357 Painter Hill Rd, Roxbury, CT 06783
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Property image
OFF MARKET

357 Painter Hill Rd
Roxbury, CT 06783

  • 3 Beds
  • 3 Baths
  • 2,156 sqft (on 12.36 acres)

$2,013,400

Trulia Estimate
as of Jul 21, 2026
Est. Refi. Payment $13,285/mo*
Refinance Your Home

$2,013,400

Trulia Estimate
as of Jul 21, 2026
Est. Refi. Payment $13,285/mo*
Refinance Your Home
3 Beds
3 Baths
2,156 sqft
(on 12.36 acres)

Local Information

  • Map ViewExplore the area around 357 Painter Hill Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Description

"Painter Hill Farm" - 3 Br, 1765 Colonial On 23 Acres With A 1 Br Guesthouse, View, Tennis Court, Gunite Pool. Tenant Pays Security Deposit, Outsidemaintenace, Utilities. Term: October 1, 2016 - April 30, 2017. Asking $5,000/month.
357 Painter Hill Rd, Roxbury, CT 06783 is a 3 bedroom, 3 bathroom, 2,156 sqft single-family home built in 1800. It last sold for $1,600,000 on Jan 25, 2019. More recently, it was listed as a rental in June 2017 with an asking price of $5,000 per month. That rental listing was removed on November 2, 2017. It is currently off market. The Trulia Estimate is $2,013,400, with a rent estimate of $4,829/month.

Home Details for 357 Painter Hill Rd

Property Information

Year Built
Year Built: 1800
Property Type / Style
Property Type: Single Family Home

Interior Features

Interior Details
Number of Rooms: 9
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Community

Units in Building: 5

Lot Information

Lot Area: 12.36 acres

Price History for 357 Painter Hill Rd

DatePriceEventSource
01/25/2019$1,600,000Sold
N/A
11/02/2017$5,000ListingRemovedAgent Provided
06/09/2017$5,000Listed For RentAgent Provided

Market trends in Roxbury

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
2MoM
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Property Tax and Assessment

Year2025
Tax$8,153
Assessment$627,130
Home facts updated by county records

Comparable Sales for 357 Painter Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
253 Tophet Road, Roxbury, CT
0.60
Single-Family Home
$1,500,000
11/18/25
4
3.5
2,437
277 Painter Hill Road, Roxbury, CT
0.65
Single-Family Home
$2,547,500
01/30/26
3
2.5
2,559
76 Cross Brook Rd, Roxbury, CT
0.43
Single-Family Home
$850,000
03/11/26
3
2
1,371
123 Cross Brook Road, Woodbury, CT
0.36
Single-Family Home
$590,000
06/17/26
1
2
1,564
247 Painter Hill Rd, Roxbury, CT
0.95
Single-Family Home
$1,375,000
03/27/26
4
4
2,396
158 Painter Hill Road, Roxbury, CT
1.45
Single-Family Home
$1,195,000
11/07/25
3
2.5
2,793
63 West Mountain Road, Washington, CT
1.46
Single-Family Home
$2,195,000
05/01/26
4
4.5
3,699
187 Painter Hill Rd, Roxbury, CT
1.42
Single-Family Home
$1,133,000
08/21/25
4
3.5
3,155
7 Jonathan Dr, Roxbury, CT
1.66
Single-Family Home
$1,050,000
12/09/25
3
3
1,976
158 Hazel Plain Road, Woodbury, CT
1.27
Single-Family Home
$424,950
10/23/25
4
2.5
2,085

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Assigned Schools

These are the assigned schools for 357 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
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  • 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 357 Painter Hill Rd

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Off Market Homes Near 357 Painter Hill Rd

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