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133 Painter Hill Road

Woodbury, Connecticut 06798

ACTIVE$395,000
Beds
0
Baths
0
SqFt
Acres
2.53
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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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

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

Property + 4 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$2,267

per 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.

Listed By

Judith Auchincloss

(203) 770-3300

Klemm Real Estate Inc

(860) 868-7313

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.