23 Painter Hill Road
Roxbury, Connecticut 06783
Reduced from $1,095,000
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 1,782
- Acres
- 3.00
- Year Built
- 1990
- Neighborhood
- Painter Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!
Key Facts
- City/Town
- Roxbury
- Neighborhood
- Painter Hill
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1990
- Days on Market
- 83 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 1,782 sq ft
- Lot Size
- 3.00 acres
- Property Taxes
- $5,415 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
31
8 under contract
Median List Price
$1.29M
31 active listings
Median Closed Price
$1.40M
28 sales
Median Days on Market
89
31 active listings
Median $ / Sq Ft
$493
31 active listings
Sale-to-List Ratio
96.1%
28 sales
How this home compares
List Price
$1.05M
vs $1.29M median
19.0% below median
Price / Sq Ft
$589
vs $493 median
19.5% above median
Days on Market
83 days
vs 89 days median
6 days fresher than median
Based on 31 active and 28 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 29, 2026.
Location
23 Painter Hill Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,349
- Property Taxes$451
- Insurance$350
- 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
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1990
- New Construction
- No/Resale
- Living Area
- 1,782 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Appliances
- Cook TopOven/RangeRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullPartially Finished
Exterior & Lot
- Lot Size
- 3.00 acres
- Zoning
- A
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Wood
- Roof
- Asphalt Shingle
- Foundation
- Block
- Lot Description
- RollingOpen Lot
Listing & Financials
- Property Taxes
- $5,415 / Annually
- Days on Market
- 83
- MLS #
- 24167690
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 12:45 PM UTC.