296 Painter Hill Rd, Roxbury, CT 06783
OFF MARKET

296 Painter Hill Rd
Roxbury, CT 06783

  • 5 Beds
  • 3.5 Baths
  • 3,364 sqft (on 4 acres)

$1,600,100

Trulia Estimate
as of Jun 23, 2026

$1,600,100

Trulia Estimate
as of Jun 23, 2026
5 Beds
3.5 Baths
3,364 sqft
(on 4 acres)

Local Information

  • Map ViewExplore the area around 296 Painter Hill Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

One of Roxbury's finest addresses abutting the Alexander Calder estate. This modern farmhouse is a real stunner with an open floor plan, high ceilings and light filled interiors. Its sits high a top Painter Hill and has views across protected land. 5 bedrooms 3.5 baths. Gourmet kitchen with bar stool seating and walk-in pantry. Master suite with spa-like bath room. Spin cycle studio, playroom, media room/office. The tree lined driveway shines with pink blossoms in the Spring. Large barn. Super chic 3 car garage with glass doors.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 296 Painter Hill Rd

Interior Features

Interior Details
BasementNumber of Rooms: 12
Heating & Cooling
Heating: Other, OilAir ConditioningCooling System: CentralHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
DishwasherDryerWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: MetalExterior: Wood
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1978Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 2

Lot Information

Lot Area: 4.00 acres

Price History for 296 Painter Hill Rd

DatePriceEventSource
01/16/2020$882,500Sold
Smart MLS #170052871
11/26/2019$950,000PriceChange
Agent Provided
09/10/2019$1,050,000PriceChange
Agent Provided
04/29/2019$1,150,000PriceChange
Agent Provided
01/22/2019$1,295,000PriceChange
Agent Provided
01/07/2019$1,350,000PriceChange
Agent Provided
07/07/2018$1,495,000PriceChange
Agent Provided
02/15/2018$1,550,000Listed For SaleAgent Provided
02/15/2018$5,500ListingRemovedAgent Provided
06/06/2017$5,500Listed For RentAgent Provided
10/15/2010$60,000ListingRemovedAgent Provided
10/01/2010$60,000Listed For SaleAgent Provided
04/30/2010$1,200,000Sold
Smart MLS #L127207
11/17/2008$2,100,000ListingRemovedAgent Provided
07/27/2008$2,100,000Listed For SaleAgent Provided
03/14/2005$680,000Sold
Smart MLS #W1018561

Market trends in Roxbury

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
34
11MoM
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Property Tax and Assessment

Year2025
Tax$11,228
Assessment$863,730
Home facts updated by county records

Comparable Sales for 296 Painter Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
277 Painter Hill Road, Roxbury, CT
0.18
Single-Family Home
$2,547,500
01/30/26
3
2.5
2,559
247 Painter Hill Rd, Roxbury, CT
0.47
Single-Family Home
$1,375,000
03/27/26
4
4
2,396
76 Cross Brook Rd, Roxbury, CT
0.31
Single-Family Home
$850,000
03/11/26
3
2
1,371
187 Painter Hill Rd, Roxbury, CT
0.88
Single-Family Home
$1,133,000
08/21/25
4
3.5
3,155
253 Tophet Road, Roxbury, CT
0.70
Single-Family Home
$1,500,000
11/18/25
4
3.5
2,437
158 Painter Hill Road, Roxbury, CT
0.91
Single-Family Home
$1,195,000
11/07/25
3
2.5
2,793
7 Jonathan Dr, Roxbury, CT
1.25
Single-Family Home
$1,050,000
12/09/25
3
3
1,976
143 Tophet Road, Roxbury, CT
1.18
Single-Family Home
$1,925,000
02/17/26
4
5.5
5,848
364 Hoop Pole Hill Road, Woodbury, CT
1.65
Single-Family Home
$975,000
10/01/25
5
3
3,450
123 Cross Brook Road, Woodbury, CT
0.89
Single-Family Home
$590,000
06/17/26
1
2
1,564

Nearby homes

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Assigned Schools

These are the assigned schools for 296 Painter Hill Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Roxbury

At least 2 Trulia users voted on each feature.

  • 100 % Say there's holiday spirit

  • 100 % Say car is needed

  • 100 % Say it's quiet

  • 80 % Say yards are well-kept

  • 80 % Say it's dog friendly

  • 80 % Say parking is easy

  • 67 % Say there's wildlife

  • 50 % Say people would walk alone at night

  • 50 % Say they plan to stay for at least 5 years

  • 29 % Say neighbors are friendly

  • 25 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Lisa r. h.
    "This is an incredibly supportive town, with many young families. Lots of townwide events to meet new people, and friendly neighbors. We moved in 9 years ago and love living here!"
    2
    Flag
  • Maria T.
    "Peaceful and surrounded by nature. The perfect escape from the city or a great place to live full time."
    0
    Flag
  • Katherine
    "This is one of the most gorgeous towns in Connecticut. Quintessential New England, with lots of privacy - yes there are celebs - but who cares! They are just people too. You get the best of everything - lovely town green, no traffic, a short drive to everything you need, acreage with your house and low taxes. People are friendly, helpful, nice to you and no smog!!!!!!!!! Yes, we love it here. "
    0
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Homes for sale near 296 Painter Hill Rd

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Off Market Homes Near 296 Painter Hill Rd

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296 Painter Hill Rd, Roxbury, CT 06783 is a 5 bedroom, 4 bathroom, 3,364 sqft single-family home built in 1978. This property is not currently available for sale. 296 Painter Hill Rd was last sold on Jan 16, 2020 for $882,500. The current Trulia Estimate for 296 Painter Hill Rd is $1,600,100.