29 Jonathan Dr, Roxbury, CT 06783
Property image
Property image
OFF MARKET

$599,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,806 sqft (on 2.28 acres)

29 Jonathan Dr, Roxbury, CT 06783

Est. Refi. Payment $4,170/mo*
Refinance Your Home
Currently Off Market - Sold Nov 17, 2015 for $225,000

Home Value

Trulia Estimate
$599K
Since last month
Increased$26K (+4.5%)
Since last year
Increased$32K (+5.5%)
Since last sale
Increased$379K (+168.3%)
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 +170% in the last 10 years
MonthEstimated value
2026
September 2026$604K
August 2026$578K
July 2026$603K
June 2026$621K
May 2026$600K
April 2026$585K
March 2026$586K
February 2026$564K
January 2026$554K
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
0.15
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
0.21
Single-Family Home
$1,050,000
12/09/25
3
3
1,976
247 Painter Hill Rd, Roxbury, CT
0.59
Single-Family Home
$1,375,000
03/27/26
4
4
2,396
277 Painter Hill Road, Roxbury, CT
0.89
Single-Family Home
$2,547,500
01/30/26
3
2.5
2,559
158 Painter Hill Road, Roxbury, CT
0.92
Single-Family Home
$1,195,000
11/07/25
3
2.5
2,793
76 Cross Brook Rd, Roxbury, CT
1.36
Single-Family Home
$850,000
03/11/26
3
2
1,371
16 Orchard Lane, Washington, CT
1.36
Single-Family Home
$1,725,000
10/28/25
3
2
2,564
249 Woodbury Road, Washington, CT
1.54
Single-Family Home
$529,000
01/09/26
2
2
1,268
56 Goldmine Road, Roxbury, CT
1.42
Single-Family Home
$1,425,000
09/01/26
3
2.5
2,620

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
16 Jonathan Drive, Roxbury, CT 06783
0.12
$998,000
3
2.5
2,028
For Sale
137 Davenport Road, Roxbury, CT 06783
0.15
$455,000
3
2
1,614
Recently Sold
35 Painter Ridge Road, Roxbury, CT 06783
0.31
$1,664,400
2
3
2,799
Off Market
108 Davenport Road, Roxbury, CT 06783
0.43
$1,951,600
4
5.5
5,100
Off Market
76 Davenport Road, Roxbury, CT 06783
0.47
$1,330,400
2
3
2,445
Off Market
195 Painter Hill Road, Roxbury, CT 06783
0.45
$936,700
2
2.5
2,322
Off Market
2 Pickett Road, Roxbury, CT 06783
0.52
$1,799,000
5
4.5
3,326
For Sale
00 Pickett Road, Roxbury, CT 06783
0.53
-
-
-
-
Off Market
201 Painter Hill Road, Roxbury, CT 06783
0.52
$909,800
3
2
1,720
Off Market
220 Painter Hill Road, Roxbury, CT 06783
0.55
$2,750,000
4
4.5
4,570
For Sale
Painter Hill Road, Roxbury, CT 06783
0.55
-
-
-
-
Off Market
Painter Hill Road, Roxbury, CT 06783
0.55
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 29 Jonathan Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1981
2.28 acre lot
1,806 sqft
$332/sqft
Garage

About this House

This single-family home is located at 29 Jonathan Dr, Roxbury, CT. 29 Jonathan Dr is in Roxbury, CT and in ZIP code 06783. This property has 3 bedrooms, 2 bathrooms and approximately 1,806 sqft of floor space. This property has a lot size of 2.28 acres and was built in 1981.
29 Jonathan Dr, Roxbury, CT 06783 is a 3 bedroom, 2 bathroom, 1,806 sqft single-family home built in 1981. It last sold for $225,000 on Nov 17, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $599,300, with a rent estimate of $3,583/month.

Home Details for 29 Jonathan Dr

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating 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: 1981Year Updated: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.28 acres

Price and Tax history

DateEventPrice
Nov 17, 2015
Source: N/A
Sold
$225,000
Sep 22, 2015
Source: Agent Provided
Pending
$249,000
Jul 20, 2015
Source: Agent Provided
PriceChange
$249,000
Price decreased by 9%
Jul 6, 2015
Source: Agent Provided
Listed For Sale
$275,000
Mar 6, 2013
Source: N/A
Sold
$100,000

Market trends in Roxbury

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
33
1MoM

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 29 Jonathan Dr

  • What is 29 Jonathan Dr estimated to be worth?
    Trulia's estimated value for 29 Jonathan Dr in Roxbury, CT is $599,300.
  • What is the price history for 29 Jonathan Dr?
    29 Jonathan Dr in Roxbury, CT last sold for $225,000 in November 2015.
  • Is Roxbury a buyer's or seller's market?
    Roxbury is currently a seller's market, based on recent for-sale activity.
  • What are the closest schools to 29 Jonathan Dr?
    The closest schools to 29 Jonathan Dr in Roxbury, CT are Booth Free School (Elementary), Shepaug Valley School (Middle/High, rated 8/10).
  • How big is the lot at 29 Jonathan Dr?
    The lot at 29 Jonathan Dr in Roxbury, CT is about 2.3 acres.
  • Does 29 Jonathan Dr have a garage?
    Yes, 29 Jonathan Dr in Roxbury, CT has a garage.

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 29 Jonathan Dr

Skip to last item
Skip to first item

Homes for sale near 29 Jonathan Dr

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item