220 Painter Hill Road
Roxbury, Connecticut 06783
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 4,570
- Acres
- 4.68
- Year Built
- 2007
- Neighborhood
- Painter Hill
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- Painter Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 2007
- Days on Market
- 102 days
- Beds
- 4
- Baths
- 4 full · 1 half
- Living Area
- 4,570 sq ft
- Lot Size
- 4.68 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $10,164 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
30
8 under contract
Median List Price
$1.30M
30 active listings
Median Closed Price
$1.40M
29 sales
Median Days on Market
87
30 active listings
Median $ / Sq Ft
$506
30 active listings
Sale-to-List Ratio
96.1%
29 sales
How this home compares
List Price
$2.90M
vs $1.30M median
2.2× the median
Price / Sq Ft
$633
vs $506 median
25.1% above median
Days on Market
102 days
vs 87 days median
15 days longer than median
Based on 30 active and 29 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 27, 2026.
Location
220 Painter Hill Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$14,761
- Property Taxes$847
- Insurance$965
- 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
- Colonial
- Year Built
- 2007
- New Construction
- No/Resale
- Living Area
- 4,570 sq ft
- Below Grade
- 700 sq ft
Schools
- Elementary
- Booth Free
- Middle
- Regional District 12
- High
- Regional District 12
Interior
- Heating
- Heat PumpHot AirZoned
- Heat Fuel
- ElectricOilPropane
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Laundry Location
- Main level
- Appliances
- Gas RangeMicrowaveRange HoodSubzeroDishwasherWasherDryerWine Chiller
- Basement
- FullPartially Finished
- In-Law Apartment
- Possible
- Interior Features
- Auto Garage Door OpenerElevatorOpen Floor PlanSecurity System
- Additional Rooms
- FoyerLaundry RoomMud RoomSitting RoomWine Cellar
- Accessibility
- Hallways 36+ Inches Wide
Exterior & Lot
- Lot Size
- 4.68 acres
- Zoning
- C
- Garage / Parking
- 3 garage spacesCarportAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedSalt WaterLap PoolIn Ground Pool
- Construction
- ClapboardHardie Board
- Color
- White
- Roof
- Asphalt ShingleMetal
- Foundation
- Concrete
- Exterior Features
- Porch-ScreenedUnderground UtilitiesPorchDeckGarden AreaStone WallFrench DoorsUnderground SprinklerPatio
- Lot Description
- Fence - StoneLightly WoodedClearedProfessionally LandscapedOpen Lot
Listing & Financials
- Property Taxes
- $10,164 / Annually
- Days on Market
- 102
- MLS #
- 24167130
- MLS Status
- Active
Similar Properties
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Co-Listed By
Pels Matthews
W. Raveis Lifestyles Realty
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 8:20 PM UTC.