10/12/23$1,510,0004 beds · 3.5 ba · 3,500 sqft · Sold53 Leslie Lane, Fairfield, CT 06824Coldwell Banker RealtyCould this be your next home?
Let’s talk about the property and what working with Cress could save you.
Save an estimated $4,625 with Cress*
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.
SmartMLS · Listing #24176507 · Active
Listing data checked: Oct 28, 2026, 7:40 PM EDT.
Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.
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