8 Jonathan Dr, Roxbury, CT 06783
OFF MARKET

$741,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,499 sqft (on 2.44 acres)

8 Jonathan Dr, Roxbury, CT 06783

Est. Refi. Payment $4,943/mo*
Refinance Your Home
Currently Off Market - Sold Mar 14, 2018 for $286,650

Home Value

Trulia Estimate
$741K
Since last month
Increased$11K (+1.5%)
Since last year
Increased$62K (+9.2%)
Since last sale
Increased$450K (+157%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +80% in the last 10 years
MonthEstimated value
2026
August 2026$737K
July 2026$726K
June 2026$746K
May 2026$723K
April 2026$706K
March 2026$692K
February 2026$681K
January 2026$664K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
137 Davenport Road, Roxbury, CT
0.09
Single-Family Home
$455,000
08/18/26
3
2
1,614
17 Jonathan Dr, Roxbury, CT
0.14
Single-Family Home
$900,000
05/12/26
3
2
1,768
7 Jonathan Dr, Roxbury, CT
0.09
Single-Family Home
$1,050,000
12/09/25
3
3
1,976
247 Painter Hill Rd, Roxbury, CT
0.73
Single-Family Home
$1,375,000
03/27/26
4
4
2,396
322 North Street, Roxbury, CT
1.02
Single-Family Home
$500,000
09/05/25
3
2
1,397
16 Orchard Lane, Washington, CT
1.23
Single-Family Home
$1,725,000
10/28/25
3
2
2,564
277 Painter Hill Road, Roxbury, CT
1.01
Single-Family Home
$2,547,500
01/30/26
3
2.5
2,559
158 Painter Hill Road, Roxbury, CT
1.11
Single-Family Home
$1,195,000
11/07/25
3
2.5
2,793
76 Cross Brook Rd, Roxbury, CT
1.49
Single-Family Home
$850,000
03/11/26
3
2
1,371
249 Woodbury Road, Washington, CT
1.37
Single-Family Home
$529,000
01/09/26
2
2
1,268

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
137 Davenport Road, Roxbury, CT 06783
0.09
$455,000
3
2
1,614
Recently Sold
108 Davenport Road, Roxbury, CT 06783
0.27
$1,938,400
4
5.5
5,100
Off Market
2 Pickett Road, Roxbury, CT 06783
0.34
$1,799,000
5
4.5
3,326
For Sale
00 Pickett Road, Roxbury, CT 06783
0.35
-
-
-
-
Off Market
35 Painter Ridge Road, Roxbury, CT 06783
0.39
$1,684,700
2
3
2,799
Off Market
76 Davenport Road, Roxbury, CT 06783
0.40
$1,311,800
2
3
2,445
Off Market
62 Davenport Road, Roxbury, CT 06783
0.61
$5,646,200
4
5
6,228
Off Market
195 Painter Hill Road, Roxbury, CT 06783
0.64
$925,500
2
2.5
2,322
Off Market
Painter Hill Road, Roxbury, CT 06783
0.71
-
-
-
-
Off Market
Painter Hill Road, Roxbury, CT 06783
0.71
-
-
-
-
Off Market
201 Painter Hill Road, Roxbury, CT 06783
0.71
$903,600
3
2
1,720
Off Market
220 Painter Hill Road, Roxbury, CT 06783
0.73
$2,750,000
4
4.5
4,570
For Sale

Local Information

  • Map ViewExplore the area around 8 Jonathan Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1984
Lot Size
2.44 acres
Living Area
2,499 sqft
Price/Sqft
$297
Parking
Garage

About this House

Classic 3 Bedroom cape in one of Roxbury's most established rural neighborhoods within walking distance of Shepaug High School. One bedroom on main floor and two up. All are spacious. Living room with fireplace. Family room with cathedral ceiling opens to terrace. The house sits back from the road and has a distant view. Roxbury residents have use of Shepaug's tennis courts and indoor pool.
8 Jonathan Dr, Roxbury, CT 06783 is a 3 bedroom, 2 bathroom, 2,499 sqft single-family home built in 1984. It last sold for $286,650 on Mar 14, 2018. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $741,300, with a rent estimate of $4,272/month.

Home Details for 8 Jonathan Dr

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Forced Air, OilHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1984Year Updated: 2000
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 2.44 acres

Price and Tax history

DateEventPrice
Mar 14, 2018
Source: N/A
Sold
$286,650
Oct 20, 2017
Source: Agent Provided
PriceChange
$303,000
Price decreased by 12%
May 17, 2017
Source: Agent Provided
PriceChange
$344,000
Price decreased by 1%
Apr 3, 2017
Source: Agent Provided
PriceChange
$349,000
Price decreased by 8%
Mar 27, 2017
Source: Agent Provided
Listed For Sale
$379,000

Market trends in Roxbury

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32

Around this home

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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 8 Jonathan Dr

  • What is 8 Jonathan Dr estimated to be worth?
    Trulia's estimated value for 8 Jonathan Dr in Roxbury, CT is $741,300.
  • What is the price history for 8 Jonathan Dr?
    8 Jonathan Dr in Roxbury, CT last sold for $286,650 in March 2018.
  • Is Roxbury a buyer's or seller's market?
    Roxbury is currently a balanced market, based on recent for-sale activity.
  • What are the closest schools to 8 Jonathan Dr?
    The closest schools to 8 Jonathan Dr in Roxbury, CT are Booth Free School (Elementary), Shepaug Valley School (Middle/High, rated 8/10).
  • How big is the lot at 8 Jonathan Dr?
    The lot at 8 Jonathan Dr in Roxbury, CT is about 2.4 acres.
  • Does 8 Jonathan Dr have a garage?
    Yes, 8 Jonathan Dr in Roxbury, CT has a garage.

Apartments for Rent

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Off Market Homes Near 8 Jonathan Dr

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