297 Painter Hill Road
Roxbury, Connecticut 06783
- Beds
- 4
- Baths
- 5 | 2
- SqFt
- 6,139
- Acres
- 14.81
- Year Built
- 1989
- Neighborhood
- Painter Hill
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. 3rd floor loft. Recreation Room/Guest Apartment over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, additional bedroom, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- Painter Hill
- Property / Style
- Single Family · Other
- Year Built
- 1989
- Days on Market
- 8 days
- Beds
- 4
- Baths
- 5 full · 2 half
- Living Area
- 6,139 sq ft
- Lot Size
- 14.81 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $42,515 / 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
88
30 active listings
Median $ / Sq Ft
$506
30 active listings
Sale-to-List Ratio
96.1%
29 sales
How this home compares
List Price
$4.50M
vs $1.30M median
3.5× the median
Price / Sq Ft
$732
vs $506 median
44.7% above median
Days on Market
8 days
vs 88 days median
80 days fresher than median
Based on 30 active and 29 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 28, 2026.
Location
297 Painter Hill Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$22,919
- Property Taxes$3,543
- Insurance$1,498
- 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
- Other
- Year Built
- 1989
- New Construction
- No/Resale
- Living Area
- 6,139 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Laundry Location
- 1 Laundry Room Main1 Basement
- Appliances
- Gas CooktopWall OvenMicrowaveRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullInterior AccessPartially FinishedFull With Walk-Out
- Additional Rooms
- FoyerGymLaundry RoomWine Cellar
Exterior & Lot
- Lot Size
- 14.81 acres
- Zoning
- C
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- Brook
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- ShingleCedarRedwood
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- SecludedLightly WoodedSloping LotClearedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $42,515 / Annually
- Days on Market
- 8
- MLS #
- 24192621
- 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 7/28/2026. 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.