133 Painter Hill Road
Woodbury, Connecticut 06798
- Beds
- 0
- Baths
- 0
- SqFt
- —
- Acres
- 2.53
- Property Type
- Land

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Nestled along one of Woodbury's finest country roads, this exceptional 2.53-acre parcel offers a rare masterclass in privacy and natural beauty. Located just moments from the Roxbury town line, the gently rolling landscape is framed by mature trees and directly abuts the Arthur Miller Preserve and the Frank and Ellen McCort protected Land Trust. Positioned just two homes away from the historic Calder Estate, the setting creates an extraordinary sense of quietude and absolute seclusion. The property features a magnificent all-season running stream with its own natural waterfall, dramatically enhancing the native wildlife and scenic beauty of the area. Enveloped by the timeless allure of Litchfield County, this land offers an ideal canvas for an architectural masterpiece, a private weekend retreat, or a magnificent legacy estate. Its pristine setting, open spaces, and dramatic yet intimate feel provide the perfect balance of country elegance and everyday livability. Peerless privacy, a coveted location, protected surroundings, and an immediate neighborhood of significant homes make this a compelling opportunity in one of Connecticut's most desirable country settings-just minutes from the refined charm of Roxbury and Washington, and approximately 90 minutes from NYC.
Key Facts
- City/Town
- Woodbury
- Neighborhood
- N/A
- Property Type
- Land
- Days on Market
- 27 days
- Beds
- 0
- Baths
- 0 baths
- Lot Size
- 2.53 acres
- Property Taxes
- $1,457 / Annually
Market Snapshot
The Woodbury Market
Land · trailing 12 months
Active Listings
4
3 under contract
Median List Price
$697,500
4 active listings
Median Closed Price
$127,500
6 sales
Median Days on Market
18
4 active listings
Median $ / Sq Ft
--
4 active listings
Sale-to-List Ratio
89.6%
6 sales
How this home compares
List Price
$395,000
vs $697,500 median
43.4% below median
Price / Sq Ft
--
Median unavailable
Limited comparable data
Days on Market
27 days
vs 18 days median
9 days longer than median
Based on 4 active and 6 closed sales (trailing 12 mo) of land in Woodbury. Source: SmartMLS · As of July 28, 2026.
Location
133 Painter Hill Road, Woodbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,014
- Property Taxes$121
- Insurance$132
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Woodbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Land
- Subtype
- SingleFamilyResidence
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Exterior & Lot
- Lot Size
- 2.53 acres
- Zoning
- OS100
- Waterfront Details
- Not Applicable
- Water Source
- Well Required
- Sewer
- Septic Required
- Lot Description
- Some WetlandsSloping LotOpen Lot
Listing & Financials
- Property Taxes
- $1,457 / Annually
- Days on Market
- 27
- MLS #
- 24187054
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Jamie Marcoux
Klemm Real Estate Inc
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 7:01 AM UTC.