20 Painter Hill Road
Roxbury, Connecticut 0683
- Beds
- 0
- Baths
- 0
- SqFt
- —
- Acres
- 57.19
- Neighborhood
- Painter Hill
- 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
A masterclass in privacy and scale. A newly constructed stone-lined & gated driveway ascends through 57+ acres of pristine Litchfield County landscape to a magnificent hilltop sanctuary. This estate-quality offering, spanning two separate parcels, is defined by its dramatic sweeping views and an extraordinary sense of quietude. Enveloped by the protected forests of the Roxbury Land Trust, the terrain is a symphony of nature: a shimmering pond, a meandering stream, and ancient mature trees. This is a rare opportunity to cultivate a legacy estate just moments from the refined charm of Roxbury and Washington, and a mere 90 minutes from Manhattan. Improvements Include: 3 wells; irrigation system; driveway & underground power. The ultimate canvas for a life well-lived.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- Painter Hill
- Property Type
- Land
- Days on Market
- 66 days
- Beds
- 0
- Baths
- 0 baths
- Lot Size
- 57.19 acres
- Property Taxes
- $13,828 / Annually
Market Snapshot
The Roxbury Market
Land · trailing 12 months
Active Listings
9
2 under contract
Median List Price
$490,000
9 active listings
Median Closed Price
$453,250
4 sales
Median Days on Market
96
9 active listings
Median $ / Sq Ft
--
9 active listings
Sale-to-List Ratio
88.0%
4 sales
How this home compares
List Price
$4.00M
vs $490,000 median
8.2× the median
Price / Sq Ft
--
Median unavailable
Limited comparable data
Days on Market
66 days
vs 96 days median
30 days fresher than median
Based on 9 active and 4 closed sales (trailing 12 mo) of land in Roxbury. Source: SmartMLS · As of July 27, 2026.
Location
20 Painter Hill Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$20,369
- Property Taxes$1,152
- Insurance$1,332
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Roxbury
- Neighborhood
- Painter Hill
- County
- Litchfield
- Subdivision
- no
Residence
- Property Type
- Land
- Subtype
- SingleFamilyResidence
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Exterior & Lot
- Lot Size
- 57.19 acres
- Zoning
- A&C
- Waterfront
- Direct waterfront
- Waterfront Details
- Pond
- Water Source
- Well Required
- Sewer
- Septic Required
- Flood Zone
- No
- Lot Description
- SecludedLightly WoodedClearedRollingOpen Lot
Listing & Financials
- Property Taxes
- $13,828 / Annually
- Days on Market
- 66
- MLS #
- 24176550
- MLS Status
- Under Contract - Continue to Show
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Graham Klemm
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 7/27/2026. 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 7/27/2026 at 7:25 AM UTC.