Great value, excellent location! Painter Hill is one of Roxbury's most scenic country roads. Close to Toplands Farm with beautiful pastoral views, a short drive to Maple Bank Farm for local produce, and just steps to a quiet dirt road for long walks. This charming Cape, built by the reputable local builder/owner in 2005, has 3 BR, 2.5 baths, a free-form Gunite pool and amazing outdoor living spaces. A covered front porch opens to the public living spaces. The main floor features a light-filled Great Room with a shiplap cathedral ceiling. The bookcases, bar and gas fireplace mantle are crafted from antique chestnut, and French doors open to a deck and patio. The dining room has a wood burning fireplace. An eat-in kitchen has a center island, granite counters, double ovens, refrigerator/freezer and a 4 burner gas cooktop. The primary bedroom suite is on the main level featuring built-in cabinets, a full bath and walk-in closet. There are two guest bedrooms and one full bath on the second floor. The lower level has one finished room and washer dryer. There is ample basement storage and access to a spacious two-car garage.
Sold for $1,195,000 on 11/07/25
$1,195,000
158 Painter Hill Road, Roxbury, CT 06783
3beds
2,793sqft
Single Family Residence
Built in 2005
3.91 Acres Lot
$1,202,600 Zestimate®
$428/sqft
$5,023 Estimated rent
Home value
$1,202,600
$974,000 - $1.48M
$5,023/mo
Zestimate® history
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What's special
Zillow last checked: 8 hours ago
Listing updated: November 07, 2025 at 02:24pm
Listed by:
Bonnie Garguilo (860)921-7648,
William Pitt Sotheby's Int'l 860-868-6600
Bought with:
Carla P. Mascaro, RES.0826631
William Pitt Sotheby's Int'l
Source: Smart MLS,MLS#: 24120750
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Bedroom Suite, Built-in Features, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Main
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Dining room
- Features: Fireplace, Hardwood Floor
- Level: Main
Great room
- Level: Main
Kitchen
- Features: Dining Area, Kitchen Island, Hardwood Floor
- Level: Main
Other
- Level: Lower
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Gas Cooktop, Oven, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Lower Level
Features
- Basement: Full,Storage Space,Garage Access,Interior Entry,Partially Finished
- Attic: None
- Number of fireplaces: 1
Interior area
- Total structure area: 2,793
- Total interior livable area: 2,793 sqft
- Finished area above ground: 2,583
- Finished area below ground: 210
Property
Parking
- Total spaces: 2
- Parking features: Attached
- Attached garage spaces: 2
Features
- Patio & porch: Porch, Deck, Patio
- Exterior features: Stone Wall
- Has private pool: Yes
- Pool features: Gunite, In Ground
Lot
- Size: 3.91 Acres
- Features: Few Trees, Sloped
Details
- Parcel number: 867350
- Zoning: C
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Cape Cod
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Asphalt,Gable
Condition
- New construction: No
- Year built: 2005
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & neighborhood
Location
- Region: Roxbury
- Subdivision: Painter Hill
Price history
| Date | Event | Price |
|---|---|---|
| 11/7/2025 | Sold | $1,195,000$428/sqft |
Source:  Smart MLS #24120750 | ||
| 10/8/2025 | Pending sale | $1,195,000$428/sqft |
Source: Smart MLS #24120750 | ||
| 8/29/2025 | Listed for sale | $1,195,000+1227.8%$428/sqft |
Source: Smart MLS #24120750 | ||
| 2/26/2002 | Sold | $90,000$32/sqft |
Source: Public Record | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,295 +3.2% | $561,190 |
| 2024 | $7,071 | $561,190 |
| 2023 | $7,071 -2.6% | $561,190 +17.9% |
Find assessor info on the county website
Neighborhood: 06783
Nearby schools
GreatSchools rating
- NABooth Free SchoolGrades: K-5Distance: 1.8 mi
- 8/10Shepaug Valley SchoolGrades: 6-12Distance: 1.5 mi
Schools provided by the listing agent
- Elementary: Booth Free
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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$1,202,600
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$1,226,652